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Top 10 Frank Sinatra Films

Lindsay is a working actress and honors graduate of Texas Christian University with a Bachelor of Fine Arts degree in Theatre: Film/TV.

Who Was Frank Sinatra?

Frank Sinatra has been called “The Voice,” “The Chairman of the Board,” and “Ol’ Blue Eyes.” A master of song-styling with an iconic voice, Sinatra remains one of the best-selling musical artists of all time and one of the most popular singers of the 20th century.

Sinatra is often associated with his talented group of friends: Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop. Together they became immortalized as the Rat Pack (a term inherited from Humphrey Bogart’s old friend group) when they started performing now-legendary shows together in Las Vegas. Highly influential, Sinatra’s musical legacy can not be overstated. He won 11 Grammys throughout a recording career that predates the award by over a decade.

Indeed, with his phenomenal singing career inevitably taking precedence, it’s easy to forget that Frank was also one of Hollywood’s greatest stars. Whether playing a shy choir boy or a career criminal, Sinatra’s onscreen presence is undeniable.

An Oscar-winning actor in his own right, Frank was just as likely to appear in a gritty drama as he was a musical comedy, and you’ll find both represented on this list. If you’ve never been introduced to Frank Sinatra’s filmography, now may be the time to take your first look into the film career of this legendary star.

A Note on This List's Order

I chose the order of my Frank Sinatra top 10 by considering each film’s importance in Frank’s overall career, the size/importance of his role in them, and their overall popularity today, as evidenced by their ratings on sites like IMDb and Rotten Tomatoes.

Naturally, feel free to watch them in any order you like (this is merely a recommended top 10). You might watch them in the order listed here, chronologically (like I did), or in a way that corresponds with your own movie tastes.

Top 10 Frank Sinatra Films

  1. Pal Joey
  2. The Manchurian Candidate
  3. The Man With the Golden Arm
  4. On the Town
  5. Anchors Aweigh
  6. Suddenly
  7. Von Ryan's Express
  8. High Society
  9. Ocean's Eleven
  10. Not as a Stranger

1. Pal Joey (1957)

Based on the Rodgers and Hart stage musical of the same name, Pal Joey is a movie that perfectly crystallizes all aspects of Frank Sinatra's iconic persona. The film centers around shameless womanizer Joey Evans (Frank), who has just arrived in San Francisco after being run out of Chicago for flirting with the wrong girl.

Joey quickly weasels his way into an MC job at a local nightclub, where he meets sweet chorus girl, Linda English (Kim Novak). Unlike the other girls at the club, Linda is too smart for Joey's usual games, which Joey finds both intriguing and mildly infuriating. But, his focus on Linda shifts when he meets former stripper and current high society widow Vera Simpson (Rita Hayworth). Joey knows that getting close to the wealthy Vera could help him reach his dream of running his own nightclub, so he sets his sights on winning her heart (and, by extension, her finances).

The part of Joey Evans is a perfect fit for Sinatra, making good use of his Rat Pack bravado and roguish charm. However, Frank's Joey is considerably more likable and redeemable than his Broadway counterpart. Plus, the stage version of Joey isn't even a singer but a dancer. In fact, the role was originated on Broadway by none other than Gene Kelly.

Originally, it had been intended for Kelly to reprise the role of Joey on film with Rita Hayworth as Linda to capitalize on the pairing's earlier success in Cover Girl. However, it took 15 years for the film to get made, and by that time, Kelly was no longer under contract at Columbia Pictures. Despite that, Hayworth remained attached to film, now in the more mature role of Vera.

Naturally, the highlight of Pal Joey is seeing Frank perform some of his classic standards, all of which he recorded specifically for the film. Along with songs from the original Broadway version, the film's soundtrack was supplemented by songs from some other Rodgers and Hart musicals, including the classic "The Lady is a Tramp" from the musical Babes in Arms.

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2. The Manchurian Candidate (1962)

This tense political thriller features what is often considered one of Frank’s greatest onscreen performances. Based on the novel by Richard Condon, the film stars Frank as Major Bennett Marco, an Army veteran of the Korean War who begins to suspect that his memories of a specific combat mission in Manchuria may not be entirely reliable.

