“Say we get into the cage and through the security doors and down the elevator we can’t move and past the guards with the guns and into the vault we can’t open,” posits Carl Reiner’s character Saul Bloom in the 2001 heist movie Ocean’s Eleven. “Say we do all that, we’re just supposed to walk out of there with 150 million dollars in cash on us without getting stopped?”

Cut to Danny Ocean, a.k.a. George Clooney: “Yeah.”

Okay, that’s pretty much all it takes for 10 disparate con men to follow Clooney/Ocean into the robbery of three Las Vegas casinos  – and for audiences to buy in as well. 

Ocean’s Eleven – which also starred Brad Pitt, Matt Damon, Andy Garcia, Elliott Gould, Bernie Mac, Don Cheadle, Casey Affleck, Scott Caan, Eddie Jemison, Shaobo Qin and – according to the title credits, “Introducing Julia Roberts” – is celebrating its 25th anniversary with a rerelease in theatres this month (starting June 20). The film, which was a remake of a 1960 movie starring The Rat Pack, made a pop-culture and box-office impact in 2001 with its playful, self-aware, wry and a little self-deprecating edge (see the Roberts joke above). It was a vibe tailored to these particular stars, and had a whole different tone than the usual heist movie – thanks to auteur supreme Steven Soderbergh. The year before he had made two films, Erin Brockovich and Traffic, that both earned Oscar nominations for best director and for best picture – the only time that’s happened in the same year since the 1930s. With Ocean’s, he shifted the already successful genre away from gritty and serious to stylish and fun.

Its success was all the more impressive considering the movie came out in December 2001, just a few months after 9/11 – so the alchemy had to be just right for the anxious and shell-shocked audiences who were slowly returning to theatres. First off, it was set in Vegas, the definition of escape and devil-may-careness. At the time, the city was shifting from its short experiment as a family-friendly destination back toward adult entertainment and – this is where the film helped – luxury travel. A few shots of the recently opened and opulent Bellagio Hotel & Casino, featuring Clooney in a tux and Roberts in a bright red evening dress, announced it was the place to be.

This was a chance for Clooney and Pitt to elevate their movie-star-persona game. Before 2001, Clooney was best known as ER’s Dr. Ross and Batman, but with his first Soderbergh movie, Out of Sight, and in Ocean’s, he honed his trademark ironic cool, which would see him through Oscar campaigns, political activism, tequila brands and a marriage to the most glam human rights lawyer the world has ever seen. At the same time, Pitt added new layers to his eclectic CV: the pretty boy romantic lead (Legends of the Fall; Meet Joe Black) who doubled down on out-there edginess (Fight Club; Snatch) then gave us Ocean’s Rusty Roberts, the ultimate puckish charmer, adorably snacking his way through every scene. This was the Pitt we wanted offscreen, lighting up a red carpet and falling into high-profile romances. And while he keeps himself pretty under wraps these days, we still see this side of him in films like Bullet Train and Once Upon a Time in Hollywood. 

During interviews for Ocean’s, Clooney and Pitt were paired together and leaned into their bromance – what they described as an instant friendship that developed during filming, built on professional respect and rivalry (they had both auditioned for Pitt’s breakout role in Thelma & Louise), a wariness of Hollywood fame and the love of a good prank. It was an undeniable combination. And by adding Roberts, America’s sweetheart, into the mix; as well as Damon, the boy next door (in a head fake he brought Casey Affleck on board instead of his best friend Ben); and acclaimed character actor Cheadle (who had won a Golden Globe already for playing Sammy Davis Jr. in a 1998 biopic, The Rat Pack) you had the makings of a new Hollywood pack – who’d make two sequels and crossover into each other’s films for decades to come. They weren’t as old-school and musical as The Rat Pack and they weren’t as inexperienced and messy as The Brat Pack of the 1980s. In fact, I’d call Clooney and crew The We’re-All-That Pack, just stepping into A-List territory and really enjoying the finer things in life, like when they all stayed at Clooney’s Lake Como villa while filming Ocean’s Twelve in Italy. 

