- All-Star Cast: Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, Angie Dickinson, Joey Bishop, Richard Conte, Henry Silva, Norman Fell, Cesar Romero, Akim Tamiroff, George Raft, Red Skelton, Shirley MacLaine…
- Creator Backlash: In the Sinatra biography All the Way, Lewis Milestone said, "Ask me which was my least favorite film that I ever made and it has to be Ocean's Eleven".
- Harpo Does Something Funny:
- Significant portions of the movie interactions between major characters were ad-libbed. The actors playing the leading roles all knew each other well and improvised dialogue as well as or better than the script.
- Shirley MacLaine's cameo was ad-libbed.
- Scully Box: Sammy Davis Jr. required wooden blocks attached to the pedals on the garbage truck he drove in the film so that he could reach them.
- Throw It In!: In a scene between Danny and Adele, Adele throws a dish of candy at Danny. The throwing of the dish was ad-libbed, which accounts for the genuine look of surprise on Frank Sinatra's face and the faces of his co-stars.
- Uncredited Role:
- Shirley MacLaine has an unbilled cameo as a Tipsy Woman. She shot it during a break while filming Billy Wilder's The Apartment.
- Speaking of Billy Wilder, in the interview book Conversations with Wilder he claims he helped work on this movie's script without credit as a favor to Frank Sinatra. As a thank you, Sinatra gave Wilder a sketch by Pablo Picasso.
- Longtime Sinatra bodyguard and fight trainer-to-the-stars, Al Silvani, makes an uncredited cameo as the manager of the burlesque nightclub where Buddy Lester works.
- Vacation, Dear Boy: Shirley MacLaine agreed to a cameo as an excuse to hang out with her Rat Pack friends and see their Vegas show.
- What Could Have Been:
- The film's original ending had the crew escaping Las Vegas with the money by getting away on a chartered plane, but then the entire gang is killed in a plane crash. No one liked that ending as they felt it was too much of a downer, so it was rewritten.
- Steve McQueen (actor) turned down a role on the advice of his friend Hedda Hopper, who told him to be his own man rather than Frank Sinatra's "flunky".
- Peter Lawford was first told of the basic story of the film by director Gilbert Kay, who heard the idea from a gas station attendant. Lawford eventually bought the rights in 1958, imagining William Holden in the lead.
- Tony Curtis was originally offered a cameo role.
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