After this mission, Staff Sergeant Raymond Shaw (Laurence Harvey) was given the Medal of Honor for his actions (at Marco’s recommendation). However, Marco’s been suffering from nightmares that he and his platoon were, in fact, brainwashed by communist spies with Raymond, in particular, conditioned as a sleeper agent. Although Army Intelligence dismisses Marco’s concerns at first, that all changes when another soldier from his platoon comes forward with the exact same recurring dream.

Directed by John Frankenheimer and adapted for the screen by acclaimed playwright George Axelrod, The Manchurian Candidate is an unnerving and frighteningly relevant film, both at the time of its release and today. The plot was so politically charged that the head of United Artists, Arthur Krim, was initially hesitant to green-light the film at all.

But, Sinatra was so excited to do the movie that he, actually, asked President John F. Kennedy to call Krim about the film, himself. In fact, JFK was a fan of the original book, so he assured Krim that the film had his blessing, and he was looking forward to seeing it once it was finished.

3. The Man With the Golden Arm (1955)

Based on the novel by Nelson Algren, The Man with the Golden Arm features Sinatra in what is, easily, one of the best performances of his entire career. Set in Chicago, the film tells the story of Frankie Machine (Frank), a former drug addict who has just returned home after getting clean at a rehab center.

Excited at the prospect of a fresh start, Frankie is ready to turn his life around and pursue a new career as a professional drummer. But, coming back home to his possessive wife and old friends threatens to drag Frankie right back into self-destructive habits and derail all of his plans for a better life.

His only hope may depend on the one person supporting his new dream: his neighbor, Molly (Kim Novak). Directed by Otto Preminger, The Man with the Golden Arm was one of the first Hollywood films to revolve around the controversial subject of drug addiction. Although Frankie Machine's drug of choice in the original novel is morphine, the drug is heavily implied to be heroin in the film version (despite the fact that it is never explicitly named).

Sinatra's performance in this film garnered a great deal of critical praise, including an Oscar nomination. To prepare for the role, Sinatra spent time at drug rehab clinics, observing addicts attempting to go "cold turkey". Due to the film's drug use, the movie did not initially receive the Production Code's seal of approval, but United Artists decided to release the film anyway.

Likewise, in a notable break from tradition, the influential Catholic Legion of Decency, actually, disagreed with the Code's ruling, merely giving the movie a B rating (meaning only "partly objectionable"), rather than the dreaded Condemned. Despite its lack of Code approval, many large theater chains refused to ban the film.

This chain of events actually led to the Production Code being revised, allowing future films to touch on similarly controversial or taboo subjects with more leniency. The Man with the Golden Arm was even given a belated Production Code seal of approval in 1961, which allowed it to be shown on television and reissued into theaters.

4. On the Town (1949)

Based on the popular Broadway musical (which is, itself, inspired by the ballet Fancy Free), On The Town ended up being the last in the series of buddy pictures Frank appeared in opposite Gene Kelly. The movie features a fantastic ensemble alongside Frank and Gene, including Betty Garrett, Ann Miller, and Vera-Ellen.

It tells the story of three Navy sailors on 24-hour shore leave in New York City. One of the sailors, Gabey (Kelly), sees a poster of the subway’s current “Miss Turnstiles”, Ivy Smith (Vera-Ellen), and becomes obsessed with meeting her. He enlists his friends, Ozzie and Chip (Frank), to help and they all separate to find Ivy before their time runs out. However, each of the boys manages to get distracted by their own romantic interests along the way.

Chip, in particular, catches the attention of their pretty cab driver, Hildy (Garrett), almost immediately. Without a doubt, On The Town is most famous for its opening number, “New York, New York”. The sequence was filmed in NYC at Gene Kelly’s insistence, making this the very first movie musical to ever be shot on location.

However, the biggest challenge the production faced during that location shoot was finding ways to avoid Sinatra’s legions of fans. Shot at the very height of Frank’s bobby-soxer popularity, various attempts to hide the camera had to be made in order to keep the shoot as low-profile as possible and, hopefully, attract less attention to Sinatra’s presence.