Seven Decades and Counting

Ocean’s Eleven wasn’t the only zeitgeisty movie of 2001, there was Christopher Nolan’s debut, the backwards masterpiece Memento, the Jane Austen meets “chick-flick” smash Bridget Jones’s Diary, Mike Myers’ green money-making machine Shrek, and the first films in both the Harry Potter and The Lord of the Rings series. All remain part of the pop culture consciousness, but none have the IP longevity of Ocean’s – from the 1960 film to the current plans of Clooney and company to return for Ocean’s Fourteen in the not-too-distant future. Meanwhile, Margot Robbie and Bradley Cooper have announced they will executive produce and direct, respectively, a prequel in which they play Danny Ocean’s parents, pulling a job at the 1962 Formula 1 Monaco Grand Prix. 

Back in 1960, Ocean’s 11 was a box-office hit, being the first film The Rat Pack made together. Most of the gang were already performing two shows a night in Vegas and would then head to set and film into the early morning hours – smoking, drinking and palling around. To a contemporary audience, the movie’s sexist and racist zingers are painful, and Sinatra seems laconic and asleep at the wheel. It’s Dean Martin and Sammy Davis Jr., who bring the cool along with some mesmerizing musical numbers, including Martin’s Ain’t That a Kick in the Head and Davis’s E-O-Eleven. 

The ease of that movie’s robbery of five casinos was laughable, which Damon commented on during the 2001 press tour: “In the original, they pulled the heist with green glow-in-the-dark paint, I don’t think that would go over at the Bellagio.” But the one thing the original had which was lacking in all the later versions, is a true warmth and camaraderie between the characters. Sinatra’s 11 were a band of brothers, from the same paratrooper platoon in the Second World War, whose missions would have been much more dangerous than anything that happens in Vegas. Meanwhile, Clooney’s master criminals respect each other and kid around, but you wouldn’t see them standing up at each other’s weddings. Offscreen, though, there was plenty of bonding, says Clooney, especially centred around the film’s most veteran player. “The funny thing is with all these stars, with all the people you saw that were famous,” he said, “every one of us was just standing around Carl Reiner the whole time as he was telling stories.” Upon a recent rewatch, the Hollywood legend, who was part of a comedy duo with Mel Brooks, created The Dick Van Dyke Show and was the father of the late actor and filmmaker Rob Reiner, is truly the unsung hero of the movie, giving one droll line after another: “Tess is with Benedict now?” he asks about Julia Roberts and Andy Garcia’s characters. “But she’s too tall for him.”

The Friends Connection

Watching the 2001 Ocean’s Eleven with Gen Z teenagers is a trip. They like the con job aspect, but neither know nor care about any of these actors, except in their six degrees of separation to another Gen X classic, Friends. Pitt, of course, was married to Rachel (Jennifer Aniston) and guest-starred on the show as her former high school rival. Roberts also had a cameo as the victim of a school-age pantsing by Chandler (the late Canadian actor Matthew Perry) and they dated briefly in real life. Elliott Gould, who plays the outlandish financier Reuben in Ocean’s Eleven, is Jack Gellar, dad to Monica (Courteney Cox) and Ross (David Schwimmer) in the sitcom. And in a cheeky crossover with ER, Clooney and his sidekick Noah Wyle, play doctors who take Monica and Rachel out on a date. In the end, my kids were way more excited about Wyle than anyone else, as he’s beloved as Dr. Robby of The Pitt. Maybe he’d make a youth-attracting number 14 for the upcoming sequel. 

Now, 66 years from the original, 25 from the Clooney reboot and eight since Bullock’s, Ocean’s Fourteen will be entering a whole different landscape. Bernie Mac died in 2008; Reiner in 2020; and Soderbergh refuses to rejoin the franchise. Also, the novelty of A-List ensemble casts is gone – see any Wes Anderson film, Marvel movies and Knives Out mysteries, to name just a few. But this hasn’t stopped The We’re-All-That Pack from thinking this thing has legs – which is very on brand for an Ocean’s gig, where it’s never a good or bad time and there’s never a good or bad reason to run a con. When Pitt’s Rusty asks Clooney’s Danny at the beginning of Eleven, “Why do this?” His answer is, “Why not do it?” Here’s to 25 years of keeping it simple.