It’s getting heated: Our editors discuss whether or not Leo actually deserves that Oscar

As anyone who’s been following this year’s Oscar race knows, Leonardo DiCaprio has been hustling his ass. This is his fifth nomination and goddammit, he’ll be damned if he’s going to see someone else walk away it yet again. He even went so far as to kiss Maggie Smith on the BAFTA Kisscam—because obvi he doesn’t plant his lips on anyone over the age of 25—a true reflection that he’s in it to win it this year. While you can pretty much bet his name will be called on Sunday, there’s been a lot of chatter at the office about whether we want him to win it and our feelings in general on all that is Leo. Here, we recount the best snippets from our round-table discussion.

First things first: Does he actually deserve it?

Jacquelyn Francis (executive editor): I think Leo deserves to win finally if for nothing else than for what he’s done for Hollywood. He’s a box office draw. He’s a real star. He does a lot for the industry. I love that scene when he’s rolling around in Wolf of Wall Street. The Quaalude scene! He’s like, “I can’t believe I made it home without a scratch.”  I liked Matthew McConaughey, I enjoyed that film, but I thought that scene was better than anything I’d seen.

Lesa Hannah (beauty director): Gilbert Grape is his best performance.

Nicole Schaeffer (associate designer): The Departed was amazing!

Randi Bergman (executive digital editor): I thought Revolutionary Road was the best. It’s totally underrated.

Lesa: He wants that Oscar. He’s doing all the red carpets. He released that photo of him as a baby with his parents on people.com.

Derek Lall (assistant editor, MEN’S FASHION): The desperation is off-putting.

Jacq: What’s wrong with him wanting to win?

Nicole: Whoever is campaigning is desperate. The whole game is desperate. I feel like it gives him more of a humanizing [quality] to see him grovel a bit. If he was acting too fucking cool for it, we’d all think he doesn’t even care. Now he’s acting like a bit of a loser to grovel for it. I can enjoy that. I want him to win!

Derek: Part of me feels like he feels entitled to it. When he wasn’t nominated for Titanic, he was furious. Then he refused to go to the Oscars and went to New York and partied with his friends. If he wanted to show everyone that he could be a great actor, he would have swallowed his pride, showed up, and supported his film. “I’m not nominated, but I’m going to be gracious and humble. Maybe I’ll get it next time.” He was 23—he had a whole career ahead of him. It’s not like he was Peter O’Toole who was 70 and still didn’t have an Oscar.

Nicole: I listened to a podcast and they were talking about The Revenant and why he was going to win. They said that this was the first movie where his physical appearance was so different. He wasn’t attractive for once so it actually made it believable that he was a grown-up actor. I totally agree with that. It’s the most different he’s felt in any role. That’s why I think he does deserve to win for this role specifically.

Randi: I don’t get the grading of these things, though. It’s not about the best performance. It’s like, “this was challenging, so here’s your Oscar.”

Nicole: It shows his range, too. It was different. I thought it was an interesting movie. It didn’t feel long.

Sarah Casselman (senior fashion news editor): For me, it’s The Departed. I love that movie. Outside of being hot, based on acting alone…I do think he’s a really good actor. He’s not typecast. He can get into a meaty role.

Randi: I do feel like he’s typecast. He’s typecast as a leading man with a dramatic outburst.

Sarah: I feel like it’s not in the sense that he can only play one role. He’s not a one trick pony. There’s more to him than that. I also feel like he’ll look better onscreen as he ages. He’s starting to age a little bit now. He’s got some lines and he looks awesome from a cinematic point of view.

But what about the Pussy Posse?

Lesa: Let’s state the obvious: he still acts like he’s 23.

Jacq: That means nothing to me. Why does that matter?

Lesa: I have a hard time separating the personal from the professional. Leo still hooks up with girls who are 25 or under and hangs out with girls in bikinis all the time. He’s always going to a party. I’m not saying he has to get married and subscribe to society’s rules. Why should he get married? He knows he’d be bad at it. Just stop acting like you’re still 23! He’s in all these Scorsese films. He’s all for climate change. But then he turns around and all he cares about is 23 year-old swimsuit models. It’s really hard to take him seriously in that way.

Randi: What about him at Coachella fist pumping? That’s so cringey. He’s not making fun of himself. He’s seriously partying with his white hat.

Nicole: After reading that article, I thought, “why do I still like him?” I think every celebrity today is so PC. Everyone is trying to be proper. If he’s going out and being a badass and throwing caution to the wind…it’s the last vestige of that in Hollywood. We’ll never see that again.

Randi: I don’t think it’s authentic, though. I don’t mind that he was doing that. I don’t mind that he was throwing grapes or whatever. I mind that he was in a thing called the Pussy Posse. Who made that up?

