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7 Best And 7 Worst Clint Eastwood Movies

Any "Mount Rushmore of Movie Stars" must include Clint Eastwood's iconic squint, though no stone could possibly do his granite jawline justice. Born May 31, 1930, Eastwood has been a movie star longer than most people's parents have been alive. Heck, he's been famous since before some people's grandparents were alive! Eastwood started working as an actor in 1954, landing bit parts in B-movies like "Tarantula" and "Revenge of the Creature" before his breakout role as Rowdy Yates in TV's "Rawhide" in 1959. Eastwood wanted to branch out to the big screen, but he was handcuffed by Hollywood's mistaken belief that nobody would buy a ticket to see an actor they could watch for free on TV. Bad call, Hollywood.

So Eastwood went to Italy, playing the Man with No Name in "spaghetti Westerns" for director Sergio Leone. Eastwood has been a movie star ever since. His career box office is $2.4 billion worldwide, which is even more impressive given his biggest hits were pre-multiplex. His starring role in 2018's "The Mule" opened to $17 million and made $173 million worldwide — at 88 years old! There are stars one-third his age who couldn't manage that. Eastwood makes it look easy. What isn't easy is knowing where to begin when reviewing his acting career, but we're here to help ("Do you feel lucky?"). With Rotten Tomatoes as our guide, here are the seven best and seven worst Clint Eastwood movies!

Worst: Dirty Harry's finale, The Dead Pool, underwhelmed

Before you get too excited, no, the Man with No Name never played the Merc with A Mouth. So Ryan Reynolds, your "Deadpool" legacy is safe (give or take "X-Men Origins: Wolverine"). Released in 1988, "The Dead Pool" is the fifth and final "Dirty Harry" movie ... or at least the last one with Clint Eastwood, since a reboot starring an unworthy, pencil-necked pretender seems inevitable. Eastwood plays his most famous character, Harry Callahan, the one-liner spewing, .44 Magnum-shooting, San Francisco police detective who never met a perp he didn't want to pummel. 

The perp in "The Dead Pool" is a serial killer who's taking out celebrities (including a punk rocker played by Jim Carrey in one of his first roles) on a "dead pool" put together by a horror director played by Liam Neeson. It's up to Dirty Harry to make the punk pay ... and make his day (oh wait, that was from "Sudden Impact"). As for why it ranks so low, it's largely because "The Dead Pool" is just an unoriginal thriller that pales in comparison to earlier films in the franchise. Anyway, despite being one of Eastwood's worst, it's not that bad, but the Tomatometer has spoken with a 55% from critics and 44% from audiences.

Best: Critics sung praises for Honkytonk Man

Clint Eastwood made himself a legendary movie star (and a multi-millionaire) playing cowboys, detectives, and more recently, grumpy old men who take no lip. But one of his most interesting roles was Red Stovall, a Depression-era, wannabe country music singer dying of tuberculosis in 1982's "Honkytonk Man," which Eastwood also directed. This is Eastwood's second most famous singing role (probably his second singing role ever) after 1969's "Paint Your Wagon," which would've made the worst list with its 27% critic's score, but audiences saved it with a 68% rating. 

While audiences were slightly less into "Honkytonk Man" (64% audience score on Rotten Tomatoes), critics liked it much more (93% score). We're with the critics. While "Honkytonk Man" clearly wishes it was "Paper Moon," it's still a sweet "grown-up and kid on the road" movie that manages to make you smile, not gag. Joining Eastwood in the film is his son, Kyle, playing Red Stovall's nephew. While it's fun watching Eastwood play against type, not many people saw it, as "Honkytonk Man" bombed with $3.6 million. Fortunately, Eastwood was back one year later in "Sudden Impact," the fourth movie in the "Dirty Harry" franchise.

Worst: Blood Work didn't work

Paint-by-numbers serial killer dramas were all the rage well into the 2000s. In fact, we're pretty sure Ashley Judd starred in a movie called "Paint by Numbers." Sadly, Eastwood got in on the game too, resulting in a movie that's solid enough for the genre but one of his worst. 

