Ocean's Eleven (1960)

One of the coolest movies ever made, this all-star home movie was the first film to star the Rat Pack, Frank Sinatra’s posse who spent more time drinking, singing, carousing, and playing golf than they did acting. The thin story is credited to four writers, including science fiction legend George Clayton Johnson (TWILIGHT ZONE) and KISS OF DEATH’s Charles Lederer, and was directed by Lewis Milestone, who won two Oscars during Hollywood’s Golden Age.

OCEAN’S ELEVEN is a caper flick about a plan to rob five Las Vegas casinos simultaneously on New Year’s Eve. Danny Ocean (Sinatra) recruits ten members of his World War II paratroop unit to pull the caper, including just-in-from-Hawaii singer Sam Harmon (Dean Martin), garbage man Josh Howard (Sammy Davis Jr.), and wealthy mama’s boy Jimmy Foster (Peter Lawford). Pace is not this movie’s greatest asset, and its first hour is basically just Ocean getting the whole gang together.

Danny is visited by his estranged wife (Angie Dickinson), who is cool to the idea of their reconciliation. Foster is dismayed by his mother’s impending sixth marriage to hood Duke Santos (Cesar Romero). Tony Bergdorf (Richard Conte), upon learning he’s got “the Big Casino,” needs the loot from the caper to make sure his son is provided for after his death. Meanwhile, Martin and Davis sing, Sinatra and Lawford get messages, everyone wears V-neck sweaters, and characters stand around a lot just drinking Scotch and smoking cigarettes patiently while waiting for their next line.

No question about it—OCEAN’S ELEVEN is as empty as Dino’s liquor cabinet on New Year’s Day, but it’s hard not to be seduced by the insouciant charms of the stars. After performing onstage in the evenings and partying ‘til the wee hours of the morning, the Pack wasn’t in the mood for much complexity in their film, so Milestone basically stands them in front of the set, points his camera in their direction, and gets it all in one—heck, maybe occasionally two—takes. Much of the dialogue seems gleaned from their nightclub act.

Strangely, the film doesn’t feel as freewheeling as other vanity shows—like, say, CANNONBALL RUN, which is loose and sloppy between car stunts and face-slappings. In contrast, OCEAN’S ELEVEN emits a laidback quality — fitting, considering its stars — but its technical proficiency works against it. A film this bright, colorful, and well-staged ought to have more to its core than boozy indifference.

However, OCEAN’S ELEVEN is difficult to dislike. The stars are almost always fun, especially when they’re screwing around together, and look at who’s backing them up: Joey Bishop, Shirley MacLaine, Red Skelton, George Raft, Norman Fell, Akim Tamiroff, Buddy Lester, Joan Staley, Pinky Lee, Hoot Gibson, even Henry Silva. The songs, like Davis’ “E-O-Eleven,” by Sammy Cahn and Jimmy Van Heusen are catchy, and Dean’s “Ain’t That A Kick in the Head” is a jaunty classic (Steven Soderbergh, who directed the 2001 remake, used it in his ultracool crime flick OUT OF SIGHT). It all closes on a surprisingly downbeat twist, which, combined with a clever final shot, manages to leave you with a weightier taste than the movie probably earns. Ring-a-ding-ding.