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30 Greatest Frank Sinatra Movies Ranked Worst To Best

While Frank Sinatra is primarily recognized for his music, he appeared in dozens of films over the course of his career. Although you may think of the musicals initially, there was so much more to him as an actor. Of course, he was perfectly suited to musicals, but he also shone in a number of dramatic and comedic roles during his time in Hollywood. He had a reputation for hating rehearsals, but he routinely brought the goods when the cameras rolled, becoming a banker at the box office.

Not all of the films he appeared in were good, but some of them were truly great. The movies listed below are the pick of the bunch, ordered from worst to best. The order was determined not only by the plot and cultural impact of these films, but also by the part Sinatra played in them. So, what are Frank Sinatra's all-time greatest movies? Read on to find out.

30. The Pride and the Passion

1957's "The Pride and the Passion" is a flawed but nonetheless interesting movie. Although the story is complicated, it features some great talents of the time — Frank Sinatra stars alongside Cary Grant and Sophia Loren. It is set during the Napoleonic Wars and features a British captain named Trumbull (Grant), who goes to Spain. He is there to keep the French from getting their hands on a huge cannon. When he arrives, he discovers that the Spanish HQ has been taken over by a guerrilla group. Miguel, played by Sinatra, is the leader of that group.

Given the star power of Sinatra, Grant, and Loren, this movie should have been a big hit. Sinatra felt awkward in his role, and things were made even more complicated by Grant's romantic pursuit of Loren. Even with these things, this film is worth a look. "The Pride and the Passion" is far from perfect, but it shows another side of these actors.

29. Young at Heart

A musical remake of the successful film "Four Daughters" from 1938, 1954's "Young at Heart" follows the Tuttle family as a man named Alex (Gig Young) enters their lives and all three daughters fall for him. When his musical arranger Barney (Sinatra) shows up, one of the daughters, played by Doris Day, sees him as a challenge and falls in love with him while trying to change his cynical outlook.

With Day and Sinatra together, you have some great songs and a heartwarming storyline. The musical pulls out a happy ending, which will leave you with a smile on your face. This was Sinatra's first film following his successful return in "From Here to Eternity." He's a few years into his difficult marriage with Ava Gardner, and it shows on his face. He looks beaten down, but still manages to belt out some amazing tunes and convey a character whose life is turned around by love.

28. Not as a Stranger

The 1955 film noir "Not as a Stranger" is based on a novel by Morton Thompson and is primarily a vehicle for Robert Mitchum, who plays an aspiring doctor. Lucas is a medical student who can't afford to pay for medical school, so he marries nurse Kristina (Olivia de Havilland) and uses her for her money. He is so focused on his medical work that he pretty much ignores his wife, his mentor, and his best friend Alfred, played by Frank Sinatra. Not only is he a jerk to all of them, but he also cheats on his wife with wealthy widow Harriet, played by Gloria Grahame.

Sinatra has a relatively small part here, but he's great to watch whenever he's on the screen and takes part in one of the film's most emotional scenes. One cool thing about "Not as a Stranger" is that it was one of the first films to show a real human heart beating. Mitchum and Olivia de Havilland reportedly attended eight real life surgeries to prepare for their roles, adding another layer of authenticity.

27. Kings Go Forth

1958's "Kings Go Forth" is about a WWII love triangle. Sam, played by Frank Sinatra (who narrates the film), and Britt, played by Tony Curtis, both fall in love with Natalie Wood's character. Set against the backdrop of the end of the war in Europe, the men encounter Monique, an American woman living in France. She chooses one, breaking the heart of the other, and reveals there is more to her than meets the eye.

This film is a callback to some of Sinatra's earlier works in which he has trouble with women. The role of Monique was originally conceived with Dorothy Dandridge (the first African American nominated for a best actress Oscar) in mind. Even though Sinatra is older than both Natalie Wood and even Leora Dana (who plays her mother), he still manages to convince you that he may be a good fit for her, injecting youthful vigor into his performance.

26. Never So Few

In 1959, Frank Sinatra appeared in another WWII film. Set in the dense jungles of Burma (now known as Myanmar), "Never So Few" is based on a true story. The film features Sinatra in the lead role of Captain Tom Reynolds, who helps train the Kachin natives in jungle combat as Japanese troops close in. Meanwhile, he becomes involved in a love affair with a woman named Carla (Gina Lollobrigida), the wife of a wealthy merchant.

