Ocean's Eleven (2001)

Ex-con Danny Ocean is out to even the score with Las Vegas casino owner Terry Benedict, who's now dating his, Ocean's, ex-wife Tess. The goal is straightforward: rob three casino resorts all sharing the same underground money vault, on fight night when the coffers will be stuffed. This is no simple smash-n-grab, however: Ocean and his buddy Rusty, bankrolled by a rival casino magnate, put together an offbeat team of experts -- pickpockets, explosives and surveillance geniuses, model builders, acrobats -- each assigned a specific task in the overall scheme. Casinos being somewhat protective of their on-hand cash, there are arcane, ridiculously elaborate security measures which must be overcome or disabled without alerting Benedict and his army of watchful goons that criminals are right beneath their impeccably mannered noses. Decadently stylish, sexy, and fun, just like Vegas itself -- and the team of diverse actors (including but in no way limited to Matt Damon, Don Cheadle, Elliott Gould, Bernie Mac) is having so much obvious fun, what George Clooney said about the Rat Pack-stocked original is equally true here: "You'd pay money just to watch those guys sit around and drink coffee." So what if the caper ultimately hinges on a couple of unlikely events and improbably timed coincidences? Or does it... The reveal at the end, laying out how the team tricked not only Benedict but also the audience into believing their "multiple cons" are anything other than smoke and mirrors designed to fool the casino goons into doing all the heavy lifting, is classic sleight of hand, if not downright slick dealing from the bottom of the deck. (Extra points for hilarious Trojan Horse usage of those ubiquitous escort brochures and "lady card" handouts that plague pedestrians along the Strip.) Still, this movie leaves burning questions: Does Clooney ever look disheveled, even when he's disheveled? Why is Brad Pitt so hungry? What is the ongoing appeal of Julia Roberts? The world may never know. Followed by imaginatively titled sequels Ocean's Twelve and Ocean's Thirteen.