Dean Martin's "Ain't That a Kick in the Head" remains synonymous with Ocean's 11, the all-star casino heist film responsible for cementing the legend of the Rat Pack – the gaggle of crooners, movie stars and sycophants whose inimitable style and swagger defined postwar cool.
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Composer Jimmy Van Heusen and lyricist Sammy Cahn wrote "Ain't That a Kick in the Head" expressly for Ocean's 11, filmed on location on the Las Vegas Strip in early 1960. Frank Sinatra, the Oscar-winning matinee idol around whom the Rat Pack orbited, starred as ringleader Danny Ocean and produced the movie through his own Dorchester Productions, offering supporting roles to pals like song and dance man supreme Sammy Davis Jr., standup comedian Joey Bishop and actor Peter Lawford, the brother-in-law of then-presidential hopeful John F. Kennedy. Martin, who rose to stratospheric fame in nightclubs and Hollywood comedies opposite comic Jerry Lewis, previously co-starred opposite Sinatra in the 1958 drama Some Came Running, but he was ambivalent about his place in the Rat Pack hierarchy.
"[Martin] liked Sinatra, but knew him for what he was: A half-mozzarella that never grew up," Nick Tosches writes in his masterful 1992 biography Dino. "Bishop, Davis and Lawford were nobodies. They needed Sinatra, he did not… If people wanted to call him part of [the Rat Pack], so be it, fuck it; it made no difference."
From Jan. 26 through Feb. 16, Martin, Sinatra, Davis, Bishop and Lawford filmed Ocean's 11 each day and held court onstage at the Sands Hotel and Casino each evening; every hotel room in Vegas was booked throughout the duration of the shoot, with even JFK detouring from the campaign trail to make the scene. "Most mornings, they would come offstage at half past one or a quarter to two, drink till dawn, and begin filming," Tosches notes.
Martin recorded "Ain't That a Kick in the Head" with conductor Nelson Riddle on May 10, 1960, a day after completing the soundtrack album to the musical comedy Bells Are Ringing, in which he starred alongside Judy Holliday. He also performs an alternate arrangement of the song onscreen, supported by vibraphonist Red Norvo and his quartet. Capitol Records released "Ain't That a Kick in the Head" as a single in July 1960, about a month ahead of Ocean's 11's premiere; despite its boozy, bawdy charms, the record failed to chart, but it has grown to be recognized as one of Martin's signature songs thanks to its association with the film, widely considered the quintessential Rat Pack outing.
"It wasn't that it wasn't professional," Ocean's 11 co-star Angie Dickinson told Tosches about the production. "But you'd have to look hard to find a camera to prove to you that they weren't playing. They really had fun together."