Eastwood directs and stars in 2002's "Blood Work," playing Terry "Don't Call Me Dirty Harry" McCaleb, a former FBI profiler who seems suspiciously like Dirty Harry. McCaleb suffered a heart attack while hunting "the Code Killer." When McCaleb discovers his new heart came from one of the killer's victims, McCaleb reopens the unsolved case. You'll probably be able to figure out who the killer is before the opening credits are over, though given the demands of the genre, it takes McCabe the film's nearly two-hour runtime. It's pretty routine, but if your routine is "watch a Clint Eastwood movie on TNT on a Thursday," it's fine. However, with a 52% critics' score and 40% audience score on Rotten Tomatoes, any viewer expecting a classic is bound to have a change of heart.

Best: This Western is one of Eastwood's greatest films

Clint Eastwood shocked the movie business when his 1971 directorial debut, "Play Misty For Me," turned out really good, with an 84% critic's score and 72% audience score. In 1973, Eastwood was back in the director's chair — and back in the saddle — for his second film and his first of many Westerns as a director, "High Plains Drifter." Eastwood again plays a man with no name, the Stranger, who wanders into a town where the locals are terrorized by bandits. 

Amazed by his gunslinging, the townspeople hire the Stranger to take out the bad guys. Hey, who needs seven samurai when you can get one Clint Eastwood? But there's more to this movie than the simple premise suggests, and by the time the end credits roll, you'll nod your head at the big reveal once you realize what "High Plains Drifter" had hidden up its sleeve all along. With a 93% critics' score and an 86% audience score on Rotten Tomatoes, "High Plains Drifter" isn't just one of Eastwood's best Westerns — it's one of his best movies, period.

Worst: This 'Eastwood meets Bond' movie should've been better

When it comes to "Firefox," we're happy to say Clint Eastwood didn't make a movie about the web browser of the same name, though mindlessly surfing the web is a better use of your time. Here, the titular Firefox isn't a search engine but a state-of-the-art Soviet fighter plane, which veteran American pilot Eastwood has been assigned to find. It's okay, but if "Firefox" was supposed to be "Clint Eastwood in a James Bond movie," then it should've been a lot more entertaining. 

Eastwood also directs, so he should be thankful he cast a movie star (himself) in the lead role, as his direction is slow and ponderous when it should be, well, James Bond-ian. Less "Hunt For Red October," more "For Your Eyes Only". Had Eastwood cast a less charismatic movie star than himself, "Firefox" would've put moviegoers to sleep. Eastwood's star power in these sorts of roles was enough to propel "Firefox" to $45 million worldwide, making a slight profit on a $21 million budget. This fighter jet dodged a bullet, but with a 38% critics' score and 42% audience score on Rotten Tomatoes, "Firefox" didn't fly far.

Best: In the Line of Fire proved Eastwood still had star power

Clint Eastwood was riding high after taking home Academy Awards for Best Picture and Best Director for "Unforgiven." Rather than retire (or heck, take a vacation), Eastwood took it easy (for him) and only acted in his next role, "In the Line of Fire." The film tells the story of a guilt-ridden Secret Service agent trying to protect the president, and Wolfgang Petersen, the German director behind such divergent titles as "Das Boot" and "The NeverEnding Story," sat in the director's chair. It turned out pretty well, as "In the Line of Fire" was one of the biggest hits and best movies of either man's career. 

Despite opening less than a month after "Jurassic Park," "In the Line of Fire" scratched an itch with Eastwood's fanbase of "grown-ups who like action movies," opening to $15 million and legging it out to $102 million domestically and $187 million worldwide. In other words, it was Eastwood's biggest hit adjusted for inflation at that point. There's a reason for this -– "In the Line of Fire" is really good, getting a 96% critics' score and 79% audience score on Rotten Tomatoes. While "Unforgiven" cemented Eastwood's status as an artist, "In the Line of Fire" proved he still had it as a movie star.

Worst: This movie was a rookie mistake

"The Rookie" follows the time-honored tradition of an established star (Eastwood) passing the torch to the up-and-comer (Charlie Sheen). It didn't work. At all. Eastwood directs the film and plays an aging police detective, and Sheen plays the titular rookie. The mismatched pair have to put aside their differences to take on a car-theft ring led by Raul Julia. When your movie's villain is played by Raul Julia and it's still unwatchable, you know it's bad. 