Lesa: Kevin Connolly was in an interview recently and he said they never called themselves that.

Nicole: It’s also a two-way situation. I’m sure that was what they were going for. To have girls reacting to that and falling into it…I don’t think that we can hold them solely accountable for what was happening and what continues to happen.

Lesa: It’s more that he is now 41 and he’s only actively pursuing blonde swimsuit models. It makes me not respect him as a person.

Jacq: What does that have to do with his acting?

Randi: It just makes you not like him.

Nicole: The personal style is questionable. I wonder about it. Is that just him being like, “I don’t care”?

Randi: That’s what bothers me. It’s so sexist. He’s allowed to do whatever he wants. He can wear his ugly shorts and his stupid newsboy cap and his belly’s all puffed out, yet he dates Victoria’s Secret models. That’s what kills me.

Lesa: He was out everywhere playing with water guns with his belly out!

Randi: It doesn’t matter if you look like that. Just be genuine. That’s what kills me. All this being said, I’m not even anti-Leo. I think he’s an amazing actor and I’ve loved a lot of his movies. If he gets an Oscar, I’m going to be happy. That’s what kills me. It’s funny that you said you wish he’d won an Oscar for Wolf of Wall Street because that was the turning point of when I started hating him. I was like, “This is literally you and you’re gross.”

Jacq: I thought it was just a Martin Scorsese movie.

Randi: I don’t like these typecast-y things. Leo’s always in this role of the dramatic asshole. “Scorsese! Leonardo DiCaprio! We’re the best!” That bothers me. The thing about Leo is that if you’re a certain age, you’re invested in him. In the ’90s, he was such a thing and everyone was obsessed with him. Now, I just wish he was cool. I also think that as a teenybopper, your perception of him is that he’s this Romeo. He’s a wounded artist. Later on, you read about the Pussy Posse and you’re like, “Holy fuck! I can’t believe this is that person.” It ruins the whole perception of him.

Nicole: His behavior at that age makes complete sense to me. I don’t see how he could have behaved in any other way. His appearance now…I feel like it’s him reacting to being so pretty for so long. If he started getting Botox and had a six pack, I think that would make me like him less. He really doesn’t have that vanity.

Randi: I agree. I think it’s just the flipside that bothers me. I don’t care that he looks like that. It’s just that he expects his women to look like that.

Lesa: Exactly!

Jacq: I can’t judge him based on his treatment of women because that’s so pervasive.

Randi: This entire conversation wouldn’t have to happen if he was dating Kate Winslet. That would check all the boxes.

Nicole: Is it going to be a George Clooney situation? Is he going to marry someone in his 60’s and well all go, “Now we have you figured out.”

Randi: I’d be fine with that.

Nicole: If he’s not a monogamous person, he just needs to live his truth.

Lesa: It’s not about monogamy. It’s about how he’s double the age of the girls he’s dating. The girls he’s dating now were in diapers when Titanic came out.

Sarah: You’ve talked about the womanizing and modelizing, but I feel like that’s nothing new. In Hollywood, we’ve seen that for so long with Warren Beatty and Jack Nicholson. I feel like Leo’s pretty squeaky clean for the most part. We never see him falling out of a bar. What he does on his own time…so what? It’s that thing with politics. Why are we in the bedroom? There’s so much crap that goes on these days—the Kardashians, Twitter, Instagram, everything—I kind of respect the fact that whatever he does behind clothes doors is his thing. I’m judging him on his hot factor and his acting. I do think he’s a good actor. He’s the old Hollywood actor of our time.

Jacq: He’s a leading man.

Sarah: Do I think all of that 25-year-old model stuff is kind of cheesy? Yeah. I think it’s nothing new. It’s been done before. It’s not like we see him getting pulled over for DUIs and stuff like that.

Jacq: He was at the amfAR Gala a couple years back.  It was interesting to see him. He struck me as very awkward. He was a little bit on his own. He was smoking his cigarette—I could have sworn he was doing it French style. At the end of this spectacular garden was his yacht. It was docked there. He kind of holds court. God knows what’s on that boat. What stood out the most about him was that during the actual evening, every second person was thanking Leonardo DiCaprio for something or another because he’s donated his time for an auction or donated money. At a very young age, he was already a grand statesman of the scene. He was a player even amongst Nicole Kidman and people like that. They were all in awe of him, too. I was struck by that because he seemed so weird and awkward.

Lesa: He was with Gisele for like 5 years. Why didn’t Leo and Gisele end up together?! I think he said, “I don’t want the same things you do.” So she found someone else to marry.

Derek: I forgot about Gisele! That was his longest relationship.

Nicole: Will Tom Brady’s kids ever be allowed to see Titanic? That’s my ultimate question.

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