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Every Sean Connery Movie Ranked Worst To Best

Forever known as Bond ... James Bond, Hollywood legend Sean Connery got his start in a handful of dramas and comedies before slipping into a tuxedo to play the world's most iconic super spy. But while his biggest role cemented him as one of the industry's sexiest leading men, he made a name for himself beyond 007, too. From his collaborations with celebrated director Sidney Lumet, to his turn as King Arthur of Camelot, Connery was never hesitant to experiment with new genres and different roles during his more than 50 year career.

He starred in a forgotten Disney classic and an unforgettable Hitchcock mystery; a disastrous superhero team-up, an award-winning gangster movie, and a number of high-stakes political thrillers. He's worked alongside some of the biggest Hollywood stars, and played mentor to both an immortal warrior and whip-cracking adventurer.

From James Bond to Indiana Jones, we've ranked every Sean Connery film from worst to best. Think you know what tops the list? It just might surprise you. Read on to find out for yourself.

55. The Avengers (1998)

In the '90s, making big budget Hollywood adaptations of old 1960s TV shows seemed to be all the rage, with "Lost In Space," "Mr. Magoo," and others. Sean Connery took a shot at one himself, starring as the villain in the 1998 adaptation of the hit 1960s British action spy series "The Avengers." Starring Ralph Fiennes and Uma Thurman as secret agents John Steed and Emma Peel, it saw Connery flip the script to play the would-be world-conquering villain battled by super-spies. Here he starred as the wicked baddie Sir August de Wynter, a mad scientist who creates a weather control machine to terrorize the planet.

Despite its all-star cast and big budget, the movie was an absolute disaster from every conceivable angle. It bombed at the box office and was thrashed by critics, with the Washington Post saying "[its] badness is banal ... not enough wit, too much money, no clear tone, no confidence, nothing to say." It failed to become the next big action spy franchise that it aspired to be, and made Connery the butt of many jokes for his buffoonish performance as a live action cartoon super-villain. 

54. Sword Of The Valiant

In "Sword Of The Valiant," Connery plays the Green Knight, a mysterious other-worldly figure who challenges King Arthur's court to a deadly duel, with only the young Sir Gawain stepping forward to accept. When the Green Knight is beheaded, but survives the decapitation, he promises to return to strike Gawain down, but gives the young knight the chance to save himself by solving a confounding riddle.

Inspired by the Middle English poem "Sir Gawain and the Green Knight," the 1984 film once again saw Connery hopping aboard a trend, this time the fantasy film boom of the mid '80s. But "Sword Of The Valiant" was no "Legend" or "Labyrinth." Directed by Stephen Weeks, the film was a remake of the 1974 effort "Sir Gawain And The Green Knight," also directed by Weeks. With Connery, Peter Cushing, and John Rhys-Davies, it had a better cast and more star power, but failed to deliver with lackluster special effects and a bizarre synth score.

53. The Next Man

Taking place in the midst of the Arab Oil Embargo of the early 1970s, when Arab nations boycotted those countriees supportive of Israel by blocking oil exports, "The Next Wave" saw Sean Connery play Saudi Arabian minister of state Khalil Abdul-Muhsen. Abdul-Muhsen has a bold proposal to ease tensions by recognizing Israel's statehood and offering his own country's rich oil deposits to smaller nations in dire need of the valuable resource. But his plan to support Israel makes him a number of enemies. 

The terrorists send a woman named Nicole Scott to infiltrate Abdul-Muhsen's office in an apparent assassination attempt, but things become complicated for her when she develops romantic feelings for him. A suspenseful political thriller, "The Next Man" was criticized for casting the Scottish Connery, who could not be believed as an Arab diplomat. From its poor casting to its dubious plot, it was butchered by reviewers on its release in 1976 and is no more loved today. 

52. Highlander II: The Quickening

The sequel to the 1986 science fiction fantasy film "Highlander," the followup, subtitled "The Quickening," once again stars Christopher Lambert and Sean Connery, but the results were far below what fans may have expected after the first film. "Highlander: The Quickening" sees Connor MacLeod (Lambert) regaining his powers and attempting to stop an evil mega corporation who controls The Shield, a protective barrier around the Earth in 2024. Also starring Virginia Madsen, Michael Ironside, and John C. McGinley, it sounds interesting on paper but was a pale imitation of its predecessor.

In addition to its nonsensical plot, "Highlander II" feels almost disconnected from the first film, rewriting much of the established backstory, and has become a black mark on a long-running franchise. The film was so poorly received that a third film, "Highlander III: The Sorcerer" almost entirely ignores "The Quickening," with many fans considering it the proper sequel.

51. A Good Man In Africa

Decried for its not-so-subtle racism and backwards attitudes, "A Good Man In Africa" is set in a fictional African province that's recently gained its independence from British rule. A British diplomat — the hard-drinking, womanizing Morgan Leafy (Colin Friels) — is eager to back to his home isles, but must deal with one last crisis before he departs. When an oil deposit is discovered in the region, he and his colleague Fanshawe (John Lithgow) must negotiate with the African nation's soon-to-be-elected President Adekunle (Louis Gossett Jr.). 

But when a young girl is struck by lighting and ritual customs require dealing with it in a specific manner, it causes trouble for them. Connery stars as Alex Murray, the British doctor tasked with helping Leafy, and supposedly the only man with any moral compunction among them. Though lambasted by critics for its complicated and politically incorrect tone, as well as the awkward and uncomfortable story, Connery did receive praise for his charming performance as the character referenced in the title.

50. Meteor

Sean Connery broke into the '70s disaster movie craze with the late-decade entry, "Meteor" starring a number of Hollywood icons like Natalie Wood, Martin Landau, and Henry Fonda. Loosely inspired by the 1967 MIT scientific report "Project Icarus," the movie saw Earth's astronomers discovering a massive five-mile wide asteroid fragment — nicknamed Orpheus — on a direct collision course with Earth. Capable of wiping out all life on the planet, Earth is bombarded first by a series of smaller meteors that create a multitude of cataclysms across the globe, all while politicians argue over how to deal with the impending world-ending threat.

