Everyone has those movies that they watch over and over again.
Most of us probably have at least a handful of comedies we go back to on the regular. Jim Carrey, Eddie Murphy, Will Ferrell, Adam Sandler, and Bill Murray, to name a few, are beloved icons of the genre with stacked libraries worthy of return visits. And who doesn’t love a rom-com comfort watch? I dare you to dial up When Harry Met Sally… or Crazy, Stupid, Love. and not have a great time. Some of us might repeatedly fire up a dark thriller like Zodiac or The Silence of the Lambs, or settle in for an action classic, like Die Hard or The Terminator. And you can’t go wrong with escaping into a beloved sci-fi or fantasy universe, à la Star Wars or The Lord of the Rings. But there’s another, more specific genre of film that is pretty much always rewarding on the rewatch.
I’m not sure how many kinds of heist movies there actually are, but I do know that there are at least two. First, you have violent, intense, character-driven flicks, like Heat and Den of Thieves. Then, you have the fun, stylish, “getting the gang together” brand. I’ve written about The Sting for this column, and while the Paul Newman/Robert Redford classic might be the OG entry in the second category, its modern-day descendent could very well define it.
Ocean’s Eleven, Steven Soderbergh’s 2001 heist comedy, is a remake of the 1960 film Ocean’s 11, starring the Rat Pack – Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop. Pretty cool cast! With his version, the first film in a fantastic trilogy, Soderbergh also opts for the “Let’s get a bunch of stars together and have them do and say cool stuff” strategy, which, unsurprisingly, is a 450-foot home run to dead center.
The movie’s plot is simple enough on the surface, but it has a bit of complexity to it (we’ll get to that in a bit). Here’s the gist: Danny Ocean (George Clooney) is a professional thief freshly out of the pokey after doing a four-year bit. He travels from New Jersey to L.A. to link up with his buddy and fellow heist man, Rusty Ryan (Brad Pitt). This isn’t just a casual reunion, where a couple pals throw back a few cold ones and reminisce about old times; after his stretch in prison, Danny’s itching to get back in the saddle. He pitches his idea to Rusty, and it’s ambitious, to say the least: Danny wants to simultaneously rob three Las Vegas casinos – the Bellagio, the Mirage, and the MGM Grand – owned by cutthroat businessman Terry Benedict (Andy Garcia). Rusty’s initial hesitance is short-lived – these two are in it for the love of the game, and this might be the biggest job conceivable; the definition of “high risk, high reward.” It’s the kind of job only the best of the best would even consider trying, let alone actually pull off. It doesn’t take Danny long to get Rusty on board.
Now, to execute a robbery of this scope, Danny and Rusty need two things: a substantial bankroll, which they secure from wealthy friend and Benedict rival Reuben Tishkoff (Elliot Gould); and a large crew.
Folks, when it comes to movie tropes, it’s hard to do better than “getting the gang together.” Honestly, the only thing that might top it is “getting the gang back together.” This is a common heist movie beat, and Ocean’s Eleven does it as well as any of them. We have an Avengers-level crew assembling on our hands here. Danny and Rusty methodically build their conman all-star team, with each person bringing their own specific skill set to the operation.
This brings us to the cast, which is absolutely loaded. We have to start with Matt Damon as pickpocket Linus Caldwell. Mark Wahlberg was apparently up for the role, but he turned it down to star in Tim Burton’s Planet of the Apes (yikes, in my opinion!). I’m a Wahlberg fan, but this casting switch-up was to the benefit of Ocean’s Eleven, because Damon is outstanding. While Linus is undeniably a gifted thief, he’s still pretty green when he joins the crew, and yet he still wants to be taken as seriously as veterans like Danny and Rusty. Damon brings this hysterical, sort of awkward kid brother energy to the role that gels perfectly with how naturally cool Clooney and Pitt are. Damon’s okay with being the butt of the joke, and he nails the “try-hard” dorkiness the character needs.
The rest of the cast is an A-plus across the board. Along with Danny, Rusty, Linus, and Reuben, the crew is rounded out by wheelmen Virgil and Turk Malloy (Casey Affleck and Scott Cann, both doing phenomenal, hilarious work as bickering brothers), conman Frank Catton (the late, great Bernie Mac), explosives expert Basher Tarr (Don Cheadle), tech genius Livingston Dell (Eddie Jemison), acrobat-turned-grease man Yen (Shaobo Qin), and retired conman royalty Saul Bloom (the legendary Carl Reiner).
