A Totally Speculative Conversation About Who's Cooler, DiCaprio or Clooney

Esteemed bros.

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Complex Original

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George Clooney, per George Clooney, can play basketball. Leonardo DiCaprio, per George Clooney, likes to play basketball—with a group of guys who maybe can't play. 

This bit of dudeful gossip came out of a recent Esquire profile with the most handsome salted and peppered mug in all of Hollywood. What the profile is quick to call shots between the two sounds more like regular shit-talk, the kind of thing that you expect on the court and then off the court whenever any of the players get the notion.

Clooney in his magazine profile, busting balls while hanging out with his dog, Einstein, cuts a different image than what DiCaprio showed the world last Sunday, when he celebrated his 39th birthday in the company of 2 Chainz and Kanye West, both of whom performed at the party. There's a 13-year age difference between Clooney and DiCaprio, but both have filmographies that include some of the biggest movies in recent history. They have a healthy competition, the kind of thing you admire in rappers like Kendrick Lamar and everyone who tries to rap at him.

These much harped upon events in the lives of the stars—Clooney talking light-hearted shit with Esquire; DiCaprio wearing a cabbie's hat low on his face while basking in the virtues of big booty hoes—set the stage: One of these men is cooler than the other, and Complex deputy editors Donnie Kwak and Justin Monroe, along with senior staff writer Matt Barone and associate editor Ross Scarano, blended hearsay, gut feelings, and maybe some facts for a purely speculative conversation about which one seems like the better dude and actor. It's a weird time. Enjoy.

Donnie Kwak: Did you guys watch the video clips from Leo's birthday with 2 Chainz and Kanye West? He definitely seems super-bro in them. Not that there's anything wrong with that. I'd probably rather hang out with DiCaprio than Clooney.

Ross Scarano: Based on the little I've read, DiCaprio seems like a jackass. His "Pussy Patrol"—excuse me, "Pussy Posse."

Donnie: You don't want to sit next to Clooney at dinner, man.

I bet Clooney plays basketball like a gym rat. Not sure if Leo's out there all the time. Probably chest-pressing models, Leo is. —Justin Monroe

Justin Monroe: Why not? Clooney seems like a lot of fun. Leo might be cool on his own but the entourage would be the worst. Dudes jockeying for prime ball-licking positioning. I bet one of them has a biz card with the title SKANK 'N' DANK WRANGLER.

Ross: I'd put money on that as well.

Donnie: Clooney is so self-important man.

Justin: I think he has a sense of humor and isn't pompous about himself. But honestly, what the fuck do I know? They might both be raging cocks, just the most insidious assholes ever born.

Donnie:Esquire is hyping up the Leo comments, and it worked because it got picked up. What Clooney said was kind of innocuous and, in any event, the fact that Clooney is aghast that people talk trash on the basketball court, well, sorry, Sir Clooney—they weren't going to debate Syria. You talk shit, sometimes you back it up, sometimes you get clowned. It doesn't mean you don't have the right people in your life. Get off it.

Justin: That struck me as all out of context. Clooney is a noted basketball player.

Donnie: Noted for not being terrible. That's about it.

Justin: He obviously is aware of this thing called shit talking. This isn't him being a grumpy old man, this is him SHIT-TALKING because his team sonned DiCaprio's team. I think it's about as serious as any of our fantasy football league banter.

Matt Barone: Who do you think would win in one-on-one: Clooney or DiCaprio?

Justin: I bet Clooney plays like a gym rat. Not sure if Leo's out there all the time. Probably chest-pressing models, Leo is.

Ross: Skinny models, though.

Matt: I'd put money on Clooney.

Donnie: Who's cooler?

Ross: Clooney.

Donnie: I think Leo's cooler.

Has Clooney ever been good in a movie in which he didn't play Clooney? —Donnie Kwak

Justin: Leo gets points for his love of rap but I've always had some issues with him. I was a much bigger fan of Leo in the Gilbert Grape era than that weird in-between time when he still looked 16 but was supposed to be a grown man in roles. That made me dislike him a little as a person because, for me, he fucked up every movie he was in. Which was NOT COOL.

Ross: When did he click for you again? Feeling like it might be The Departed, actually. Which might make me late to the Leo party.

