Filmmaking Lessons from “The Ocean’s Trilogy” — ‘Ocean’s Eleven’

Ocean’s Eleven was released in 2001. The world was kind of in a weird place. It felt like everything was on fire. I was nine years old and I was at the Regal Theater in New Rochelle. I was watching one of the coolest movies I have ever seen. George Clooney and Brad Pitt, the epitome of gentlemen thieves, were on the screen looking like absolute rock stars; movie royalty. At the end of the film, the villain, Terry Benedict (Andy Garcia), a ruthless mogul and casino owner, has just called the SWAT team to stop thieves from robbing his vault. The thieves escape and the SWAT team leaves. Terry Benedict stands in the middle of the vault and tries to piece together what just happened. His second in command asks him on the walkie-talkie, “What happened to all that money?” We cut to the SWAT team walking through the casino floor, bags in hand. One of them flips up their helmet to wipe the sweat off his brow. It’s Brad Pitt.

The theater applauded. Applauded. At the time, that didn’t make sense to me. Brad Pitt wasn’t in the audience. He wasn’t backstage waiting to sign autographs. They just applauded. They couldn’t help but physically react in unison. It was the moment that I realized how powerful movies can be. It also made me want to rob casinos but that’s another thing.

Steven Soderbergh had just won the Academy Award for Best Director for the film, Traffic. It’s an amazing film. It’s also the film that’s responsible for Mexico looking yellow in every single American-made crime thriller that takes place there (Looking at you, Breaking Bad). He beat Ridley Scott for Gladiator. He beat Ang Lee for Crouching Tiger, Hidden Dragon. And he beat Steven Soderbergh for Erin Brockovich. That’s right. One of the people he beat for the Oscar, was himself. The man beat himself. After winning an Oscar for a thought-provoking documentary-style ensemble film about the illegal drug trade, he decides to do what any director would do: Make a heist film starring the biggest movie stars at the time. Ocean’s Eleven is the first installment in one of the most famous trilogies in American movies. It has everything: Movie stars, glamour, suspense, laughs, and fun. But despite what everyone thinks, these aren’t just breezy caper movies. The trilogy is Steven Soderbergh’s thesis on making movies, and by extension, Hollywood itself.

YOU’RE EITHER IN OR YOU’RE OUT

Remakes are a controversial subject. Most of them are terrible. Usually, they are the exact same movie with nothing new to say. A good amount of them make money. Nostalgia is a hell of a thing. But every once in a while there are remakes that are just as good or better than the original: John Carpenter’s The Thing, Scarface, and the remake of Suspiria to name a few. Honestly, that’s about it, counting Ocean’s Eleven.

The original stars Frank Sinatra as Danny Ocean and the rest of the Rat Pack as the rest of the eleven. Danny Ocean and his war buddies decide to rob Las Vegas casinos. The Rat Pack was the living embodiment of cool. That means Ocean’s 11 is a classic. Far from it, actually. It sucks. It really sucks. The only good thing to come out of that movie is Sammy Davis, Jr. singing Eee-o Eleven and the final shot where the eleven lose their money and roam the streets in despair. Other than that, you can skip it. I don’t understand how a movie starring Frank Sinatra, Dean Martin, and Sammy Davis, Jr. robbing Las Vegas casinos is boring; the cure to insomnia.

The remake is the same in premise only. Danny Ocean gets a crew together to rob Las Vegas casinos. The similarities stop there. It’s a completely different movie. This is what a remake should be. Having said that, asking someone to play a role originated by fucking Sinatra is a pretty tall order. In the remake, George Clooney plays Danny Ocean, an ex-con whose wife divorced him while he was in prison. When he gets out, he meets up with his best friend and plans the robbery of three Las Vegas casinos at the same time. Danny’s best friend is Rusty Ryan. He’s played by Brad Pitt. If you ever want to show someone what a movie star is, make them watch these movies. They have screen charisma, charm, and good looks. True papi chulos.

The movie doesn’t ask Clooney to be the new Sinatra. He’s a throwback to the stars of the Golden Age of Hollywood. He’s Cary Grant. He’s Paul Newman. Handsome men who were not only great performers but were more than willing to poke fun at our preconceptions of them.

