Let Tiffany Haddish Inspire You With the Story of How She Hit on Leonardo DiCaprio


Tiffany Haddish is a truthsayer of the modern era: She’ll name names (for the most part), she’ll tell it like it is, and perhaps because she remains so lovable and charming, she’s not worried about how it lands. In short, she’s not afraid to put it all out there—not even when she’s on the cover of The Hollywood Reporter.

In her latest interview with the magazine, Haddish continues to be your personal motivator and tells the reporter about the time she just straight-up went for it with Leonardo DiCaprio:

“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.]

Unfazed by DiCaprio’s lukewarm response, Haddish chose that moment to really let her freak flag fly, which I deeply respect:

“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?’”

I love her. And I love her EVEN MORE after reading her account of meeting Roseanne Barr nearly 20 years ago and realizing THEN she was hella racist:

Haddish speaks directly into my tape recorder. “I don’t know if you know El Segundo [a coastal California town near LAX], but if you’re black and you’re driving through El Segundo, you’re going to get pulled over. I used to visit my friend Anna there, and it got to a point where I was calling the police officers by name. One day, we were walking around the neighborhood, and Anna says, ‘Oh, Roseanne lives there.’ Now, I loved Roseanne, and the next day we walked by, and she was in her yard. I say, ‘Hiiii, Roseanne.’ She looks at me (makes a disgusted face), and ran in the house. I thought, ‘Maybe she don’t want to be bothered today.’ A week later, we walk by again, and I told Anna — she’s Hispanic, but she looks white — she should say hi this time. So she says, ‘Hi, Roseanne,’ and Roseanne goes, ‘Hey!’ I thought, ‘Maybe she got to know us.’ Then I go back, like, a week later, I wave again and say, ‘Hi, Roseanne! I love your comedy,’ and she (makes the same disgusted face) and turns her head. I think, ‘Fuck that bitch.’ That was 2000, maybe 2001, so it’s not new. She been racist, why’d you all give her a TV show?”

Part of Haddish’s appeal is her story that’s now become part of celebrity folklore: how she used to be homeless, how Kevin Hart loaned her $300 and told her to make a list of her biggest career goals, how she’s crossed off just about everything on that list bynow. A loooong series of smaller gigs eventually led to Girls Trip, and the rest is history.

But in this interview, it becomes clear that even post-Girls Trip, the industry hasn’t been exactly fair to her—here, she talks openly about how much she could have made touring after her breakout, and how much she actually made:

… she had to fulfill the commitments she’d already made, including Tracy Morgan’s TBS series, The Last O.G., and a batch of suddenly sold-out comedy shows. Haddish did the shows somewhat begrudgingly. “I could’ve been paid $80K, probably $90K, a show, but because we booked those before Girls Trip came out, I was getting paid like $20K, $15K, and it fucking sucked,” she says…

Pay this woman what she’s worth!! When she told her manager that they should cancel and rebook all the gigs, his response really blew:

He’s like, ‘Tiffany, that’s not a good way to do business.’ He said that’s like being a scoundrel, and I was like, ‘No, I’m being a pirate. I want all the booty.’”

There’s another weird side to her sudden thrust into the limelight: Recently, Tracy Morgan refused to answer a question about Haddish in an interview about his show The Last O.G. (in which Haddish also stars). When other comedian friends came to her defense, Haddish tried to talk them down:

“You guys, chill. He’s probably just tired of hearing my name. It’s exhausting. I’m tired of hearing my name. I could see how that could be irritating, like, ‘Hello, I died, people. I’m back from the dead. Tiffany’s cool, but it’s me sitting here now.’ So, I get it, I’m not mad about it, I love me some Tracy.”

Fame’s not all fun and games, which is why Haddish’s sunny but extremely real disposition is not just entertaining, but also a testament to her steadfast focus, dedication, and strength. This profile does a nice job of touching on all the ins and outs of it, and reading it will probably make you respect and admire Haddish even more than you already do. Read the full thing here.

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