Sammy Davis Jr. was set to star alongside his Rat Pack buddy in this one, but the two friends had fallen out, so Sinatra had him replaced with Steve McQueen. Davis Jr. made the mistake of saying during a radio interview that he was a better singer than Sinatra. "The loss of the role was heartbreaking, as was the loss of the $75,000 salary," biographer Gary Fishgall said. "To be seen as a cruel ingrate by the man he esteemed above all others was almost more than he could bear."

25. The Joker Is Wild

"The Joker Is Wild" is a film that you should definitely see at least once if you're a Frank Sinatra fan, but it's a difficult watch. This faithful biopic features Sinatra as comedian Joe E. Lewis, who started out as a promising singer. This gave Sinatra plenty of opportunities to show off his voice with tunes like "All the Way," "Swingin on a Star," and "I Cried for You." When Lewis leaves the speakeasy he's singing at, the mobster who owns it has some of his lackeys cut Lewis' throat, severing his vocal cords and leaving him for dead.

Sinatra portrays the devastation of this character so well that your heart breaks for him. He is also at his best with his own vocals, and learning about Lewis is an intriguing ride. Sinatra and Lewis were friends in real life and the Rat Pack man later signed him to his record label.

24. The Kissing Bandit

1948's "The Kissing Bandit" stars Frank Sinatra as Ricardo, a young man who couldn't be further from his father's legacy. His dad was not only a skilled thief, but one kiss from him would send the ladies swooning. His father's old gang wants him to follow in his footsteps, but Ricardo could not be more awkward. He falls in love with the governor's daughter (Kathryn Grayson), who believes him to be the original Bandit and the only girl he didn't kiss.

Although the premise is outdated, "The Kissing Bandit" is an enjoyable musical that makes the most of Sinatra and Grayson's chemistry. The pair had previously appeared together in "Anchors Aweigh" and "It Happened in Brooklyn." Despite this movie's reputation for being goofy and a little cheesy, it contains a number of memorable tunes and some unforgettable dance sequences, making it a must-see for any Sinatra fan.

23. Some Came Running

Dean Martin and Frank Sinatra's first big screen collaboration, "Some Came Running" is a melodrama made even more interesting by the addition of Shirley MacLaine. It follows veteran Dave (Sinatra) as he returns to his small hometown in Indiana. Unfortunately, he is now an alcoholic and resentful. Dave falls in love with Gwen (MacLaine), but a girl named Ginnie follows him from Chicago and causes trouble for everyone. When Gwen is slow to return his affections, Dave discusses his problems with Bama, played by Martin.

This movie helped cement the friendship of Martin, Sinatra, and MacLaine, turning the latter into an honorary Rat Pack member. Although Sinatra clashed with director Vincent Minnelli, reportedly walking off set more than once, the final product was a great film that critics still love to this day. "Sinatra's performance is one of his most quietly impressive, and Martin and MacLaine are equally great," said Decider. "Their work, combined with the movie's impeccable cinematic sense, make 'Some Came Running' soar."

22. The Detective

The 1968 crime thriller "The Detective" is one of Frank Sinatra's grittiest films. He plays Detective Joe Leland, who gets tasked with investigating the murder of a gay man. In the process of his investigation, the dead man's roommate confesses to the killing, but something seems amiss. Joe soon uncovers corruption within the police force and aims to expose the cover-up job. If you get burned out on his musicals, this role is an impressive departure for Sinatra. There was a ton of drama behind the scenes on this one, too.

"The Detective" led to Sinatra's divorce from Mia Farrow, who was supposed to star with him. She was busy making "Rosemary's Baby" and refused his offer. He was so upset that he replaced her and served her divorce papers on her movie set. They remained close in the years that followed, however. "He came back, over and over and over and over," Farrow told Vanity Fair. "I mean, we never really split up."

21. None But the Brave

The only feature film that Frank Sinatra directed, 1965's "None But the Brave" follows a group of American soldiers who get stranded on an island in the Pacific after a plane crash during WWII. They soon discover that a group of Japanese troops have also been stranded on the island, and an uneasy truce between the two groups is called. Sinatra plays chief pharmacist Mate, who performs surgery on a Japanese soldier in one memorable scene.