Dr. Paul Bradley (Connery), however, had already designed a nuclear missile platform for just such an event, but it's since been co-opted as a terrestrial weapon to defend against foreign adversaries. But even if they can redirect it towards Orpheus, they'll have to work with their counterparts in the Soviet Union to do it, and it still may not be enough to stop it. Despite a Cold War angle that gave the disaster movie a unique spin, the movie was wholly unremarkable, lacking suspense, with no interesting characters, nor anything resembling the impressive special effects that a movie of its type requires.

49. Shalako

The only true Western in Connery's prolific filmography, "Shalako" saw the Scotsman anachronistically take on the role of title character, a grizzled veteran of the US Cavalry. The movie begins with a group of aristocratic English trophy hunters traveling the American frontier of New Mexico, when then become the targets of the Apache. The young and beautiful countess accompanying their group (played by '60s bombshell Brigette Bardot) is taken captive and rescued by a renegade gunslinger named Shalako (Connery).

Shalako attempts to help save the party from more attacks, but the arrogant and pretentious leader of the group doesn't want to listen. The hunting party soon finds themselves in way over their head, and it's up to Shalako to save them from their own hubris. Filled with unimpressive and "routine action" (per Roger Ebert) that failed to impress, "Shalako" is a forgettable Western, notable only for seeing the famed Scot playing a cowboy. It was also his only on-screen collaboration between he and Bardot, which was rumored to be fraught with tension.

48. Cuba

"Cuba" tells the story of the days just before the revolution on the island nation. Sean Connery stars as a British mercenary called Robert Dapes. Arriving in Havana, Dapes is there to help the people prepare to fight in the upcoming rebellion against the tyrannical government, run by dictator Batista. But while there, he reconnects with an old love named Alexandra (Brooke Adams). Though she is now married to arrogant factory owner Juan Pulido (Chris Sarandon), Dapes and his former lover rekindle their romance behind Juan's back.

But after a worker's strike, Dapes becomes the target of Cuban rebels. When tensions between government and rebel forces increase and the revolution begins, Dapes must find a way out of the country, while trying to convince his beloved Alexandra to leave with him and abandon her life in Cuba. Directed by Richard Lester (who would go on to replace Richard Donner for "Superman II"), the film was a big disappointment, with Time Out describing the film in their retrospective review as an incoherent political love story.

47. The Terrorists / Ransom

The 1974 film "Ransom" (alternatively titled "The Terrorists" in some territories) starred Sean Connery as Colonel Nils Tahlvikthe, national head of security for a fictitious European nation who must rescue the British Ambassador, taken hostage by a group of terrorists. Tahlvikthe clashes with British officials — they want to capitulate to the terrorists, while he takes a hardline stance of non-negotiation. But a second crisis erupts at the capital city's airport when a plane is taken over by a second group of terrorists led by Ray Petrie (Ian McShane). 

When Petrie plots to have the British ambassador moved from his residence to his hijacked plane, Tahlvikthe realizes that there's more at work than a simple ransom demand. An ambitious action thriller, "Ransom" is ultimately just a run-of-the-mill action drama that would likely not even be worth watching without Connery in the lead role. Thanks to the former Bond star's strong performance. the film is saved from being little more than a Saturday afternoon movie of the week.

46. A Fine Madness

The 1966 comedy "A Fine Madness," based on the book by Elliot Baker, was made just as Connery was becoming a major movie star thanks to his role as James Bond. Here he takes a break from playing a suave secret agent and stars as Samson Shillitoe, a poet and womanizer who is struggling to complete his latest work. But his problems go beyond his writer's block, as Shillitoe is hounded by a diligent debt collector after missing a number of alimony payments owed to his ex-wife. He soon loses his day-job as an office cleaner following a dalliance with an office secretary.

Eventually, Shillitoe gets help when his girlfriend Rhoda (Joanne Woodward) arranges for him to see a celebrated psychiatrist named Dr. West (Patrick O'Neill) who believes he can help him. But before long, West admits the poet to a sanitarium, where he becomes the subject of experiments by a staff doctor (Clive Revill) — all while Shillitoe begins an ongoing illicit relationship with West's wife Lydia (Jean Seberg).

45. Family Business

A neo-noir crime comedy, Sean Connery starred in the 1989 film "Family Business" as mafia family patriarch Jessie McMullen, who came to American shores in the 1940s and founded his family's criminal empire. Son Vito (Dustin Hoffman) followed in his father's footsteps, but left the family business after the birth of his own son Adam (Matthew Broderick). But Adam comes to admire and look up to his grandfather, and when he comes of age, finds himself disillusioned with his ordinary future, and is drawn back into the family business. 

Now with his father and grandfather, three generations scheme to pull off a daring heist. But when their best laid plans go disastrously wrong, it threatens to pull the entire family apart. Though it tries to be a heartfelt generational crime drama, it doesn't succeed. Despite the strong cast though, the old school caper film disappointed, with the New York Times noting the fine actors involved simply "[had] nothing to work with."

44. The League Of Extraordinary Gentleman

The 2003 sci-fi adventure movie "League Of Extraordinary Gentleman" is based on the acclaimed graphic novel by "Watchmen" writer Alan Moore. Set in the 19th century, the story sees the protagonists from a number of different and unconnected fictional literary works teaming up as a quasi-superhero team. Sean Connery plays Allan Quatermain, star of the novel "King Solomon's Mine," and is joined by Captain Nemo (Naseeruddin Shah), Dorian Gray (Stuart Townsend), Tom Sawyer (Shane West), Dr. Jekyll (Jason Flemyng), and Mina Harker (Peta Wilson) as they do battle with the nefarious Professor Moriarty (Richard Roxburgh). 

It was a clever premise, and adapted into a big budget movie with Connery taking top billing it must have seemed like a franchise in the making. Unfortunately, it proved to be less than the sum of its parts. It was a total disaster, and was the actor's final on-screen performance, as he stepped away from acting not long after its release. With the rise of superhero team-up blockbusters like "The Avengers" and "Justice League" in recent years, perhaps this one would have been better served if it had waited a couple of decades.

43. Wrong Is Right

The 1982 political satire "Wrong Is Right" put Sean Connery into the unexpected role of a hard-nosed but sardonic TV news reporter. Perhaps a bit too ahead of its time, the film shows a dark and disturbing future where sex and violence are glorified and the nightly news has become little more than sensationalistic tabloid fare. Connery is Patrick Hale, host of one of the country's highest rated news program — one that peddles the most outrageous stories and opinion news. Sent overseas to interview a foreign leader, he soon uncovers a nuclear bomb plot that threatens the United States, and a President who doesn't seem to know how to handle it. 