Oh yeah, Julia Roberts is in this. Did I mention that? It seems like an important bit of information. Roberts, one of the great movie stars of her generation, delivers in her typical top-tier fashion. She doesn’t have a lot of screen time, but she makes what she has count. Roberts and Clooney have outrageous chemistry in their scenes together, and Pitt at this point in his career is on the cusp of being the biggest star on the planet, yet she still nearly blows them both off the screen. I cannot stress enough that almost no one else could do this. Maybe Meryl Streep? Is that the entire list? Anyway, Roberts is lights out, as usual, and her movie star powers are cranked to 11. No notes.
The beating heart of Ocean’s Eleven is the chemistry between Clooney and Pitt. In a recent column on Butch Cassidy and the Sundance Kid, I mentioned that Clooney and Pitt in the Ocean’s movies are probably the contemporary version of ‘60s Newman and Redford. Look, you could write the names of 20 A-list stars, throw them into a hat, pick two out, put them in a movie together, and the final product would likely be at least perfectly fine. Would a buddy cop movie with Robert Downey Jr. and Denzel Washington work? Could Viola Davis and Emma Stone lead a period drama? I mean, probably. But for a film to jump up a notch, there has to be some level of chemistry there, and much like Newman and Redford, Clooney and Pitt have it in spades. It obviously helps that these are two of the best-looking people who have ever stood in front of a camera, and they radiate raw charm and charisma, but they are also very believable pals who can play off each other with ease, in both serious and comedic circumstances. It’s like watching an awesome tennis match, except no one is trying to win, or even score points on the other guy; they just hit the ball back and forth, setting each other up, allowing the other showcase their strengths, and lock into a mesmerizing rhythm. It’s movie stardom at its finest.
I mentioned earlier that this movie, while pretty simple from a plot standpoint, has layers of complexity to it. Without spoiling anything important (going into the job blind ensures it can be experienced with maximum enjoyment), it’s worth noting that the heist itself is constructed of numerous ongoing grifts. These cons are crucial to the operation’s success, yet they’re only briefly mentioned and never fully explained through exposition. While Danny and Rusty are brainstorming how to make the job happen, Rusty declares that it’ll require a number of cons, including a Jim Brown, a Miss Daisy, two Jethros, a Leon Spinks, and “the biggest Ella Fitzgerald ever” – and it’s left at that. Now, one could probably take the names of the cons and figure out which name applies to which grift carried out during the job, but that’s left totally up to the viewer. Personally, I enjoy the mystery of it, but for those who want to dive a little deeper, I’m sure someone on the internet has pieced the puzzle together.
Ultimately, these cons, along with references to past jobs and former and current thieves, suggest that a wider universe of professional criminals exists, and they put the heist at the center of Ocean’s Eleven into perspective. To reiterate, Danny and Rusty genuinely love this line of work, and this is not just any another job; it’s the kind of job that’ll live on forever. Its brilliance in conception and execution (not to mention its colossal payday) will be permanently cemented in conman lore, and this acts as a motivating factor for the crew. I mean, who doesn’t want to be a legend – and a rich one at that?
I’ve seen Ocean’s Eleven many times, and I think I have a roughly 80% grasp on how the heist is actually pulled off (and truthfully, that’s probably a generous estimation). But I think this lends credence to the notion that Ocean’s Eleven might be the most rewarding rewatch out there. You can absolutely fire it up casually, and pop in and out of the room or check your email a few times, and still have a ton of fun. But if you want to truly understand how the job goes down, then a full-on lock-in is required. This idea can be intimidating from a viewer’s perspective; I mean, who wants to dedicate two hours to a movie and come out on the other side saying, “What the heck just happened? What did I just watch?” But in the case of Ocean’s Eleven, the sheer exhilaration it offers makes the dedication of time and keen observation more than worth it, not just on the first watch, but all those that come after, too.
The other two entries in the Ocean’s trilogy are also a great time. Twelve finds our boys (and Roberts) on a European excursion, and Thirteen features later-career Al Pacino bringing his trademark heat, which, I mean…enough said. But Eleven is the crown jewel; it’s effortlessly cool, and a total blast.
In simply tremendous news, it looks like another Ocean’s movie is in the works. You think we need one more? You think we need one more. Alright, we’ll get one more.
Jalen’s columns, “Movies You Gotta See” and “The Free Play,” can be found online at www.medium.com/@jalenmaki.
Follow Jalen on Letterboxd at www.letterboxd.com/jalenmaki182/ to see what he’s been watching.
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