Sinatra almost got more than he bargained for filming in Hawaii, because he nearly drowned. He got caught in a current while out for a swim and lost consciousness fighting against the waves. He had to be rescued by actor Brad Dexter, who played Sergeant Bleeker. "I stretched Frank out in the sand and gave him artificial respiration," Dexter told biographer Kitty Kelley. "Once he started vomiting water out of his lungs, I handed him over to lifeguards." The grateful star made Dexter vice president of Sinatra Enterprises soon afterward.

20. The House I Live In

This short is a departure from the rest of the films discussed here, but it is still an important work of Frank Sinatra's and belongs on this list. It is about 10 minutes long and features a significant lesson. Filmed in 1945, it stars Sinatra as himself. He's in the middle of a recording session when he decides to take a quick smoke break. In the alley behind the studio, he encounters a group of kids chasing another boy.

The boys tell him that they are after him because he is of a religion different from their own. Sinatra proceeds to school them on tolerance, telling them that his father came from Italy but that doesn't make him any less American. The short ends with Sinatra singing the titular song as the enlightened kids watch on in awe. This film is available on YouTube and is one that Sinatra fans should see if they haven't already.

19. Come Blow Your Horn

1963's "Come Blow Your Horn" is another of Sinatra's films where he plays a ladies' man who doesn't want to give up the lifestyle. He stars as Alan, an eternal bachelor who decides to show his younger brother what life as a single man in Manhattan can be like. This doesn't go down well with their father, who wants his boys to join the family business. Alan eventually recognizes that it's time to grow up, but he takes little brother Buddy on an adventure first.

This Oscar-nominated film (based on the Neil Simon stage comedy of the same name) might be a little dated at this point, but it is "carried forward at a jaunty pace and in high spirits," veteran Cleveland Press film critic Tony Mastroianni wrote. "Frank Sinatra is well cast as the bachelor rogue, and if he seems to be playing himself most of the time that's all right — the part is conceived in the Sinatra image."

18. 4 for Texas

Zack, played by Frank Sinatra, and Joe, played by Dean Martin, are rival businessmen traveling to Texas in the same stagecoach. They work together to protect a shipment of $100,000 from an outlaw band headed up by Matson, played by Charles Bronson. Once they arrive at their destination, they continue their rivalry by bidding on the same waterfront casino. The two men decide to unite in an uneasy partnership. "4 For Texas" also features their new girlfriends, played by Anita Ekberg and Ursula Andress.

While Sinatra and director Robert Aldrich reportedly didn't get along, any collaboration between Martin and Sinatra is always fun to watch, since the two were such great friends in real life and this comes across on screen. They have amazing chemistry, and you can tell how much they enjoyed working together. It is important to note that this is the only movie they did together where they weren't friends within the film.

17. Higher and Higher

1943's "Higher and Higher" focuses on the staff of businessman Mr. Drake (Leon Errol). When they learn that he is broke, they set out to help him. His valet (Jack Haley) comes up with a scheme to pass scullery maid Millie (Michele Morgan) off as Drake's daughter in an effort for her to snag a rich husband. Problems arise from the fact that she's in love with Frank Sinatra's character (named, believe it or not, Frank Sinatra), who lives across the street.

One of Sinatra's earliest works on this list, "Higher and Higher" is lighthearted and fun. It was his first real acting role, but it was assumed that he had no skill except to play himself, which he proved wrong as he used it to launch his acting career. Sinatra "does a nice job even though he's asked to do little but handle a few lines of dialogue and sing five of the film's eight songs," said film critic Dennis Schwartz.

16. Suddenly

In a departure from his usual roles, Frank Sinatra plays a villainous assassin named John Baron in the 1954 film "Suddenly." He is out to murder the president in this dark noir. He takes over the home of Ellen Benson, played by Nancy Gates, which looks ideal for his ambush. Ellen and her family are held at gunpoint as John waits for the opportune moment. The storyline pulls you in from start to finish, with the suspense levels high.

This role shows another side of Sinatra's range as an actor. While he is a villain, he is still captivating. He plays the psychotic killer well, disturbingly self-assured as the family he has taken hostage attempts to plead with him. It has long been rumored that Lee Harvey Oswald watched "Suddenly" before assassinating Sinatra's good friend President John F. Kennedy, leading Sinatra to demand the film be pulled from circulation. This has never been proven, however.