And, in case you were wondering, a low-key subway beauty contest like Miss Turnstiles did, in fact, exist in NYC at the time. Its real name was “Miss Subways” and lasted from 1941–1976. Subway car posters would feature ladies who lived and worked in NYC with winners either picked monthly or every other month (in reality, professional actresses, models, and other entertainers were ineligible to apply).

5. Anchors Aweigh (1945)

Although not his first acting role, the success of this fun musical was what finally launched Sinatra’s acting career. Anchors Aweigh tells the story of Clarence Doolittle (Frank) and Joe Brady (Gene Kelly), a couple of Navy soldiers who are given shore leave in Hollywood as a reward for earning Silver Stars in battle.

Clarence is a shy choir boy from Brooklyn and begs womanizer Joe to help him get a date. Even though Joe already has his own date with an old flame, he reluctantly agrees to help Clarence first. However, the boys’ cruising plans get waylaid when they get roped into accompanying a Navy-obsessed child named Donald (Dean Stockwell) back home. Forced to wait until Donald’s Aunt Susie (Kathryn Grayson) gets home, by the time she finally arrives, it ends up being too late to find a date for Clarence. But, that’s alright with Clarence, for he immediately develops a crush on Susie and begs Joe to help him win her affections.

Partially made as a morale booster for the US Navy, Anchors Aweigh is the first of three films Frank would, eventually, make alongside Gene Kelly. This movie, also, marks the first time Kelly ever choreographed a film entirely by himself. One of the film’s most famous sequences features Kelly dancing opposite Jerry Mouse (of Tom and Jerry fame) in a fantasy dream sequence.

Originally, the filmmakers had hoped to use Mickey Mouse in the sequence, but Walt Disney declined to loan out Mickey to another studio. So, the already MGM-owned Jerry Mouse was used instead. Due to Frank’s already established singing career, all of Sinatra’s songs in the film were written especially for him. The only exception is a brief performance of the classic “Brahm’s Lullaby”.

6. Suddenly (1954)

Based on a story from Blue Book magazine called Active Duty, Suddenly gave Frank the rare opportunity to play a true villain. Set in the small town of Suddenly, California, the film revolves around the town getting a rare dose of excitement when they’re given notice that the President’s train will be making a short stop-over at their depot.

For security purposes, very few people are made aware of the President’s planned stop and government agents are sent in to prepare for the President’s arrival. Meanwhile, former military sharpshooter John Baron (Frank) is making his own preparations. Baron now makes his living as an assassin for hire and his next planned target is the President of the United States.

Adapted for the screen by the story’s original author, Richard Sale, this simple little melodrama features a standout performance by Frank. His menacing performance as Baron is the real highlight of the film and among Sinatra’s best onscreen performances.

Although originally shot in black-and-white, the film has been colorized in recent years so, you’re likely to run across both versions on streaming and DVD. A common rumor has circulated that JFK assassin Lee Harvey Oswald watched this film shortly before committing his heinous crime. True or not, it is easy to draw comparisons between the Kennedy assassination and the one attempted in the film.

7. Von Ryan’s Express (1965)

Based on the novel by David Westheimer, this WWII adventure film proved to be one of the most financially successful films of Sinatra’s career. Frank stars as the titular Colonel Joseph Ryan, a WWII Air Force pilot who is shot down over Italy and taken to an Italian POW camp.

When Ryan arrives, he discovers that the primarily British prisoners have attempted to escape so many times that the Italian officer in charge has retaliated by withholding food, clean clothes, and other care packages, causing many of the men to fall ill. Knowing how close Italy is to surrender, Col.

Ryan thinks the escape attempts are doing far more harm than good and the small number of American prisoners agree. As the camp’s senior officer, Ryan takes command of the imprisoned soldiers but, his philosophy of canceling all plans of a prison break does not sit well with the senior British officer, Major Eric Fincham. And when Italy finally does surrender, their problems only grow. Now the POWs must, somehow, find their way to freedom while avoiding the German forces.

