According to Frank Sinatra Jr. on the DVD Commentary, Sammy Davis Jr. was forced to stay at a "colored only" hotel during the filming because Las Vegas would not allow blacks to stay at the major hotels despite his appearing with Frank Sinatra, Dean Martin, and the others at the Sands Hotel. He was only allowed to stay at the major hotels after Frank Sinatra confronted the casino owners on his behalf, therefore breaking Vegas' unofficial color barrier.
In a scene between Danny (Frank Sinatra) and Adele (Patrice Wymore), 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 Sinatra's face and the faces of his co-stars.
Shirley MacLaine's tipsy uncredited cameo was ad-libbed by the actress, for which she reportedly received a brand new car from Warner Bros. as compensation. Her line, "I'm so drunk I don't think I could lie down without holding on," was a rehash of a classic Dean Martin line.
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.
Most filming was accomplished early in the morning, before sunrise, since most of the actors also had shows in Las Vegas that they performed nightly during the shooting. The actors would wake up in the afternoon, do one or two shows in the evening, then go through make-up and arrive at the shooting locations for principal photography. Each shooting location was fully set up in advance so that minimal time would be wasted once the actors arrived.
During Dean Martin's scene with Shirley MacLaine, after she calls him "Ricky Nelson", Martin replies "I used to be Ricky Nelson but now I'm Perry Como." In real life, early in his singing career, music critics used to derisively refer to Martin as a knock off of Perry Como. In addition, Martin had just done Rio Bravo (1959) co-starring Ricky Nelson.
KLAS TV reporting in the wake of the heist was a real Las Vegas media station. Not long after this movie was released, Vegas millionaire resident Howard Hughes bought it so he could control what movies aired on late night television.
According to Billy Wilder in the interview book "Conversations with Wilder" he helped work on the script as a favor to star Frank Sinatra. As a thank you, Sinatra gave Wilder a sketch by Pablo Picasso.
As Peter Lawford, Dean Martin and Frank Sinatra attempt to disguise themselves by blackening their faces in the garbage truck near the end of the movie, Sammy Davis Jr. says, "I knew this color would come in handy some day." Martin and Sinatra teased Davis about that scene for as long as they knew each other thereafter.
In the final shot of the film, the eleven walk past the famous sign in front of the Sands hotel. The five members of the Rat Pack (Frank Sinatra, Dean Martin, Sammy Davis Jr., Joey Bishop, and Peter Lawford) are billed on the sign. They were performing alternately in the hotel's Copa Room during production, at the "Summit at the Sands".
Shirley MacLaine shot her quick cameo during a break in filming The Apartment (1960). Although she was offered a car for her work, she says she took the job as an excuse to hang out with her Rat Pack friends and see their Vegas show.
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.
Right after the heist when Sheriff Wimmer is interrogating a possible witness over the phone, the uncredited voice on the other end of the line is that of George Fenneman, better known as the announcer on such TV game shows as You Bet Your Life (1950) and Tell It to Groucho (1962).
In the theatrical trailer, the announcer states "Danny Ocean is holding his own summit". This is a possible joke reference to the legendary Rat Pack shows at the Sands which took place during filming. The shows were known as "The Summit".
Sinatra was not the first to hear about this film. Peter Lawford was first told of the basic story of the film by director Gilbert Kay. Kay heard about it from a gas station who told him his ideas for the story. But when Sinatra first heard the idea. He said "Forget the movie. Let's pull the job".
Major Taylor, the head of the boys military academy, is based on Donald L. Nichols, head of the Palo Alto Military Academy. Nichols was known as 'The Major' from his service with the California National Guard.
As most of the cast were performing at nights in Las Vegas, it was an almighty struggle to schedule their filming appearances. Joey Bishop would always be at the 9am call start, Peter Lawford would only work in the mornings, Dean Martin and Sammy Davis Jr. would show up in the afternoon and Frank Sinatra would make his appearance at 5pm.
Prominent names of entertainment personalities, all well known to 1960 audiences, appear on the marquees of the various casinos: Gisele MacKenzie, Phil Foster, and Harry James at the Flamingo, Danny Thomas, Red Skelton (who also appears in a credited cameo), and Red Norvo at the Sands, Louis Prima and Keely Smith at the Desert Inn, Patrice Munsel and Buddy Hackett at the Riviera, and Donald O'Connor, Sidney Miller and Freddy Martin at the Sahara; only Red Norvo actually performs on screen, accompanying Dean Martin on stage.
At the time of filming, stage money, which did not look anything like the real thing, was still required, either because of the production code, or legal technicalities which had not yet been disentangled. Alfred Hitchcock's Psycho (1960) seems to be the breakthrough film, in which, stage money which actually looked authentic was prominently used, a big step forward for motion picture makers.
This was the second movie in two years co-starring Frank Sinatra and Dean Martin that ends with a recitation of the 23rd Psalm. The final scene of Some Came Running (1959) ends with a graveside funeral scene where the 23rd Psalm is recited.
The set of the grand staircase in Ilka Chase's home (used in the scene where Peter Lawford first meets Cesar Romero) had previously been seen as Rosalind Russell's posh Manhattan apartment in the 1958 version of Auntie Mame. In that film, the set was given several different "facelifts" as the film's plot followed Mame Dennis' adventures through several decades.
The set of the grand staircase in Ilka Chase's home (used in the scene where Peter Lawford first meets Cesar Romero) had previously been seen as Rosalind Russell's posh Manhattan apartment in the 1958 version of Auntie Mame. In that film, the set was given several different "facelifts" as the film's plot followed Mame Dennis' adventures through four decades.
Peter Lawford's story about going skiing at Squaw Valley could not actually happen due to the entire resort being under construction for the 1960 Winter Olympics which were held there in February, a month after the film was completed.
The trivia items below may give away important plot points.
According to Frank Sinatra Jr. in the DVD Commentary, Danny Ocean and his men made it out of Las Vegas with the money by getting away on a chartered plane (flown by one of the Eleven). 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 to the ending shown in the movie with the money being burned up along with Tony Bergdoff's body in cremation. The idea for the cremation ending came from director Lewis Milestone, who had recently attended the cremation funeral of a friend.
The entire Ocean's Eleven appear together only twice: around the pool table at Acebos' house and also at the bowling alley. Although it was noted above that all were in the final shot walking the Strip, this was after the funeral and Bergdorf was not included.
When the Sheriff's Office gets the phone call from The Flamingo reporting the robbery there is no description of the offenders or how they pulled it off yet within a minute another cop takes a phone call and announces 'They've just hit the Sands too'.