15. From Here to Eternity

"From Here to Eternity" is a classic that takes place in 1941 at a U.S. Army base located in Hawaii. It follows the story of Prew, played by Montgomery Clift, whose captain hears of his boxing skills. Prew tells him he doesn't do that anymore, so the captain has others mess with him. Sinatra plays a friend of Prew, who has troubles of his own in the shape of Fatso Judson, played by Ernest Borgnine. It features other big names, such as Burt Lancaster, Deborah Kerr, and Donna Reed.

Sinatra's billing here was low as he was coming off a career nosedive following an incident in which he hemorrhaged vocal cords. His wife at the time, Ava Gardner, allegedly helped him get the part of Maggio, which earned him an Oscar and saved his career. If you are a Sinatra fan, this one is an absolute must-see.

14. Double Dynamite

For a great movie with Groucho Marx separated from his brothers, check out his collaboration with Frank Sinatra in 1951's "Double Dynamite." Sinatra stars as Johnny, a broke bank teller who wants to put together some cash so he can marry his girlfriend. He comes into some reward money when he stops a bookie from getting beaten up. Unfortunately, it is the same amount as a shortage from the bank where Johnny works. He must prove his innocence with the help of his friend Emile, played by Marx.

A highlight of the film is Sinatra and Marx performing the song "It's Only Money" together. Although Sinatra was reduced to third billing, he is the protagonist of the movie and the one you root for the entire time. It's a silly comedy, "but a fairly diverting one," critic Bob Thomas wrote in the San Bernardino Sun-Telegram. "The geniality of the performers keeps this one from becoming a dud."

13. It Happened in Brooklyn

1947's "It Happened in Brooklyn" follows Frank Sinatra's Danny, who is recently out of the army and happy to be returning home to Brooklyn. He soon discovers a much less friendly place than when he left. Danny meets a teacher named Anne, played by Kathryn Grayson, and runs into the janitor of his old school, played by Jimmy Durante. He falls for Anne as he works on helping one of her students get a music scholarship.

This film was the first pairing of Peter Lawford and Sinatra. Lawford plays a friend of Danny who also falls in love with Anne, creating a love triangle. This movie is one of the three in which Lawford sang. It also contains a funny scene of Sinatra and Durante singing "The Song's Gotta Come From The Heart," where Sinatra imitates Durante's style with an impressive gravelly voice that you don't usually hear from him.

12. Anchors Aweigh

"Anchors Aweigh" was the first pairing of Frank Sinatra and Gene Kelly. The film was Sinatra's first solid step into moving past singing cameo roles. He plays Clarence, who, along with Kelly's character Joe, earns a three-day leave from the Navy. They soon run into a woman with movie star aspirations, played by Kathryn Grayson. Clarence decides he wants a girl to come home to, but Joe develops feelings for the same girl, which sets up a complication for the two.

As was common before his Oscar win, Sinatra plays a character who is super shy and knows nothing about women, while Kelly plays the expert on the ladies. The dynamic works, and the baby-faced Sinatra — though close to 30 at the time — is endearing. His ballads are romantic, and you find yourself rooting for him to find love and gain some confidence. Sinatra hasn't fully come into his own as a dancer yet because he watches Kelly's feet during their numbers together (this is especially evident in the "I Begged Her" number), but it doesn't make the movie any less enjoyable.

11. Can-Can

"Can-Can" is one of Frank Sinatra's lesser-known films, but it's also one of his most enjoyable to watch, particularly if you're into period pieces set in Paris. It features great performances by Shirley MacLaine, Maurice Chevalier, and Louis Jourdan. The story follows Simone (MacLaine), a nightclub owner who has her performers dance the can-can, which is illegal in 1890s Paris. She soon runs into trouble with a judge (Jourdan), who falls in love with her even though she's dating François Durnais, a lawyer played by Frank Sinatra.

The interesting thing about this Sinatra film is that his character wasn't even in the original play. His production company was behind the film, so he was pretty much able to do whatever he wanted. A close musical colleague of Sinatra's, Nelson Riddle, was the musical director of the film, which features stellar songs by Cole Porter. The story is entertaining, and the songs are top-notch. "The best tune from the original, as sung by Sinatra, is still 'C'est Magnifique,'" said Variety.