The apocalyptic black comedy wasn't well-received, with the New York Times commenting on the lame attempts at comedy and a plot that didn't stack up. But Connery himself managed to turn in a strong performance, with Time Out giving him high marks, but noting that the "ham-fisted nuclear blackmail thriller" didn't give him enough to work with. 

42. Operation Snafu / On The Fiddle

Released as "Operation Snafu" in the United States, the 1961 British comedy "On The Fiddle" starred a pre-Bond Sean Connery just a year before "Dr. No." But far from the dashing, debonair secret agent, the actor is instead the bumbling Horace Pope, a small time hustler arrested for street peddling. To get out of a jail sentence, Pope pretends he's just about to enlist in the army, and suddenly he finds himself shipping out to the Royal Air Force.

But seeing as it's in the middle of World War II, Pope does whatever he can to avoid being sent into action. He teams up with another misanthrope, Pedlar Pascoe, to plot and scheme their way into easier assignments far from the front. Eventually though, the two find themselves in Occupied France, where they find new ways to scam the locals while they stumble their way into becoming unwitting war heroes.

41. Zardoz

In perhaps one of his most infamous films, Sean Connery stars in the 1981 science fiction cult classic "Zardoz." Set in a far-out post apocalyptic future world where the Earth is ruled by an immortal race called the Eternals, whose tyrannical rule sees them lord over a lesser race of human warriors called the Brutals. Worshipping the Eternals' artificial stone god Zardoz, the Brutals live in an oppressed society until one man, a Brutal named Zed (Sean Connery) fights back.

With mutton chops, a thick bushy mustached and clad in a red diaper and knee high boots, Zed sets out to discover the truth of the Eternals and lead a Brutal rebellion. Perhaps one of the most bizarre science fiction films ever made, "Zardoz" has become a bona fide cult classic by fans who appreciate it for all of its weirdness, including its dream-like opening sequence that depicts a stone deity vomiting guns and ammo.

40. Another Time, Another Place

Based on the 1955 Lenore J. Coffee novel "Weep No More," Sean Connery appeared in "Another Time, Another Place" in 1958, a British drama about a London reporter in the final years of the Second World War. The film stars Lana Turner ("The Postman Always Rings Twice") as Sarah Scott, American journalist in London who begins an affair with local reporter Mark Trevor (Connery). 

After leaving her boyfriend in New York to be with Trevor, she's devastating to learn that he is married and has a family at home. But when Trevor is killed, Scott goes to work for his widow Kay under the auspices of turning his final work into a book. As she grows closer to Kay and Trevor's children she must decide whether to reveal the truth about her relationship with him to his surviving family. 

An effective melodrama, "Another Town, Another Place" might be most notable for an incident involving Turner's real life mobster boyfriend threatening star Connery for his rumored love affair with Turner.

39. Five Days One Summer

Set in the 1930s, Sean Connery plays an aging doctor named Douglas Meredith, matched with a woman more than half his age — the charming and beautiful Kate (Betsy Brantly) — whom he is taking on a trip to the Swiss Alps. However, there's much more controversy to their relationship than the large age difference, and its revealed that their trip is actually their first time away together from the prying eyes of their judgmental family. 

But while Douglas begins spending time to himself during their retreat, Kate is off getting to know the charming young man who has been their tour guide: the dashing, younger Johann Biari (Lambert Wilson). As their feelings grow, Biari learns of the true nature of Kate's relationship with her much older lover, and tries convincing her to leave Douglas for him. Caught in between her heart and her head, Kate is conflicted, but while out on a mountain climb together, the rivalry between Douglas and Biari suddenly becomes dangerous. 

A box office bomb, "Five Days One Summer" is a trite melodrama that hasn't aged well, and will likely make modern audiences cringe.

38. The Presidio

The 1988 police drama "The Presidio" starred Mark Harmon as a San Francisco detective Jay Austin, whose former partner in the military police is killed in the line of duty. Taking the case, Austin returns to his old stomping grounds and encounters his old commander, Lieutenant Colonel Alan Caldwell (Sean Connery), with whom he has a bitter and contentious relationship. But now the two must put aside their differences and work together to find a killer.

The investigation leads them to an officer Austin once suspected in another murder, on the same case that Caldwell had once demoted him for investigating. As the current investigation proceeds, secrets are uncovered, but their relationship is troubled when Austin falls in love with Caldwell's daughter (Meg Ryan). Though it doesn't have the sharpest script, it's a relatively effective, slickly produced crime drama with a good cast, and Connery delivers another fine performance as the complicated Caldwell.

37. First Knight

After being miscast as the ghostly villain in an Arthurian legend once before in "Sword Of The Valiant," the medieval drama "First Knight" saw Connery take on the role that was tailor made for him: That of the majestic Camelot ruler himself, King Arthur. Richard Gere and Julia Ormond played Sir Lancelot and Guinevere in a modern day take on the classic legend that eschewed the magical elements and opts for gritty, more grounded and realistic take on the Middle Age myth.

Unfortunately, despite Connery's impressive take on the Arthurian King, the film didn't compare favorably to others in the genre. Gere, as the lead of the film, was woefully miscast, while the film itself lacked the charms of other similar movies that might have made up for it. Still, "First Knight" was a modest box office success, and generated a handful of good reviews. It's not the worst take on the legend, and might be a worthy decent for fans of the former Bond star.

36. Medicine Man

The 1992 drama "Medicine Man" sees Sean Connery in the role of Dr. Robert Campbell, an eccentric scientist who has lived more than half a decade in the Amazon searching for a cure for cancer. Believing he's made a breakthrough, a pharmaceutical company sends Dr. Rae Crane (Lorraine Bracco) to check up on his progress. Campbell is resentful of his new partner and hesitant to work with her, but eventually the two continue their research and discover a rare compound that could be just what they're looking for.

But when a logging company begins to encroach on their remote village it threatens to undo all of their work. Now it's a race against time to uncover the secrets of a rare jungle flower, and crack the code that could save millions of lives. Whether it was incorrectly marketed as an adventure movie, or because it really wasn't very good, critics didn't give "Medicine Man" a warm reception, with Roger Ebert saying that despite having all the ingredients "for a movie I would probably enjoy very much ... they never come together." 