The biggest problem (of many) with "The Rookie" is that Eastwood and Sheen have zero chemistry. The rookie role would've been better served by someone like Tom Cruise or Mel Gibson, two actors who didn't need the rub at that point. "The Rookie" bombed, earning just $21 million in 1990, while over on Rotten Tomatoes, its 29% critic's score and 36% audience score is the worst of Eastwood's directorial career. Given he followed up "The Rookie" two years later with "Unforgiven," we'd say things worked out okay.

Best: Escape from Alcatraz is one of the best breakout movies

We'll just come out and say it — there aren't enough Alcatraz movies. The genre is so rock solid (pun 100% intended) that not even Michael Bay could screw it up. When you pair the genre with Clint Eastwood and Don Siegel, the director and star of numerous action hits, including "Dirty Harry," you get the genre classic "Escape from Alcatraz." As the title implies, "Escape from Alcatraz" is the true story of Frank Morris (Eastwood), an experienced prison escape artist who plots a breakout from the "inescapable" island prison outside of San Francisco. 

We can debate the morality of casting Clint Eastwood as the "hero" when he's playing a real-life, hardened criminal, but besides all that, "Escape from Alcatraz" is just a really good movie. Pardon the cliche, but it's the kind of "thriller for grown-ups" they don't make anymore. "Escape from Alcatraz" was a hit, earning $43 million in 1979, about $156 million today. And it's one of Eastwood's best movies, with a 96% critics' score and 85% audience on Rotten Tomatoes. There's no escaping this fact — "Escape from Alcatraz" is awesome.

Worst: City Heat was just sad

Sylvester Stallone and Arnold Schwarzenegger starred in "Escape Plan" decades past their heyday, and "City Heat" was a similar situation. It starred the two biggest stars of the 1970s, Clint Eastwood and Burt Reynolds, who by 1984 seemed to be past their primes. Sadly, that turned out to be true for Burt Reynolds, though Clint Eastwood reinvented himself in the early '90s. Pairing Eastwood with Burt Reynolds seemed like a sure thing, but "City Heat" was too little, too late, and way too awful. 

The film, in which Eastwood and Reynolds are both miscast as Humphrey Bogart-like 1930s gumshoes, made a so-so $38 million – pretty mediocre considering it starred two guys who could've beaten that number on their own just a few years before. The fact it's terrible didn't help, with 22% from critics' and 24% from audiences over on Rotten Tomatoes. In another universe, there's a blockbuster '70s movie where Eastwood plays a humorless detective and Burt Reynolds a smart aleck criminal. In this universe, we have to suffer through "City Heat."

Best: Unforgiven is an Eastwood masterpiece

The revisionist Western is a sub-genre itself. In fact, do they even make old-school Westerns anymore? Not after "Unforgiven," the best and most celebrated revisionist Western of them all, which was directed by one of the genre's best directors and featured one of its biggest stars. Both are the same man — Clint Eastwood. 

"Unforgiven" is the tale of a reformed killer who, desperate for cash, takes one last job and crosses paths with a violent sheriff (Gene Hackman). It's also one of the rare instances of a director commenting both on the genre that made him famous and his own screen persona. Kinda like if Sylvester Stallone made a boxing movie about a pugilist that wasn't "Rocky." While much ink has been spilled about the meaning of "Unforgiven" in the three decades since its release, we imagine the notoriously unpretentious Eastwood just figured he was a filmmaker lucky enough to land a great script. 

"Unforgiven" made Eastwood a two-time Oscar winner, taking home Best Director and Best Picture in 1993. Unlike many Best Picture winners, its reputation has only grown with age. "Unforgiven" is an absolute masterpiece, and the Tomatometer backs us up. The film boasts a 96% from critics and 93% from audiences, a rare across-the-board crowd pleaser and his best movie as a director.