10. The Tender Trap

His first playboy role and the beginning of the shift in his film persona, 1955's "The Tender Trap" stars Frank Sinatra as Charlie, a theater agent who has his pick of the ladies. When his friend Joe comes to visit, he is staggered by the number of women that Charlie is dating. His whole philosophy is thrown to the wind when he meets Julie (Debbie Reynolds), who has the tender trap all set. She is seeking a husband, and although he is initially looking for fun, Charlie dates her anyway.

Despite his caddish behavior, Sinatra manages to create an endearing character in Charlie as the film progresses. He and Reynolds became good friends while filming, as she revealed during an interview with The Telegraph. "I loved to party with the Rat Pack, they were so much fun," she said. "All they did was have a good time. We'd get off work at two in the morning and hang out at a club and listen to other performers. I loved Frank Sinatra. If he liked you it was forever, and if he disliked you — I wouldn't want to be there."

9. Pal Joey

1957's "Pal Joey" follows Joey Evans as he gets in and out of trouble with dames. When he lands a job as a nightclub singer, he soon gets distracted by all the girls around him. Of particular interest is Linda English (Kim Novak), who resists his charms for much of the movie. As he falls in love with Linda, he hooks up with an older woman (Rita Hayworth), who buys him his own nightclub. Things get complicated when he realizes he can't get over Linda.

"Pal Joey" is based on the play that starred Gene Kelly in the title role. One of the biggest changes was that Sinatra tailored the character to fit him more closely rather than sticking with how Joey was in the play. His signature look is strong here with his suit and fedora. The songs are catchy and one of them, "The Lady is a Tramp," would become a favorite of Sinatra's set.

8. Robin and the 7 Hoods

1964's "Robin and the 7 Hoods," an innovative take on the story of Robin Hood, features Frank Sinatra alongside his Rat Pack buddies Sammy Davis Jr. and Dean Martin. Sinatra stars as Robbo, a Chicago gangster with a good heart. He enters into a gang war with Guy Gisborne (Peter Falk) over who should take over after mob boss Big Jim gets taken out. They try to one-up each other over the course of the film while Big Jim's daughter plays them against each other.

The combination of Martin, Sinatra, and Bing Crosby (who plays Allen A. Dale, a version of Alan-a-Dale from the Robin Hood legend) is magical as they sing together in the song "Style." The film was originally supposed to include a kidnapping scene, but Sinatra had it scrapped after his son was kidnapped during the making of the movie. The kidnappers demanded $240,000 for Frank Jr.'s release. The ransom was paid and he was set free five days after he was marched from a hotel room at gunpoint.

7. The Manchurian Candidate

"The Manchurian Candidate" is another intriguing non-musical from Frank Sinatra. He stars as Major Bennett Marco, who fought in the Korean War and is plagued with nightmares as a result. He dreams that two of his men were killed by his sergeant, Raymond Shaw. The nightmares are so disturbing that he visits Shaw, where he encounters Shaw's Communist mother, fantastically played by Angela Lansbury. Marco soon discovers that he isn't the only one having nightmares.

The mystery behind what really happened in Korea is the focal point of this film. It keeps you guessing as you seek to unravel the truth along with Marco. Sinatra turns in a powerful performance, and you find that you care about his well-being as he unmasks the true villain of this story. He was so committed to his role that he broke one of his fingers during a fight scene. It reportedly caused him pain for the rest of his life.

6. Guys and Dolls

Adapted from the hit musical of the same name, 1955's "Guys and Dolls" features Frank Sinatra as Nathan Detroit, who is trying to fund his floating crap game. He makes a wager with high roller Sky Masterson that he can't take missionary Sarah Brown to Havana with him. Meanwhile, Nathan's fiancée Adelaide wants him to give up the crap game and marry her instead.

Although the song "Luck Be A Lady" became a popular tune for Sinatra later on, he was not the one to sing it in the "Guys and Dolls" movie. Much to his chagrin, Marlon Brando got the part of Sky and that song. Even though he was disappointed in his role, Sinatra still shines and plays the part of Nathan Detroit with charm and humor. He never got along with Brando during filming, but, thankfully, that doesn't translate to the screen.

