Tiffany Haddish tells a hilarious story about hitting on Leonardo Dicaprio

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By VT

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Tiffany Haddish stole the show in the movie Girl's Trip, and now she's proving she gives the best interviews. Who wants to hear actors talk about their craft? So boring. Last March, Tiffany told a story about an actress biting Beyonce's face at a party.

Also, the comedian hasn't been shy about flirting with celebrities. Hey, if you blew up, and found yourself in the room with gorgeous A-listers, you'd probably do the same. During a post-Oscars interview, she revealed she met Brad Pitt in the elevator. "He said in one year, if he's single and I'm single, we gonna do it—so, you know what that means..."

[[instagramwidget||https://www.instagram.com/p/Bf9Dq0tnfkP/]]

In a new interview with The Hollywood Reporter, Tiffany told another hilarious story. At a party, she hit on Oscar-winning actor Leonardo DiCaprio. And girl's got game.

"Yeah, I met him at a party two, three months ago, and I asked him if he'd let me hit that. He's like, 'Tiffany, you're so funny.' I'm like, 'I'm serious.' And then he goes, 'I mean, I'd do it, but …' I was like, 'Come on, wasn't you in a squad? The coochie squad or something?'

(When he was younger, Leonardo DiCaprio was famously a member of the "Pussy Posse," which is exactly what it sounds like: a group of young men who bonded over their love of getting laid. The posse included stars like Tobey Maguire, David Blaine and Kevin Connolly, although Leo was their "leader." Apparently, in the mid to late 1990's, they partied all over New York City, and had some pretty wild times.)

[[youtubewidget||https://www.youtube.com/watch?v=wbUbjJb1BEo]]

Anyway, back to Tiffany hitting on Leo! She continued:

"I told him, 'My only stipulation: I wanna do it with you as your character in What's Eating Gilbert Grape.' He starts bustin' up laughin'. 'Why?' he asks, and I say, 'Cause I feel like that performance deserves a real reward and that reward is this (gestures at her own body).'"

(In the 1993 drama What's Eating Gilbert Grape?, Leonardo played a mentally handicapped teenager named Arnie. He received his first Oscar nomination for the role. And yes, the idea of him playing the character in bed with Tiffany is so wrong, but so funny.)

[[youtubewidget||https://www.youtube.com/watch?v=wpSGFets1oM]]

Anyway, Leo tired to steer the conversation back into normal territory, but Tiffany wasn't going to give up that easy.

"He starts goin' into how he got into the role, how he worked with these kids and all this stuff, and I'm just listenin' and listenin', like, 'Mmm-hmm, mmm-hmm.' I finally go, 'All that's good, I just need to know, When's this gonna happen?'"

The story ends here,  unfortunately. I guess we'll never know if Leo warmed up to the idea of a doing little Arnie Grape roleplaying. Well, hopefully Tiffany has a long Hollywood career, so she can continue to awkwardly hit on A-list stars, and tell us all about it.

Tiffany Haddish tells a hilarious story about hitting on Leonardo Dicaprio

vt-author-image

By VT

Article saved!Article saved!

Tiffany Haddish stole the show in the movie Girl's Trip, and now she's proving she gives the best interviews. Who wants to hear actors talk about their craft? So boring. Last March, Tiffany told a story about an actress biting Beyonce's face at a party.

Also, the comedian hasn't been shy about flirting with celebrities. Hey, if you blew up, and found yourself in the room with gorgeous A-listers, you'd probably do the same. During a post-Oscars interview, she revealed she met Brad Pitt in the elevator. "He said in one year, if he's single and I'm single, we gonna do it—so, you know what that means..."

[[instagramwidget||https://www.instagram.com/p/Bf9Dq0tnfkP/]]

In a new interview with The Hollywood Reporter, Tiffany told another hilarious story. At a party, she hit on Oscar-winning actor Leonardo DiCaprio. And girl's got game.

"Yeah, I met him at a party two, three months ago, and I asked him if he'd let me hit that. He's like, 'Tiffany, you're so funny.' I'm like, 'I'm serious.' And then he goes, 'I mean, I'd do it, but …' I was like, 'Come on, wasn't you in a squad? The coochie squad or something?'

(When he was younger, Leonardo DiCaprio was famously a member of the "Pussy Posse," which is exactly what it sounds like: a group of young men who bonded over their love of getting laid. The posse included stars like Tobey Maguire, David Blaine and Kevin Connolly, although Leo was their "leader." Apparently, in the mid to late 1990's, they partied all over New York City, and had some pretty wild times.)

[[youtubewidget||https://www.youtube.com/watch?v=wbUbjJb1BEo]]

Anyway, back to Tiffany hitting on Leo! She continued:

"I told him, 'My only stipulation: I wanna do it with you as your character in What's Eating Gilbert Grape.' He starts bustin' up laughin'. 'Why?' he asks, and I say, 'Cause I feel like that performance deserves a real reward and that reward is this (gestures at her own body).'"

(In the 1993 drama What's Eating Gilbert Grape?, Leonardo played a mentally handicapped teenager named Arnie. He received his first Oscar nomination for the role. And yes, the idea of him playing the character in bed with Tiffany is so wrong, but so funny.)

[[youtubewidget||https://www.youtube.com/watch?v=wpSGFets1oM]]

Anyway, Leo tired to steer the conversation back into normal territory, but Tiffany wasn't going to give up that easy.

"He starts goin' into how he got into the role, how he worked with these kids and all this stuff, and I'm just listenin' and listenin', like, 'Mmm-hmm, mmm-hmm.' I finally go, 'All that's good, I just need to know, When's this gonna happen?'"

The story ends here,  unfortunately. I guess we'll never know if Leo warmed up to the idea of a doing little Arnie Grape roleplaying. Well, hopefully Tiffany has a long Hollywood career, so she can continue to awkwardly hit on A-list stars, and tell us all about it.