35. Rising Sun

Based on the novel by Michael Crichton, the 1993 action thriller "Rising Sun" released the same summer as another Crichton-penned blockbuster, "Jurassic Park." This one, released just a year after the novel hit shelves, features a screenplay by the author himself, and stars Wesley Snipes, Sean Connery, Harvey Keitel, and Cary-Hiroyuki Tagawa. Snipes and Connery play a pair of Los Angeles detectives called in to investigate the body of a sex worker found in the offices of a Japanese conglomerate. Despite a clash of cultures, the investigation proceeds, with evidence turning up in the form of a disc loaded with security footage that reveals their suspect.

But things take a turn when it's revealed that the footage itself may have been digitally altered, and the detectives soon realize that dangerous new technologies could help a murderer go free. A smart, stylish thriller, it's an engrossing crime drama let down by a script that loses a lot of what made it great during its translation to the screen.

34. The Russia House

"The Russia House" is a 1989 Cold War political thriller based on the novel by John le Carré ("The Spy Who Came In From The Cold"). The film stars Sean Connery as British publisher Barley Scott-Blair, who is given a manuscript for a new book by a mysterious young Russian woman named Katya Orlova (Michelle Pfeiffer). But when its discovered that the manuscript may document the Soviet Union's entire nuclear missile program — its status, its capabilities, and even its weaknesses — he suddenly becomes a crucial asset for both Britain's intelligence service MI6, and the American CIA.

Concerned that Barley may also be a target of Russian forces, the CIA assigns their own agent (Roy Scheider) to work with him as he meets with Katya to track down the book's author and confirm the authenticity of its contents. But when Barley and Katya become romantically involved, he finds himself emotionally compromised — and deeper in the covert operation than he ever realized.

33. The Frightened City

The 1961 film noir gangster flick "The Frightened City" starred a young Sean Connery in the uncharacteristic role as a small time crook. The film begins with a night club owner who is running a protection racket under the table. His accountant proposes they broaden their business across greater London, but need a strong arm to be their collection agent. Enter Paddy Damion, a small-time Irish burglar played with aplomb by Scotsman Sean Connery. In need of cash after his criminal cohort is wounded in a botched robbery, Paddy takes the job and becomes an important part of a sprawling criminal enterprise.

Though no all-time classic, "The Frightened City" is a fun if ordinary crime drama with Sean Connery in a standout performance. Variety's review called it "a conventional but brisk gangster yarn," and gave Connery praise, sating "newcomer, rugged Sean Connery makes a distinct impression as an Irish crook, with an eye for the ladies." Given that endorsement, it's no wonder he'd be cast as Britain's greatest secret agent a year later in "Dr. No."

32. Dragonheart

The family fantasy film "Dragonheart" introduced a new generation to the talents of Hollywood legend Sean Connery, this time through his distinctive voice. In "Dragonheart," Connery provides the voice and personality for the fun-loving, adventure-seeking dragon named Draco. The film stars Dennis Quaid as legendary dragon killer who initially sets out to kill Draco, the last dragon, but instead forms an unlikely friendship with him. Together they craft a scheme to collect money from unknowing townspeople, with Draco pretending to terrorize a village, and Bowen paid to rid the town of the dragon menace. 

But when Bowen agrees to help Kara overthrow the tyrannical King Einon, his former protegee, he learns that Draco and the King are connected. To save Einon's life, Draco had given him a piece of his heart, and now if Einon dies, so too will Draco. Thanks to a combination of cutting edge CGI by George Lucas' Industrial Light & Magic and the voice work of Connery, the film became a beloved '90s fantasy adventure that spawned a series of direct-to-video sequels, with the likes of Ben Kingsley and Patrick Stewart acting as stand-ins for Connery.

31. Entrapment

In one of the actor's final films, Sean Connery would return to the spy thriller genre in "Entrapment," a mind-bending heist film that takes place at that dawn of the new millennium. Catherine Zeta-Jones stars as Gin, a supposed investigator out to catch renowned art thief Robert "Mac" MacDougal, who is the prime suspect in the theft of a priceless painting from a New York City skyscraper. Posing as a fellow thief, Gin proposes they attempt a daring heist, leading to a plot to defraud an international bank of $8 billion. 

The action-packed thriller plays a number of classic spy games as allegiances are questioned, and agents double and triple cross one another. In the end, "Entrapment" is an exciting, big budget espionage adventure, a modern update to spy classics of old. Roger Ebert, among many reviewers, praised the film, saying it was "the very embodiment of a star vehicle: a movie with a preposterous plot, exotic locations, absurd action sequences, and so much chemistry between attractive actors that we don't care." He lauded Connery for his ability to deliver ludicrous dialogue that only an actor of his caliber could get away with.

30. Outland

Often described as a space western, you might be fooled by posters and stills into thinking this was a contemporary cop drama. Instead, "Outland" is a science fiction adventure set in a bleak future world, where Earth has colonized other planets and is run mostly by cold corporations. On one of the moons of Jupiter, Federal Marshal William O'Niel is assigned to patrol a titanium mine after a series of inexplicable deaths of the company's overworked employed. In his investigations, O'Niel is joined by company doctor Marian Lazarus (Frances Sternhagen), and its not long before they uncover a web of conspiracies that reach all the way to the top.

Though not his first — or last — science fiction film, "Outland" is probably Connery's best in the genre. Though no classic, it's become something of a cult favorite among sci-fi buffs, with a tone reminiscent of films like "Alien" or "Blade Runner." It was a box office flop in 1981, and critics gave it mixed reviews, but a more recent look back by JoBlo called "Outland" a "forgotten gem."

29. Just Cause

In this 1995 legal thriller, Sean Connery plays Paul Armstrong, a Harvard law professor fiercely against capital punishment. He also has a reputation for fighting death penalty cases and successfully keeping his clients out of the electric chair. He's asked to help with the case against Bobby Earl Furguson (Blair Underwood), who sits on death row and whose mother insists he's been wrongfully convicted of murder. The case hinges on a faulty confession obtained through the use of force by local cop Tanny Brown (Laurence Fishburne), who is now the town's sheriff.