5. Take Me Out to the Ball Game

Frank Sinatra reunited with Gene Kelly in the summer-centric film "Take Me Out to the Ball Game." Dennis (Sinatra) and Eddie (Kelly) are two baseball players who dabble in vaudeville during the offseason. When they return to the game, they find out that their team has been sold and that the new owner is going to be actively participating in the management. When K.C. Higgins (Esther Williams) shows up, they are all flabbergasted that she's a woman. Eddie tries to woo her while being distracted by a gambler who engages him in a show to tire him out so the team will lose.

There are some major differences between this 1949 film and "Anchors Aweigh," released four years earlier. The biggest is that you can see how Sinatra's confidence has changed in his dancing. While he watches Kelly's feet for guidance in "Anchors Aweigh," here, he doesn't even glance over, looking every bit the multi-talented star.

4. On the Town

The 1949 musical "On the Town" has a premise similar to "Anchors Aweigh," except that instead of two sailors on leave, there are three. They added Jules Munshin to the Gene Kelly and Frank Sinatra duo here. The three sailors embark on a one-day leave in New York City, where one wants to sightsee, another wants to find a girl he saw on a poster, and the third is just along for the ride. The sailors find love and adventure on their one day off.

Sinatra and Kelly's last collaboration, "On the Town" features great music, a fun story, and film advancements — this was the first big budget musical shot on location in the Big Apple. Producers had to keep it as low profile as possible due to Sinatra's popularity at the time. "It was apparently too difficult for then-teen-idol Sinatra to perform in the middle of the real Times Square without causing a riot," the New York Post reported.

3. Ocean's 11

"Ocean's 11" is the ultimate heist movie, and the 1960 version is leagues above the 2001 remake in execution, talent, and story. It follows Frank Sinatra's Danny Ocean as he rallies his pals to pull off an impressive Las Vegas heist across five casinos on New Year's Eve. Despite his stellar voice, Sinatra does not sing at all in this one. Even though it's not really a musical, it does feature songs by both Dean Martin and Sammy Davis Jr.

As one of the best Rat Pack films, "Ocean's 11" features a stellar cast that combines Sinatra, Martin, Davis Jr., Peter Lawford, and Joey Bishop. These men were the core of the Rat Pack, and it's clear when watching the film that they were having a lot of fun together. The storyline is clever, and the dynamic of everyone in the cast reels you in and holds your attention as you wonder if they will get away with their audacious plan.

2. The Man with the Golden Arm

Director Otto Preminger's film "The Man with the Golden Arm" was a groundbreaking story about a former drug addict who just got out of prison and is determined to make a better life for himself. Unfortunately, falling back into bad habits proves too hard to avoid as he must support his wheelchair-user wife while in love with another woman. The film is based on the novel by Nelson Algren and also stars Kim Novak and Eleanor Parker.

Due to the subject matter, the Motion Picture Association of America initially refused to approve the film, though the success of the picture forced a rethink. The following year, the production code was changed to allow films that included drug addiction. Sinatra's role in "The Man with the Golden Arm" showed that he was way more than just a singer. The scene where his character goes through withdrawal is painful to watch, and he is brilliant in his depiction of a struggling heroin user. While not as magical as many of his musical roles, this 1955 film is highly rewatchable and helps you develop a deeper appreciation for who Sinatra was as an actor.

1. High Society

1956's "High Society" stars Frank Sinatra as reporter Mike Connor, who has been permitted to cover the upcoming wedding of Tracy Lord (Grace Kelly). The tabloid that Connor works for has obtained some embarrassing information about Tracy's father, and his bosses use this as leverage to gain access to the highly-anticipated nuptials. To further complicate matters, Tracy's ex-husband (Bing Crosby), who is still in love with her, shows up just in time to take in the chaos and stir old feelings. When she falls for Sinatra's reporter, Tracy is forced to choose between the three suitors.

Many things make this Sinatra's best movie. From the music to the acting to his co-stars, this one is a real must-see. The film shows off his singing and his acting, but also his comedic talents. It was also monumental because it was Grace Kelly's final feature film before she retired to marry the Prince of Monaco. The leads all have great chemistry — Sinatra and Kelly have palpable sexual tension, especially during the amazing ballads "Mind if I Make Love to You" and "You're Sensational." His scenes with Bing Crosby are also a lot of fun, particularly their duet "Well, Did You Evah!" This film is an exhibition of Sinatra's talents and is still as entertaining today as it was back then.