If George Clooney is Paul Newman, then Brad Pitt is Robert Redford. This duo is just as iconic. Soderbergh is a fan of classics from the New Hollywood era in the 70s. The Rat Pack references are surface-level. If Clooney and Pitt are Newman and Redford, this movie is The Sting; a caper classic that was good enough to win the Oscar for Best Picture in 1973. Soderbergh aimed to make an old-school Hollywood classic.

Ocean’s Eleven loves to cut ass on the artifice of Hollywood and the absurdity of making movies. Matt Damon plays a rookie pickpocket looking to move onto bigger scores; the same way Matt Damon, a talented young actor at the time was about to evolve into a movie star in his own right. Rusty’s introduction is him teaching young TV stars how to play poker. Danny meets up with him and they con the stars into giving them a lot of money. When they leave the club, the paparazzi swarm Topher Grace instead of Clooney and Pitt; the real movie stars.

Danny and Rusty have one of the best friendships depicted in film. They finish each other’s sentences. They know each other so well, they can address what the other person is thinking without saying a word; something that’s essential to making a film. Danny is the director. He’s big picture. He has imagination and vision and he knows what the end result should look like. He brings his idea to his producer, in this case, Rusty, who figures out the logistics and executes it.

YOU BET BIG AND THEN YOU TAKE THE HOUSE

The most important aspect of making a movie is the crew. The producer has to assemble the crew with input from the director. And the crew is filled with a cast of incredible character actors and stars (Matt Damon, Don Cheadle, Bernie Mac, Elliot Gould, Scott Caan, etc.) They all have their specialties that are equivalent to crew positions on a film. Linus Caldwell (Matt Damon), Frank Catton (Bernie Mac), and Saul Bloom (Carl Reiner) are con men. They’re the actors. Livingston Dell (Eddie Jemison) is the surveillance expert. He stares at screens all day after hacking the security cameras to make the guards see what he wants them to see. He’s the editor. Basher Tarr (Don Cheadle) is the explosives expert. He’s special effects. The Amazing Yen (Shaobo Qin) is the “grease man;” the acrobat. He’s the stunt man. The Malloy Brothers (Casey Affleck and Scott Caan) handle the cars and other menial tasks that make sure the caper goes off without a hitch. And Reuben Tishkoff is financing the whole thing. He’s the movie studio. He’s a legendary on the downslope of his career aching to have success again. Like Bob Evans in the latter half of his career.

Danny Ocean plans to rob three casinos owned by Reuben’s rival, Terry Benedict (Andy Garcia). Terry is powerful and ruthless and has ruined the lives of cheaters and thieves in the past. The plan is to steal $160 million. The plan has to be meticulously planned. The crew researches and builds sets they can rehearse in. Problems arise and they have to solve them on the fly. But there’s one detail that complicates the whole thing. Terry Benedict is dating Danny’s ex-wife, Tess (Julia Roberts), who he is very much still in love with. They divorced when he was locked up and she’s not happy to see him when he meets her in the restaurant. Sure, there are millions of dollars at stake, but the real reason he’s there is to win Tess back.

This all leads to the moment that Danny has arranged. Benedict suspects Danny is the one behind the robbery and confronts him. Livingston has hijacked the surveillance and calls Tess to turn on her TV. She watched the confrontation. Danny asks Benedict “What if I told you I could get your money back if you give up Tess?” Benedict says yes. Danny has used the specialty of his crew to show his audience, in this case, Tess, the point of this whole thing: To show the person he loves most that he cares about them. A perfect movie moment.

This film ends with the crew looking at the Bellagio Fountain at night. Steven Soderbergh plays Clair de Lune. The crew looks at the fountains and part their ways; like a film crew. A crew makes something special working as a team and that’s it. On to the next job.

The last image is Danny riding in a car with his best friend, Rusty, and the love of his life, Tess. He’s made a movie and now he’s with his loved ones. That’s a good life.

This article first appeared in The Cinemonograph Collection