An immediate fan of the book, Sinatra had, originally, attempted to buy the film rights to Von Ryan’s Express, himself. So, when he heard that 20th Century Fox had snatched it up, he immediately threw his hat in the ring to play Col. Ryan. Frank had, also, hoped that Richard Burton would co-star with him, but 20th Century Fox wouldn’t consider casting Burton after the troubled production of Cleopatra (which had, also, starred Burton). If the jacket Frank wears throughout this film looks a bit familiar, you might be a Hogan’s Heroes fan. Frank’s jacket ended up being worn by Hogan’s Heroes star Bob Crane throughout the entirety of the classic sitcom’s run.

8. High Society (1956)

A musical adaptation of the 1940 movie The Philadelphia Story (which was, itself, based on the play by Philip Barry), High Society features an all-star cast with a musical score by legendary composer Cole Porter. Sinatra plays the role of tabloid reporter Macaulay “Mike” Connor. Mike and photographer Liz Imbrie (Celeste Holm) are sent to Newport, Rhode Island by their employer, Spy Magazine, to cover the upcoming nuptials of high-class socialite Tracy Lord (Grace Kelly) to the nouveau-riche George Kittredge.

Tracy is not happy with having reporters cover her wedding but, she is tolerating it in exchange for the magazine keeping salacious details about her father’s infidelity out of the public eye. Also muddying up Tracy’s wedding plans is the presence of her ex-husband, C.K. Dexter Haven (Bing Crosby), a professional musician in town for Newport’s yearly jazz festival. High Society memorably features the musical stylings of Louis Armstrong peppered throughout the film as well, playing himself as a guest of the jazz festival and acting as a narrator of sorts.

This fun jazz musical is, probably, most notable for being Grace Kelly’s last film before her retirement and marriage to Prince Rainier III of Monaco. Kelly’s real Cartier diamond engagement ring is, actually, visible in the film, acting as Tracy’s engagement ring. In adapting The Philadelphia Story into a musical, one major change was moving the setting from Philadelphia to Newport, Rhode Island. This was done, specifically, to take advantage of the real Newport Jazz Festival, which had only been established a couple of years earlier (the popular event continues to be held annually to this very day).

Naturally, a lot of publicity surrounded Sinatra and Crosby finally appearing in a film together. Bing’s involvement in the film was, actually, a big motivator for Frank to agree to do the movie in the first place. The song “Well, Did You Evah” (from the Cole Porter musical DuBarry Was A Lady) was added at the last minute to finally give the two iconic crooners the chance to sing a duet together.

9. Ocean’s Eleven (1960)

Considered by many to be the ultimate Rat Pack movie, this comedy heist film stars the entire Rat Pack five: Frank, Dean Martin, Sammy Davis, Jr., Joey Bishop, and Peter Lawford. Ocean’s Eleven even features a memorable cameo by the unofficial Rat Pack “mascot” Shirley MacLaine.

The film stars Frank as Danny Ocean, a WWII Army veteran who recruits ten friends from his old unit to pull off the biggest robbery Las Vegas has ever seen. The plan is to rob five of the biggest casinos in Vegas on New Year’s Eve, simultaneously. There is little room for error and the risk is high. Every element of the plan must work perfectly. If one thing goes wrong, everything could fall apart spectacularly for Danny and his friends.

Unfortunately, it’s almost inevitable that something will go wrong. Made while the Rat Pack was performing nightly in Vegas, Ocean’s Eleven was filmed in Las Vegas inside the actual hotels mentioned in the film (i.e. The Flamingo, The Sands, The Desert Inn, The Riviera, and The Sahara). Due to the accepted rules of unofficial segregation in place in Las Vegas at the time, Sammy Davis Jr. was, originally, placed in a separate “colored only” hotel rather than be allowed to stay with the rest of the cast at the hotels used for filming.

Sinatra put an end to this by confronting the casino owners, himself, finally forcing them to break their self-enforced segregation rules. Due to the close friendships of the cast, large portions of Ocean’s Eleven ended up being ad-libbed. This included Shirley MacLaine’s cameo, which was entirely unscripted. MacLaine later said that she only did the cameo as an excuse to hang out with her Rat Pack friends.

