Places Leonardo DiCaprio Has Made Out With Models, Ranked

From parties to beaches, Leo's been dipping all over the world.

Jun 12, 2015
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Complex Original

Image via Complex Original

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Complex Original

Image via Complex Original

Leonardo DiCaprio is an unstoppable, walking ball of IDGAF swagger—this is more or less general knowledge by now, if only because we here at Complex do everything we can to keep you abreast of his baller movements. And this week, Leo continued to flourish by making out with a Sports Illustrated swimsuit model while on a CitiBike.

To really conceptualize the amount of skill this took, try to imagine what would happen if you attempted to pull off what Leo did. You get a girl to go out on a date with you (not easy); you don't shave and/or dress up for this date; and just when she's expecting a nice dinner or something, you go, "Nah, we're gonna ride bikes. And not like, fancy bikes that I rented special for you—we're gonna ride these cheap-ass, city-provided bikes." I'm willing to bet that not only will this hypothetical date never kiss you on said cheap-ass bike, but she will also hate you forever. And that's before we even broach the fact that said date WAS A MODEL.

So CitiKiss got us thinking: was that the swaggiest display of affection Leo has ever achieved? We dug through all the dates, all the tropical excursions, and all the models to find out. Here are the results of that endeavor, a ranking of the places Leonardo DiCaprio has made out with models (and/or actresses, and/or musicians).

11. His Birthday Party

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The PPC (Pussy Posse Conquest): Mystery blonde

Swagger Rating: 2 out of 10 Man Buns

If you're Leonardo DiCaprio and you're not getting some at your own birthday party, then are you even Leonardo DiCaprio? This kiss was more of an inevitability than anything. Really, it was more of a flex that Leo got Kanye West to "serenade" him at this birthday party.

10. Nightclubs

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The PPC: Blonde model, Mystery brunette, Mystery black woman, Bar Refaeli 

Swagger Rating: 2 out of 10 Man Buns

Judging by volume alone, this is clearly where Leo feels most comfortable hunting. It's also the most clichéd. Kissing randos in the club? Who are you, Leo—a Goldman Sachs associate in the Meatpacking District? Yes, you think you are? Oh, okay then—keep macking.

9. A House Party

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The PPC: Rihanna 

Swagger Rating: 4 out of 10 Man Buns

So far, all the places Leo has kissed girls have been places you could kiss girls. This is one of those too. Obviously this gets bumped up a few spots by the fact that it was Rihanna though. You could not kiss Rihanna.

8. A Friend's Yacht

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The PPC: Toni Garrn

Swagger Rating: 5 out of 10 Man Buns

Now things are starting to heat up. Making out with a model off the coast of Spain on a souped-up yacht is a strong move—I think we can all agree on that. But there's a bonus here. Click on that link above, and study that amazing body language. Observe how the model grabs his face, as if she could ever hope to physically rein in his unbound charisma, while the Leonardo DiCaprio sticks his tongue out, as if to say, it's amazing how charming I am even while acting like a little shit.

7. The Warm Water of Bora Bora

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The PPC: Toni Garrn 

Swagger Rating: 6.5 out of 10 Man Buns

Kissing on the beach isn't inherently great. Everyone does it—just ask any couple from Florida. But when Leo does, he does it big. I don't know what's more impressive about this: the kiss itself, that Leo was rocking Croakie's during, the fact that just before it Leo pushed Toni Garrn straight into the water, or the fact that after it Toni Garrn took her top off and Leo proceeded to look MORE NONCHALANT THAN EVER.

6. A Lakers Game

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The PPC: Gisele Bundchen

Swagger Rating: 7 out of 10 Man Buns

HAHA IN YOUR FACE, TOM BRADY.

5. The Playboy Mansion

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The PPC: Rihanna 

Swagger Rating: 7 out of 10 Man Buns

Most guys would just make out with a Playmate if they were at a party at the Playboy Mansion. That is why Leonardo DiCaprio is not "most guys."

4. A Kanye West Concert

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The PPC: Toni Garrn 

Swagger Rating: 8 out of 10 Man Buns

Alright, just examining the setlist from this Kanye concert, which was at Madison Square Garden in 2013, when do you think Leo made the move? The beginning run from "On Sight" to "Mercy" is far too aggressive—I gotta imagine Leo was Coachella geeking at that time. If it was me, I'd have to wait until the euphoria of "Lost in the World" or the obvious choice, the romantic finale of "Bound 2." But who knows, maybe when Kanye launched into "Coldest Winter" Leo was all like, "Baby, you melt away my mistakes." *Amillionfireworksexplodeastheykiss*

3. A Daybed in Montauk

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The PPC: Kelly Rohrbach 

Swagger Rating: 9 out of 10 Man Buns

This is how amazing Leonardo DiCaprio is—in the middle of writing up this list, news breaks that Leo was caught "making out on a daybed and sipping rosé." Even though his resume is already astonishingly stacked, the guy is constantly building on it. As Kanye said at the concert where Leo made out with a model, "Bow in the presence of greatness."

2. On a CitiBike

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The PPC: Kelly Rohrbach 

Swagger Rating: 9.5 out of 10 Man Buns

For all the reasons explained in the intro, this just can't be beat. But don't worry, if there's anything I've learned about Leonardo DiCaprio, it's that he's always looking for the next big thing. Who knows what sort of greatness is on the horizon. Until then, CitiKiss is the pinnacle.

1.

Leonardo DiCaprio

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