As Armstrong interviews Furguson, and then Brown, he becomes convinced that the Furguson is innocent, and zeroes in on a convicted murder (Ed Harris) as the real killer. But as more information comes to light, the more Armstrong begins to doubt everything about the case. A classic murder mystery with a shocking twist, "Just Cause" is an effectively suspenseful thriller. Kate Capshaw ("The Temple Of Doom"), Scarlett Johansson ("Black Widow") and Ned Beatty ("All The President's Men") also star.

28. The Woman Of Straw

Adapted from the 1954 novel "La Femme de paille" by Catherine Arley, "The Woman Of Straw" sees Sean Connery playing wealthy socialite Tony Richmond. Richmond's wheelchair-bound uncle — the cruel and overbearing millionaire Charles (Ralph Richardson) — is nearing the end of his days and has decided to give his entire estate and his vast fortune to charity. Tony has other ideas, and introduces his uncle to a young and beautiful nurse named Maria (Gina Lollabrigida), who he's instructed to beguile the dying magnate in the hopes they will marry and she can inherit his millions.

But while Tony has arranged with Maria that they'll split the inheritance after Charles' death, his plan goes awry when she begins to have real feelings for his dying uncle. And when he passes, it's not long before some believe it may have been foul play, and Maria is the first suspect on the list. Better reviewed today than on its release, retrospective reviews have found it an intriguing detective story.

27. Playing By Heart

"Playing By Heart" follows nearly a dozen seemingly unconnected characters living in and around Los Angeles as they navigate the ups and downs of life and love. A broad cast, it features Sean Connery and Gena Rowlands as an aging couple who are planning to renew their wedding vows after the discovery that Connery's character has terminal cancer. The rest of the coupled cast includes Angelina Jolie and Ryan Phillipe, Randy Quaid and Madeline Stowe, and Gillian Anderson and Jon Stewart. Each couple finds themselves dealing with different problems in their unique relationships.

Though at first the film makes it seem these pairings are all random, unrelated people, they are slowly revealed to be connected as the movie progresses. A spiritual precursor to Garry Marshall's Holiday trilogy, Roger Ebert called it a "near-miss" while acknowledging it was a likable movie with charming moments. The New York Times was far kinder to the film, saying it "percolates with an earnest charm," and calling it a "comedy set in an urban lotus land where every morning promises a Valentine's Day surprise." 

26. The Molly Maguires

Inspired by the true story of a group of Pennsylvania coal miners in the 1870s in the days before unions, "The Molly Maguires" tells the story of a group of disgruntled laborers who band together to fight back against the brutality of the mining companies. Abused, overworked, and dying by the dozen, the rebel workers — led by a man named Jack Kehoe (Sean Connery) — wage an ongoing war with the mine's owners, sabotaging the subterranean tunnels with explosives. As the problems worsen, the Pinkerton Detective Agency sends James McParlan (Richard Harris) to the region to stop the Kehoe's campaign of terror.

To catch the ringleader of the Molly Maguires though, McParlan must go undercover and infiltrate their group. He poses as a man on the run from the law, and gets a job in the mines, slowly working his way into Kehoe's good graces, eventually joining him in his quest for social justice. But now that McParlan has befriended Pennsylvania coal miners, he'll have to betray them to do his job.

25. Highlander

Returning to the fantasy genre in 1986, Sean Connery would play a key supporting role in the adventure epic "Highlander." The movie starred Christopher Lambert as an immortal warrior named Connor MacLeod. Connery co-starred as the swordsman Juan Sánchez-Villalobos Ramírez, an immortal born centuries before in Egypt and who has made his way across the world. In Scotland, he encounters MacLeod, a younger immortal banished from his village after he miraculously heals from a fatal wound at the hands of the villain Kurgan — Ramírez's old foe.

Ramírez trains MacLeod and together they hope to find and defeat Kurgan. But in a duel, Ramírez is killed, and MacLeod takes up his mentor's sword and mantle, looking for vengeance. Though by all accounts it was a box office bomb, it grew a devoted fan following and garnered a number of sequels, a long-running television spin-off, an animated series, and a number of books, comics, and tie-in toys and board games. In his career, "Highlander" remains Sean Connery's only original film (the Bond movies were book adaptations) to have spawned its own mass media franchise.

24. The Anderson Tapes

Released the same year as his final appearance as James Bond in "Diamonds Are Forever" (before his later return, of course), the 1971 thriller "The Anderson Tapes" was helmed by renowned director Sidney Lumet ("12 Angry Men"). A classic heist film, it follows Connery as "Duke" Anderson, an expert safe cracker who's just been released from prison. Reconnecting with an old flame named Ingrid (Dyan Cannon), Anderson moves into her luxury apartment. The building is filled with wealthy tenants, giving him the perfect opportunity for another big score.

Bankrolled by a mob boss, Anderson recruits a crack team for the job. In addition to the usual assortment of varied criminal experts, Anderson's team also includes one thug he's been assigned to kill as part of his deal with the mob. But their plan to rob the building blind is complicated by an unfamiliar world of high tech surveillance, including closed circuit cameras and wiretaps, as he finds himself tracked by both a private detective and the FBI.

23. Robin And Marion

Directed by Richard Lester, the 1976 fairy tale adventure "Robin And Marion" put a new twist on the classic myth. It told the story of an older Robin Hood (played by Sean Connery) and his one true love, Maid Marion (Hollywood legend Audrey Hepburn). Robert Shaw, Nicol Williamson, Denholm Elliot, Ian Holm, and Richard Harris rounded out the cast. The story follows Robin Hood, now an older captain the King's guard, who even in his twilight years fights for good, refusing an order to sack a castle full of women and children. 

Reuniting with his band of merry men in Sherwood Forest, Robin reunites with Maid Marian, now a superior nun. But trouble strikes for them both when the Sheriff of Nottingham issues an order to arrest her, by decree from King John. Robin Hood once again comes to her rescue, setting them out on one last adventure together.

22. Never Say Never Again

For decades Connery, had insisted he'd never return to the role of James Bond, but the allure of one more shot as the secret agent — and a massive paycheck — got him back into the role for a last ride. "Never Say Never Again," titled as a meta reference to Connery's return, is largely a retelling of "Thunderball," and thus doesn't really provide much in the way of a fresh new story for Connery's Bond. Once again, a terrorist holds the world hostage, and 007 — long retired — must be reluctantly reinstated to stop them.