Worst: Pink Cadillac crashes and burns

The 1980s was a big decade for American movies ... but not so much for Clint Eastwood. Eastwood's movies still made money, especially when he was Dirty Harry or co-starring with an orangutan, but the future four-time Oscar winner was in a creative rut. And despite being the biggest movie star of the '70s, he was now trailing new stars like Harrison Ford, Tom Cruise, Mel Gibson, Sylvester Stallone, and Arnold Schwarzenegger. Eastwood closed the 1980s with one of his biggest creative and commercial misfires, "Pink Cadillac." 

The tone deaf, unfunny comedy about a bounty hunter chasing an attractive bail jumper was swallowed by the triple whammy of "Indiana Jones and the Last Crusade," "Ghostbusters II," and "Batman" when it was released in May 1989, earning $12 million total, less than those blockbusters made in two days. Solid counter-programming can survive and even thrive in the face of a blockbuster, but "Pink Cadillac" crashed and burned, with a 21% critics' score and 24% audience score on Rotten Tomatoes. Eastwood started the 1990s with two more bombs ("White Hunter, Black Heart" and "The Rookie") before reasserting his star power with "Unforgiven."

Best: A Fistful of Dollars made Eastwood a star

Clint Eastwood was an up-and-coming TV star when he took a flight to Italy and made a movie that changed his life — and cinema — forever. The film was "A Fistful of Dollars." The director was Sergio Leone. The story was Akira Kurosawa's "Yojimbo," which Leone and company never got permission to remake ... whoops. It didn't matter, as "A Fistful Of Dollars" was so awesome that it made Eastwood a star, and it's still one of his best movies ever, with a 98% score from critics and 91% from audiences on Rotten Tomatoes.

That's about on par with the 95% critics' score and 96% audience score for "Yojimbo," making it one of the best remake ever too, which may have something to do with the fact it's a shot-for-shot remake in places. While direction is important, not just any actor can don Toshiro Mifune's kimono. Okay, Eastwood didn't either — the Man With No Name wore a poncho — but still, only a movie star of Eastwood's magnitude could take this role and make it so iconic.

Worst: Eastwood's worst movie stinks worse than an ape

What was Eastwood's biggest box office hit, adjusted for inflation? Not "Million Dollar Baby," "Unforgiven," or "Dirty Harry" ...but "Every Which Way but Loose." Yes, the orangutan movie. With $104 million, $422 million adjusted for inflation, "Every Which Way but Loose" earned more in North America than any other Eastwood movie, even his biggest directorial hit, "American Sniper." But we're not here to talk about that orangutan movie — we're talking about its sequel, "Any Which Way You Can." 

With $70 million domestically, over $200 million adjusted, "Any Which Way You Can" was also one of Eastwood's biggest hits ... and also his worst ever movie according to Rotten Tomatoes, with 20% from critics and 45% from audiences. While the reviews are mostly bad, they're scattered, with Roger Ebert saying, "It's hard not to feel a grudging affection for it," while Nick Schager says it's maybe "Eastwood's most disposable movie." We'll take critic Rob Vaux's advice: "It's Eastwood. It's a monkey. It's a lot funnier if you're blind drunk." Hey, when a movie's this bad, you have to watch it any which way you can.

Best: The Good, the Bad and the Ugly is the best

Cue the iconic whistle. "The Good, the Bad and the Ugly" is Clint Eastwood's best movie. However, there's a caveat. While "A Fistful of Dollars" has a critics' score only 1% higher (98% versus 97%), its audience score is a bit lower (91% vs. 97%). So "The Good, the Bad and the Ugly" is an across-the-board favorite. Just to cement its spot atop our list we consulted IMDb, where it landed a 8.8/10 score compared to "A Fistful of Dollars" getting 8.0/10. So we feel good about putting about putting this particular spaghetti Western at number one. 

Though to be honest, both are must-watch movies, as is the second film in the "Dollars Trilogy" – "For A Few Dollars More" – which just barely missed the cut with a 92% critics' score and 94% audience score. What can we say? Eastwood has been in a lot of classics, which removes the stink of "The Rookie" and "Pink Cadillac" ... more or less. But when it comes to the top spot, there can be only one — "The Good, the Bad and the Ugly."