I haven't seen the original Ocean's Eleven (blasphemy, I know), but I know I like this one quite a bit, even though it's not the type of movie I would normally gravitate toward. Before we get to the trivia, we'll do a quick cast recap:
Danny Ocean - George Clooney
Rusty Ryan - Brad Pitt
Frank Catton - Bernie Mac
Reuben Tishkoff - Elliott Gould
Virgil Malloy - Casey Affleck
Turk Malloy - Scott Caan
Livingston Dell - Eddie Jemison
Yen - Shaobo Qin
Saul Bloom - Carl Reiner
Linus Caldwell - Matt
Damon Basher Tarr - Don Cheadle
Tess Ocean - Julia Roberts
The casinos all gave the cast and crew more or less free reign of when and where they could shoot in the casinos. The exception, of course, were the money vaults and any behind-the-scenes corridors and things like that. Those were shot on a soundstage. It was a particularly big deal that Caesar's Palace allowed them to film a scene depicting a robber being shot directly in front of their place (during the flashback scenes of previous Vegas heists at the beginning). Steven Soderbergh credited this entirely to Jerry Weintraub's Vegas connections.
Carl Reiner accepted his role just five days before the first scene with his character was scheduled to be shot. Alan Arkin was supposed to play Saul but had to drop out at the last minute.
The entire poker game with the up-and-coming stars at the beginning of the film was pretty much ad-libbed. The stars, by the way, were Topher Grace from That '70s Show, Holly Marie Combs from Charmed, Joshua Jackson from Dawson's Creek, Shane West from Once and Again and Barry Watson from 7th Heaven. They've all done other movies and shows since, obviously, but these were their big hits at the time.
Brad Pitt is wearing a very large ring shown prominently in the scene where Rusty cons the young stars. He later mentioned that it was given to him by his wife and making sure it was caught on camera was his little to wink to her. At the time, his wife was Jennifer Aniston.
Matt Damon was such an adept pickpocket that the part near the beginning where he steals the wallet from a man on the el actually had to be slowed down so viewers could catch what he was doing.
Shaobo had never acted before. He didn't speak much English but was very adept at understanding when his lines were and had a natural knack for timing (according to Steven Soderbergh).
In the scene where Tess first comes down the stairs at the Bellagio while Linus and Rusty discuss her, you'll notice Brad Pitt is eating shrimp cocktail. Actually, he's eating something in nearly every scene he's in, which I'll get to in a second. It was Brad who decided that Rusty should be eating shrimp cocktail, and Steven Soderbergh warned him that the scene might have to be shot several times. Brad had no problem with that and ended up consuming about 40 shrimp.
Rusty Ryan is always eating because, basically, Brad Pitt thought it would be funny and appropriate - since these guys are always on the go in the movie, he thought that they would probably be eating on the go as well. It became a running joke to pick out and incorporate food for each of his scenes.
The directors, set designers and writers all purposely stayed away from obvious Rat Pack and Sinatra references. They wanted the movie to stand on its own and didn't want to make the characters complete cliches.
The movie's whole premise - that casinos have to keep enough money in their vaults to cover every chip currently in play on the floor - is a lie. In reality, casinos try very hard to keep the amount of extra cash in their vaults down to a minimum.
It's commonly believed that Ben Affleck has a little cameo somewhere in the movie - after all, his best friend and brother were two of the Eleven. Although he did come to set, he is never actually in the movie. Director Steven Soderbergh and Producer Jerry Weintraub have cameos, though. Soderbergh is part of the group that bombs the vault at the beginning and Weintraub talks with Saul before Saul goes to talk with Terry Benedict.
The cast all liked to gamble when they had some time off from shooting. Brad Pitt and Matt Damon both reported that Clooney was the worst, largely just due to luck - he never had decent cards. Don Cheadle said he tried to steer clear of the gambling entirely.
This tidbit is lifted directly from TV Guide, but it's too interesting to not include: When Rusty runs through the list of scams the group is going to have to pull, the names he gives them aren't just random.
The quote: "Off the top of my head, I'd say you're looking at a Boeski, a Jim Brown, a Miss Daisy, two Jethros and a Leon Spinks, not to mention the biggest Ella Fitzgerald ever." And the explanation from Steven Soderbergh:
"First of all, [screenwriter] Ted Griffin and I completely made the terms up. We felt we had to come up with some funny, Damon Runyon-esque turns of phrase that weren't arbitrary we did sit down and think them out. So, Carl Reiner is the Boesky, as in Ivan, the powerful, rich magnate, inside kind of guy. Jim Brown is the confrontation Bernie Mac has with Matt Damon the 'don't mess with me or you're in for it' moment. The two Jethros are Casey Affleck and Scott Caan, the idea being 'we're going to need gear heads, car fanatics...some people who are total hillbilly under-the-hood guys.' A Leon Spinks is the disruption of the boxing match: A sporting event with some controversy to it that's what Leon Spinks means to me. The Miss Daisy association is driving; that was the SWAT van, a ruse involving transportation. The Ella Fitzgerald is the tape of the fake vault, which they're going to play back and have [Andy Garcia's character] Benedict think it's live. 'Is it live, or is it Memorex?'"
There are at least a couple of points in the movie where Steven Soderbergh didn't want to meticulously arrange 11 actors, so he gave them the freedom to go where they wanted within the shot and do what they thought their characters would do. The first is when Danny Ocean is explaining the whole scam to them - Soderbergh told the actors to just position themselves wherever they wanted to in the room. The second is at the end when they are all standing in front of the Bellagio reveling in their accomplishment. He told them all to wander away from the fountain as they felt it was appropriate and gave them no timeframe or order to work with.
Ocean's lost three actors to The Royal Tenenbaums. Danny Glover was supposed to play Bernie Mac's part but dropped out to be in the Wes Anderson movie; Luke and Owen Wilson were going to play the Scott Caan and Casey Affleck parts until they ditched for the same reason.
Warren Beatty, Ralph Fiennes and Michael Douglas were all considered for the part of Terry Benedict. Ewan McGregor was considered for Basher, Don Cheadle's character. Mark Wahlberg was originally supposed to play Linus, Matt Damon's role.
When Brad Pitt plays the doctor that come to the rescue of 'Lymon Zerga,' he's wearing a wig that Mike Myers used to rehearse for Austin Powers. Brad was so unrecognizable when he put the wig and the glasses on, he wandered around the casino for a good 20 minutes just enjoying his anonymity.
Julia Roberts only spent two weeks on set. Speaking of Julia, watch for her name in the credits. Her credit reads, "And introducing Julia Roberts as Tess."
Don Cheadle was originally not listed in the credits. When asked why, he said that some things went down on the set behind the scenes that he didn't like, so he told the producers to just take his name off. But it must not have been too bad - he appeared in both Ocean's Twelve and Ocean's Thirteen.