Despite being a common pick as the lowest rated of Connery's many Bond films, it's not without its considerable charm. The angle of an aged, past-his-prime MI6 agent offers an interesting twist. The star himself is as suave as ever in the role that made him a superstar, back in action for one more adventure. Even with its recycled plot, it still manages to provide action and excitement that fans of Bond in that era should appreciate.

21. Darby O'Gill And The Little People

Possibly one of Connery's least known films is the Disney family movie "Darby O'Gill And The Little People." The 1959 adventure sees the Scottish actor Connery playing a lad from Dublin named Michael McBride. In the film, McBride is brought in to take over for Darby O'Gill (Albert Sharpe), the aging caretaker of the estate of Lord Fitzpatrick (Walter Fitzgerald). Darby makes the young Dubliner promise not to tell his niece Katie he's been retired, so as not to upset her. 

But when Darby trips through a portal and enters a land of leprechauns, he meets the fantasy land's ruler King Brian, who follows him back through the portal onto the Fitzpatrick estate. Once he catches the leprechaun King, he's granted three wishes, and must be extra clever if he is to use them wisely. The rare Connery movie to feature a musical number, a memorable scene sees McBride singing a duet with Katie, though sadly it's not Connery's voice we hear, as he's instead dubbed over by crooner Ruby Murray (via Irish Times).

20. Diamonds Are Forever

Sean Connery's seventh and final film as James Bond before his return to the role more than a decade later, "Diamonds Are Forever" was a return of sorts as well. The previous film, "On Her Majesty's Secret Service" had starred George Lazenby, who replaced Connery for just a single film. For the follow-up, the studio lured Connery back to the series with a fat payday, which Connery promptly used to start a foundation for aspiring Scottish artists.

In the film of course, a new sinister villain hatches a plot to destroy Washington D.C. with a space-based weapons platform, and James Bond sets out to stop him. Filled with more over-the-top action than we've ever seen before, including a memorable sequence where Bond drives a buggy on the moon, "Diamonds Are Forever" may not be the simpler, retro spy thriller of old, but it still provides plenty of action and adventure as only a Bond movie can. Connery once again drew high marks for his performance as the suave secret agent, who is a little older, a little more seasoned, but no less slick and charming as he was in his earliest days.

19. The Wind And The Lion

The historical drama "The Wind And The Lion" was a movie very loosely based on the 1904 Perdicaris affair, which began when Moroccan chieftain Mulai Ahmed er Raisuli kidnapped a wealthy American citizen and their family. Sean Connery stars as the enigmatic chieftain Raisuli, who demands a ransom for the family in an effort to discredit his political opponents and spark a diplomatic crisis. Back in the United States, President Theodore Roosevelt intends to use the incident to show off his country's emerging status as a global military super power, in the hopes of improving his chances at re-election.

Written and directed by John Milius ("Apocalypse Now"), the film takes quite a few liberties with the historic account, but its Connery who impresses as the roguish, charismatic chieftain Raisuli. His dominating performance anchors the film, complimented by the lush visuals and a good mix of sweeping epic adventure and smart political thriller.

18. The Rock

In "The Rock," Michael Bay's second directorial effort, the bombastic filmmaker cast the legendary Sean Connery in the lead role of British Special Forces Captain John Patrick Mason. The only man ever to escape Alcatraz, the grimacing ex-soldier had stolen state secrets and spent the last 30 years in prison rather than give them up. But now he is recruited by the FBI to aid in a special operation to retake Alcatraz Island, after a team of traitorous military commanders overrun the prison and take more than 80 tourists hostage.

One of the best pure action films in Connery's filmography, the impressive cast includes Nicolas Cage, Ed Harris, Michael Biehn, and Tony Todd. A blockbuster in every sense, it's one of the actors biggest box office hits, and was a role that brought the actor back to his action hero roots. Over the years, fans have pointed out the many similarities between Mason and Connery's most famous movie role, with many believing he is actually intended to be an older version of 007 himself – even if the film couldn't legally say it.

17. A Bridge Too Far

The 1977 ensemble war film "A Bridge Too Far" was directed by Richard Attenborough and featured an expansive cast. Alongside Sean Connery the film featured James Caan, Michael Caine, Anthony Hopkins, Gene Hackman, Laurence Olivier, Robert Redford, Elliott Gould, Maximilian Schell, Ryan O'Neill, Denholm Elliott, and John Ratzenberger. It tells the story of Operation Market Garden, one of the most disastrous Allied efforts during the Second World War.

The film begins in 1944, with Sean Connery's General Urquhart planning to lead British and American forces on a daring mission to take a long stretch of road that leads into the heart of German territory. But the Allied forces soon discover that they may be in over their heads. Impressively shot, the film was applauded for its gritty realism, all-star cast, and vast scope.

16. The Name Of The Rose

Based on the debut novel by author Umberto Eco, the 1986 historical drama "The Name Of The Rose" starred Sean Connery, F. Murray Abraham, Christian Slater, and Ron Perlman. Connery starred as the eccentric 14th century Franciscan friar William of Baskerville, who is brought in to learn the truth behind a series of mysterious deaths that have occurred in a remote monastery. Learning that the deaths are murders, William suddenly realizes that he may be hunting a cold-blooded serial killer.

A historical murder mystery, "The Name Of The Rose" weaves a classic detective story through a period medieval drama. As William narrows down his suspects and collects evidence, new murders up the stakes. A deftly written suspense thriller that digs into old world politics, it's full of as many twists and turns as a good Agatha Christie novel. Though it wasn't a hit at the box office, it received mixed reviews in its day, but has seen a more positive response from critics looking back. It was remade in 2019 as a TV miniseries starring John Turtorro.

15. You Only Live Twice

James Bond returned in 1967 for Sean Connery's fifth turn in the role, you "You Only Live Twice," inspired by Ian Fleming's 1964 book. With a screenplay by Roald Dahl ("Charlie And The Chocolate Factory"), the film discarded the main story from the book and crafted something entirely new using the same characters. In the movie, set firmly in the midst of the Cold War, both the United States and the Soviet Union lose track of a spacecraft in Earth's orbit, and nuclear armageddon draws closer. 

British intelligence believes one of the missing craft may have landed off the coast of Japan, and sends James Bond to investigate. There he allies himself with Tiger Tanaka (Tetsuro Tamba) and Japanese bombshell Aki (Akiko Wakabayashi), where he learns that none other than Blofeld and SPECTRE may be involved in a plot to instigate a new world war. Following "You Only Live Twice," Connery would briefly retire from the role of 007, before returning in 1971 for "Diamonds Are Forever."