10. Not as a Stranger (1955)

Directed by Stanley Kramer in his directorial debut, this medical melodrama features Frank in a smaller role this time around. Based on the novel by Morton Thompson, Not As A Stranger stars Robert Mitchum as Lucas “Luke” Marsh, a highly ambitious and arrogant medical student so dedicated to becoming a great doctor that it almost borders on obsessive.

Unfortunately, his judgement of other doctors is equally unyielding, with no imperfection ever going unnoticed. Luke’s single-minded quest for perfection is starkly contrasted by his best friend and roommate, Alfred “Al” Boone (Frank). Al is naturally more happy-go-lucky and not prone to dwell on the more serious aspects of being a doctor. However, he is a genuinely compassionate person at heart.

Meanwhile, Luke’s perfect plans for his life are upended when his alcoholic father squanders his tuition money. Dropping out is not an option so, Luke starts wooing the wealthy Kristina “Kris” Hedvigson (Olivia de Havilland), a demure Swedish nurse. Luke isn’t particularly interested in Kris romantically but, marrying her would secure him financially so he can continue his studies. But, Luke’s obsessive focus on work, along with his unrelenting quest to be the “perfect” doctor is doomed to fail from the start and everyone can see it, except him.

Not As A Stranger features a fantastic supporting cast, including Lon Chaney, Jr., Gloria Grahame, Broderick Crawford, and Harry Morgan. Although not very well-known today, the film was actually United Artists’ highest grossing film at the time it was released. Both De Havilland and Mitchum sat in on multiple surgeries to prepare for the film’s extensive surgical scenes. Not As A Stranger is, actually, one of the first films to show an actual human heart during an open-heart surgical procedure.

Honorable Mention: From Here to Eternity (1953)

I couldn’t possibly finish a Frank Sinatra Top Ten without mentioning the film that revitalized Frank's career and won him an Oscar for Best Supporting Actor. Based on the novel by James Jones, From Here To Eternity revolves around the lives and loves of two Army soldiers stationed in Hawaii right before the bombing of Pearl Harbor.

The film features an all-star cast that, along with Frank, includes Burt Lancaster, Deborah Kerr, Montgomery Clift, Ernest Borgnine, and Donna Reed. Lancaster plays the role of Sgt. Milton Warden, who is having a passionate affair with the wife of his commanding officer. Clift plays Pvt. Robert E. Lee Prewitt, who is being bullied into joining the unit’s boxing team against his wishes.

Sinatra plays the role of Pvt. Angelo Maggio, Prewitt’s likable but, loudmouthed, friend who finds himself in the crosshairs of the base’s sadistic stockade warden, Sgt. “Fatso” Judson (Borgnine). Frank’s role as Maggio is relatively small but, incredibly impactful and memorable. Although legend has it that Sinatra got the role of Maggio through his Mafia connections (a rumor that provided the basis for a memorable subplot in The Godfather), in reality, that legend has been debunked by various members of the film’s cast and crew.

In fact, multiple people have credited Frank’s wife, Ava Gardner, as being the one most responsible for helping Frank the part. During the making of the film, Frank became quite close with co-star Montgomery Clift. The Method-trained Clift even helped coach Frank through many of his scenes.

Unfortunately, the two did not remain close as time went on, when Clift’s substance addictions became more severe. However, Sinatra did retain lifelong friendships with both Burt Lancaster and Ernest Borgnine. Frank and Borgnine, actually, made a tradition of sending each other yearly Christmas cards, always signing them as “Fatso” and “Maggio”.

Learn More...

If you would like to learn more about Ol’ Blue Eyes, check out the books, Frank: The Voice (2011) and Sinatra: The Chairman (2015) by James Kaplan. I would, also, highly recommend watching the fantastic 2015 documentary, Sinatra: All Or Nothing At All.

© 2020 Lindsay Blenkarn


Umesh Chandra Bhatt from Kharghar, Navi Mumbai, India on August 22, 2020:

Nice compilation. Well done.

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