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4 Great Movies With Frank Sinatra

Updated on September 9, 2014
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You've Either Got or You Haven't Got...

Style. Class. A voice fit perfectly for jazz and the natural know-how of acting, Frank Sinatra had it all and wasn't afraid to let everybody know it. In the late 1930's his career began as a singer on radio programs and as 1940 rolled in he was number one in popularity among the country's bobby-soxers. While an eardrum disorder caused him to be unfit for military service during World War II, he toured with the USO and by the mid-1940's he was co-starring in movie musicals like Anchors Aweigh (1945) and On the Town (1949). Sinatra took on a role in From Here To Eternity (1953) and won an Academy Award for Best Supporting Actor. From this point his appeal changed from teen audiences to adults. Creating a tough guy reinvention of himself, he dipped into television with little success. In the 1960's he aligned himself with Dean Martin, Sammy Davis Jr., and others to form The Rat Pack. They set up base in Las Vegas singing and performing at clubs and casinos and were a hit right away. This is the lasting impression remembered most by our current culture of Frank Sinatra and our fascination has only increased with time-- which is why you should check out these four relatively forgotten films starring Frank Sinatra.

The Tender Trap (1955)

An adaptation of a stage play by Max Shulman and Robert Paul Smith, The Tender Trap (1955) tells the story of a lifelong bachelor named Charlie Reader (Frank Sinatra) and his assorted affairs. One girl for Monday, two on a Wednesday-- He's booked all week. How does he get them all? He's a talent agent for the theatre and has plenty to choose from. When his old pal Joe comes to visit citing a boring marriage and need for excitement it seems that Charlie is happy to continue in this wild lifestyle. That is until one poignant audition where he meets Julie, played by Debbie Reynolds. She has life all figured out-- career, marriage, children and by what age these will become a reality. Charlie chases Julie for his little black book , and in true romantic comedy fashion she strikes him down at his every attempt for tenderness. It's a heartfelt film with the additional charms of Celeste Holm, as a special 'Girl Friday' to Charlie, providing a calming aid to the madness that is The Tender Trap.


The clip below features Frank schooling Debbie Reynolds on how to properly perform the title song "The Tender Trap".

The Tender Trap song clip

High Society (1956)

There is general acceptance that those in a meaningful status can spare room for frivolity and scandal in their lives, it's no different for the Lord family in High Society (1956). This film takes the plot of The Philadelphia Story (1940), adds a number of swinging jazz tunes and replaces Grant, Hepburn and Stewart with Crosby, Kelly, and Sinatra. That's Grace Kelly, she plays Tracy Lord, a woman about to be married for the second time (with the first ending with social gossip); Bing Crosby takes the role of her ex-husband, Dexter Haven, who unexpectedly shows up to her wedding weekend extravaganza; and Frank Sinatra is the man sent to cover the spectacle for SPY Magazine, a purveyor of celebrity lives. Add in the musical styling's of Louis Armstrong, and again the assistance of Celeste Holm, ultimately utter mayhem ensues in High Society.


Watch some of the chaos as Frank and Bing Crosby share a bonding song in the clip below.

High Society "Did you, Evah?" clip

Ocean's 11 (1960)

Ocean's 11 (1960) is an original film in what is so far a list of remakes and adaptations, and was ironically remade in 2001 starring George Clooney and Brad Pitt. This 1960 version stars the five men of The Rat Pack and features five of the original Vegas Strip casinos. Sinatra, along with Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop are part of a gang of WWII vets set on planning the heist of a lifetime. Marking the Sands, Sahara, Flamingo, Riviera, and Wilbur Clark's Desert Inn as the targets, they plan to wipe each house out in one night. The film oozes "cool" and has a style not seen in today's film industry. Consisting of a classic cast, memorable cameos, and an outstanding musical number by Sammy Davis Jr. (which you can watch below), Ocean's 11 (1960) is a heist film that will leave you wanting more from The Rat Pack.

Ocean's 11 "Ee-O-Eleven" clip

The Rat Pack
The Rat Pack | Source

Who are The Rat Pack?

The Rat Pack in it's original form was a group of Hollywood stars from the classic age of film, made famous by their lavish parties. Headed by Humphrey Bogart, they were fully known as the Holmby Hills Rat Pack, named after the home Bogart shared with his wife, Lauren Bacall, in which many parties occurred. After Bogart's death in 1957, Frank Sinatra, took control and The Rat Pack became what is now remembered as a boozy, talented group of entertainers who performed on the stages of Vegas casinos for many years, consisting of Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop.

Robin and the 7 Hoods (1964)

By far one of the greatest guilty pleasures of all-time, Robin and the 7 Hoods (1964) takes the tale of Robin Hood, brings it into 1930's Chicago, and makes it a musical. Sinatra stars as Robbo, a Chicago gangster struck by the sudden murder of "Big" Jim, who ran the main joint ring of the town. "Big" Jim's daughter Marion returns for the funeral and gives Robbo $50,000 to kill whoever murdered her father. Robbo declines, but Marion pays him anyways. In an attempt to get rid of the money it is mistakenly donated to a local boys' home. Robbo and his merry gang of gun wielders are now heralded as "Do-gooders" of the town. With added pressure from a rival gang led by Guy Gisborne (Peter Falk) and a crooked Sheriff, trying their best to keep him out of business, Robbo keeps up the "steals from the rich and gives to the poor" idiom while successfully running an underground gambling joint. The film has plenty of entertaining musical numbers, and fun throwback references to the original Robin Hood tale, including Dean Martin as Little John, Sammy Davis Jr. as Will, and Bing Crosby as Allen A. Dale.

In the clip below we watch as Robbo hides his business and puts up a front as a church group for alcoholics. The singing starts 3 minutes in.

Robin and the 7 Hoods "Mr. Booze" Scene

Poll Time!

Split decision: Frank Sinatra or Dean Martin?

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Looks like you've all go some watching to do!

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    • Kelsey Thaves profile image
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      Kelsey Thaves 3 years ago from Twin Cities

      Well, that is because it's the truth! :)

    • goodmovies profile image

      Randy Ray 3 years ago from Texas

      I used to tell my girlfriend that Frank Sinatra invented "cool".