14. The Offence

As part of Connery's deal to return to the role of James Bond for "Diamonds Are Forever," the star would receive not just a big payout, but an agreement to star in two back-to-back films of his choice (via The Express). One of those would be "The Offence," directed by Sidney Lumet, who had helmed his previous non-Bond film "The Anderson Tapes." 

Eager to shed his secret agent image, Connery takes on the role of a police detective named Johnson, who kills a suspect during an interrogation. The film shows the complex ethical implications of his actions, as well as how he grapples with both the guilt and his own moral justifications. A deep and soulful morality play, "The Offence" was a long way from the action-packed spy adventures that audiences had become used to seeing Connery star in, and showed that he was capable of much more. 

13. The First Great Train Robbery

Connery seemed to love heist movies, and the 1978 film "The First Great Train Robbery" (released in the United States simply as "The Great Train Robbery") is a prime example. Written and directed by Michael Crichton ("Jurassic Park") and based on his own book of the same name, it also stars Donald Sutherland and Leslie-Anne Down. It is set in 1855, when traveling by locomotives was still in its relative infancy. Connery plays Edward Pierce, an well-respected member of London's social scene, who lives a secret double life as a master criminal. Looking for a new challenge, Pierce assembles a small team to attempt the unthinkable: robbing a heavily guarded moving train.

With a gold shipment on its way from London to the port city of Folkstone, Pierce devises a clever plan to break into the train and collect their prize. With two safes within, Pierce needs the help of a friendly pick-pocket and safe-cracker, his lovely mistress, and his loyal chauffeur. Loosely based on a real-life gold heist in 1855, "The First Great Train Robbery" may also be Connery's first great heist movie.

12. Thunderball

Connery returned as 007 in the fourth James Bond film, "Thunderball." Based on the novel by Ian Fleming of the same now, Bond has to stop the evil organization SPECTRE, who hijacked two nuclear warheads from NATO. SPECTRE threatens to unleash them on a major city somewhere in the United States or Great Britain if they're not paid a king's ransom in diamonds. Because of the threat to the US, bond is once again aided by CIA agent Felix Leiter (this time played by Rik Van Nutter), who plays a bigger role than in his previous appearances. 

Bond and Leiter track SPECTRE to the Bahamas, where they are planning to make the exchange. There, 007 matches wits with high-ranking enemy agent Emilio Largo, and his alluring mistress Domino. A classic Bond adventure, it may not be the best of the bunch, but it just might be the most fun, and full of many secret agent cliches when they were still fresh.

11. Marnie

In the middle of his James Bond days, Sean Connery took a detour to star in the romantic psychological thriller "Marnie" in 1964, directed by celebrated filmmaker Alfred Hitchcock. Starring Tippi Hedren as Marnie, we meet a mysterious young woman and con artist who has just stolen $10,000 and changed her name. Later, she goes to work for Mark Rutland (Sean Connery), a publishing magnate in Philadelphia, with her eyes set on another score. This time, though, Rutland recognizes the woman as a thief. But rather than have her arrested, Rutland wants to help the troubled woman. 

Eventually, the two fall in love and marry, but Marnie is haunted by nightmares, and Rutland becomes determined to unlock the secrets of her shadowy past. A gripping, tension-filled drama, Connery and Hedren's performances, along with Hitchcock's masterful direction, turn an otherwise outlandish premise into an effective mystery. Though it's not among the director's best films, it's certainly Connery's most impressive thriller.

10. Finding Forrester

In 2000, director Gus Van Sant ("Good Will Hunting") took another trip back to a school campus. In "Finding Forrester," Van Sant cast Sean Connery as reclusive author William Forrester, who discovers that a neighborhood teen named Jamal Wallace is a brilliant young writer. When Jamal is accepted into a prestigious Manhattan prep school on a basketball scholarship, the teen asks Forrester to mentor him and help with his writing, and the pair soon form a unique bond. 

Through their friendship, Jamal continues to become a better writer, and Forrester himself finds he has a renewed passion for his own work. But Jamal's promise to Forrester that he tell no one about their friendship is jeopardized when he is suspected of plagiarism, risking his scholarship if he doesn't tell his school board about the help he's been receiving. An inspiring and uplifting story of friendship and family, "Finding Forrester" impressed critics and became an unexpected hit.

9. Murder On The Orient Express

There have been several adaptations of the Agatha Christie classic "Murder On The Orient Express" over the years, and the 1974 film starring Albert Finney as Detective Hercule Poirot was the first to make it to the big screen. Connery starred as Colonel Arbuthnot, and the film teamed him with director Sidney Lumet for the third time. The movie follows the murder of a wealthy industrialist aboard a packed train, and the famed detective — who happens to be onboard — sets out to find the killer before they reach their destination.

Nominated for six Academy Awards, included Best Adapted Screenplay, it's still regarded as the best screen adaptation of Christie's novel, despite its flaws. Most of the criticism in fact lies with star Finney, who was not as faithful an interpretation of Poirot. Still, Roger Ebert loved it, saying it "provides a good time, high style, a loving salute to an earlier period of filmmaking."

8. The Hill

The first collaboration between director Sidney Lumet and Sean Connery, 1965's "The Hill" was set in British military prison in the Libyan desert at the tail end of the Second World War. There, a newly installed prison guard, the vicious Staff Sergeant Williams, subjects prisoners to extreme forms of punishment — each more brutal than the last. When five new detainees enter the prison, Williams gives them the worst treatment yet, forcing them to endure ceaseless climbs up a massive hill in the oppressive desert heat. 

Connery plays ex-Sergeant Major Joe Roberts, a prisoner convicted of assaulting his commanding officer. Roberts is tight-lipped about the incident, saying only that it was the result of defying an order to send his men on a hopeless mission. Roberts brings his defiance with him to the hill, clashes with Williams' increasingly tyrannical attitude, and is determined to stop him after the death of a fellow inmate.

7. The Hunt For Red October

The 1990 action flick "The Hunt For Red October" was the first movie adapted from a Tom Clancy novel, and the first appearance of Jack Ryan on screen. Directed by action movie veteran John McTiernan ("Die Hard," "Predator," and "Last Action Hero"), it stars Alec Baldwin as Ryan and Sean Connery as Marko Ramius, commander of the Russian stealth submarine Red October at the height of the Cold War in 1984. Ramius goes rogue and threatens the United States, leading CIA analyst Ryan to spearhead the effort to track him down.

