Skip to content

Tiffany Haddish Has a Story About Trying to Sleep With Leonardo DiCaprio

Tiffany Haddish Hit on Leonardo DiCaprio

Judging by a new profile in The Hollywood Reporter, comedian Tiffany Haddish is still excellent at giving interviews. Writer Lacey Rose had the pleasure of downing cocktails with Haddish on a cross-country flight and fielding celebrity anecdotes from the Girls Trip star. One of those stories involved the time Haddish tried to shoot her shot with Leonardo DiCaprio.

Rose wrote that she decided “to make a game of” tossing out random A-list names to see if Haddish had a story about them. The first one she mentioned was DiCaprio and the actress came through. From THR:

“Yeah, I met him at a party two, three months ago, and I asked him if he’d let me hit that,” she begins. “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?’ [Editor’s note: DiCaprio was famously a member of the “pussy posse” with pals Tobey Maguire and Kevin Connolly.] 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).’ 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?'”

If it sounds like DiCaprio is politely dodging the request towards the end of that anecdote, it’s probably because his character Arnie was a teenager with autism. Maybe she should have asked him to role-play Billy, the Southie mafia mole from The Departed, complete with the pronounced Boston accent.