Justin: People loved him in The Departed and I still hated him. So I guess I changed my mind with...Shutter Island?

Ross: Do I love any of Leo's movies or performances? I might not.

Donnie: Has Clooney ever been good in a movie in which he didn't play Clooney?

Matt:Burn After Reading.

Ross: Yes to what Matt said, and to Donnie: DiCaprio has just as many tics as Clooney, and you see them all the time. DiCaprio in Shutter Island is DiCaprio in Inception is DiCaprio in Revolutionary Road. Well dressed guy trying to keep from cracking up despite tremendous personal/societal pressure. He cracks up and yells in each one. Is sad about a woman in each one. Yells some more. Still looks good. I don't think it's fair to knock Clooney for being Clooney, when he does it so well.

Donnie: At least DiCaprio tries. Cloonely playing Clooney makes him not as impressive of an actor to me.

Justin: I loved DiCaprio in Django Unchained.

Ross:Django is probably the best thing DiCaprio has ever done.

Donnie: Would Clooney even try Calvin Candie? C'mon now. The quintessential Clooney role is Danny Ocean.

Ross: Clooney is awesome in O Brother, Where Art Thou?, a role that pokes fun at his essential Clooneyness.

Justin: I don't blame Clooney for Hollywood casting him as a suave older fellow with salt and pepper hair. His movies have different enough vibes for me.

Donnie: I don't knock Clooney for taking little jabs at Leo, he's like 15 years older, it's an older-brother type of vibe. But Leo is a better actor and will be remembered more for his acting, not being this cool guy that all white men aspire to be like. Well, white and black men, maybe.

Justin: I definitely prefer Clooney's catalogue. I don't consider Leo to be a chameleon.

Ross: I'd take Clooney's catalogue over Leo's every time.

Donnie: Leo is actually aggressively uncool, if you think about it. Look at his non-movie gear. He wears frat-bro hats.

Justin: Which kind of bothers me. It's like he's saying, "Yeah, I know I look terrible with these clothes but I'm made of money so you still want to suck this d."

Donnie: Do you think Leo in his 50s will be taking shots at Jessie Eisenberg?

Ross: Has Leo ever had a role where he makes fun of the idea of Leo?

Donnie: Leo's a little less self-aware than Clooney is. Clooney is the dude that pretends like he doesn't care but cares a great deal, the secret narcissist. Clooney "evolved" over the years, new friends, new social stratosphere; I think Leo's just the same dude, more or less. For better or worse.

Ross: Why are we discounting evolving? What's wrong with new friends? Isn't Drake saying "no new friends" what makes him a cornball?

Donnie: I'm just making a point of comparison. Clooney believes that he belongs in public office. Or that he has some higher calling. He's a little self-important is all. That's why I wouldn't want to sit next to him at dinner.

Justin: Another question: Who would you rather be in a foxhole with?

Ross: Clooney might try to take a bullet for me to get the best medal and congressional recognition. 

Matt: I think Clooney would have my back more than Leo, so I'd bring him into the, um, foxhole.

Donnie: I probably wouldn't want to sit next to Leo at dinner, either, actually. But Leo is just what he is—an actor. And I think he acts better than Clooney. That's all. I don't buy all this Clooney "mystique" and Lake Como and dating barristers and all of this crap. He's Danny Ocean and dude from Facts of Life. Has Clooney ever played a truly unlikeable scamp in any of his movies?

Justin:Batman and Robin.

Ross: He's unlikeable in Burn After Reading. Not sure about the scamp part. I am sure that this is the most I've ever seen the word "scamp" used in a single conversation.

Matt: He's not very likable in The Ides of March.

Donnie: Would he ever accept a role to play one? Would he play Calvin Candie? Or would that be at odds with the EVERYBODY LOVES CLOONEY narrative. He's like the male Julia Roberts.

Ross: Oh my god, you did not! Julia Roberts?! 

Justin: That's something that I blame Hollywood for, though. You tend to get hero or villain status.

Ross: DiCaprio does deserve props for that role, though. I could see Tarantino using Clooney in an anti-Clooney way later in Clooney's life. (I just hit the point where "Clooney" looks like a fake word to me, FYI.)

Justin: Maybe as a zombie with his perfect square jaw hanging off by a thread of flesh.

Matt: Clooney Scamp.

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