Featuring an all-star cast, Ryan's supporting cast included James Earl Jones, Scott Glenn, and Courtney B. Vance, while Ramius' crew included Sam Neill, Stellan Skarsgård, and Tim Curry. A stunning thriller and a box office success, it spawned a veritable franchise for Jack Ryan, who would be subsequently played by Harrison Ford, Ben Affleck, Chris Pine, and more recently, John Krasinski. Despite making almost no effort to disguise his own accent, Connery was praised for his performance as the powerful Russian commander Ramius. 

6. Indiana Jones And The Last Crusade

The summer of 1989 was packed with blockbusters including Tim Burton's "Batman," "Back To The Future Part II," and "Ghostbusters II." Sean Connery joined the party, co-starring with Harrison Ford in the "Indiana Jones" threequel "The Last Crusade." Playing the adventuring father of the whip-wielding relic hunter Indiana Jones (Ford), the film kicks off when Connery's Henry Jones Sr. goes missing while on a search for the biblical Holy Grail, said to contain the secret to immortality. Picking up the search where his father had left off, Indiana Jones finds his dad held hostage by Nazis, who are intent on using the grail to help them take over the world.

Full of all of the same action, suspense, and fantasy adventure the series had become known for, Connery added a fresh new face to the franchise. His chemistry with Ford was electric, and the former Bond star proved that — decades later — he still had plenty of charisma to spare as an aging action hero. The biggest hit of 1989 behind only "Batman," it's sometimes cited as the best entry in the series, with much credit going to Connery's performance as the fatherly Jones.

5. The Untouchables

Adapted from the 1950s TV series starring Robert Stack, which in turn was based on the book of the same name, the 1989 Brian De Palma film "The Untouchables" told the real life story of the famed crime busting Prohibition agent Eliot Ness. Ness and his team of so-called "Untouchables," so named for their upstanding character and incorruptible nature, set out to take down notorious Chicago mob boss Al Capone. Led by Ness, the group also included disillusioned veteran cop Jim Malone (Sean Connery), a retired officer who is impressed enough with Ness' integrity to join his quest for justice. The impressive cast also included Robert De Niro as Capone.

Though it received mixed reviews upon its release by the likes of Roger Ebert, it has since become a classic gangster movie, in no small part thanks to the performances of its star-studded cast. Connery himself would take home his first and only Academy Award for his part as world-weary law enforcer Jim Malone.

4. Dr. No

The film that launched both James Bond and Sean Connery to fame, the 1962 film "Dr. No" set the bar by which all subsequent secret agent movies were to be judged. A groundbreaking spy thriller, it introduced Bond as a suave ladies man and ultra-capable British Intelligence agent. In his first adventure, Bond tracks down a missing rogue agent and discovers an insidious plot by a mysterious villain named Dr. No, who seeks to stop the launch of an American spacecraft.

A brilliant opening salvo in one of the movie industry's longest running franchises, it remains one of the best Bond movies to date. Far from the over-the-top adventures of later films in the series, "Dr. No" is a modest, understated spy drama, full of intense moments of espionage and detective work — punctuated by a handful of car chases and fisticuffs. It's impossible to overstate the importance of "Dr. No" in the pantheon of the genre, and the casting of Connery in particular, whose slick performance as Bond would be the standard for all who would follow.

3. From Russia With Love

After the success of "Dr. No," it didn't take long  before Sean Connery suited back up as the iconic British super-spy. The follow-up film "From Russia With Love" landed just a year later, and dealt with the direct aftermath of Bond's defeat of SPECTRE agent Dr. No. In one of the more complex Bond plots, the evil organization attempts to lure Bond into a trap using a beautiful female agent, who poses as a Russian defector and claims to possess a valuable decoding machine. Meanwhile, SPECTRE leader Kronsteen waits in the wings to execute his diabolical plans to spark a war between world powers. 

One of the most effective true thrillers in the series, "From Russia With Love" boasts a sense of taut suspense seldom equaled in the franchise. It's also the rare sequel that outdoes the original — upping the stakes, cranking up the drama, and delivering twists and turns that would make Sherlock Holmes blush. Connery cemented himself as the greatest spy in cinema, while the pre-title sequence and the use of advanced techno-gadgets marked the beginning of two long-running Bond traditions. 

2. Goldfinger

Easily the best film in the Connery-era James Bond film series, "Goldfinger" was the third entry in three years. Filled with every element of the tried-and-true Bond formula, the threequel has Bond bedding women, Q introducing fanciful gadgets, and a fiendish foe dead set on global domination — complete with a deadly henchman in the form of ruthless assassin Odd Job. 

In the film, the international menace known as Goldfinger concocts an elaborate scheme to rob Fort Knox and plunge the global economy into chaos. Only 007 can stop him, but when he's captured by the dastardly villain, it'll take all the tricks he has up his sleeve to save the world.

"Goldfinger" is Connery and Bond at their best. It's the perfect mix of mystery and intrigue, high octane thrills, dramatic plot twists, and explosive set pieces. The inclusion of Honor Blackman as the quintessential Bond Girl and the iconic theme song by Shirley Bassey made "Goldfinger" an instant classic.

1. The Man Who Would Be King

Written and helmed by legendary director John Huston, "The Man Who Would Be King" was based on a Rudyard Kipling novella first published in 1888. The film's famously languished in development hell for years, with the films cast evolving from Humphrey Bogart and Clark Gable to Sean Connery and Michael Caine. But once it landed, audiences were treated to one of the most epic adventures ever put to screen.

In the film, Connery and Caine play a pair of ex-British soldiers, Daniel Dravot and Peachy Carnahan respectively, who dream of discovering a primitive far-off land that they can conquer and rule. Through a series of good fortunes and serendipity, they find their lost world: an undiscovered country called Kafiristan. Pretending to be a holy man and his servant, the two are soon revered, with Dravot worshiped as a god while Carnahan condescends in frustration. Ultimately, "The Man Who Would Be King" is not the gripping thrills of James Bond nor does it explore complex issues or intrigue with unconventional ideas. It is simply a fun, light-hearted adventure with Connery as a would-be leader of men.