Tiffany Haddish on Hosting ‘SNL,’ Hitting on Leonardo DiCaprio, and How Kevin Hart Helped Her Get Off the Streets

Superstar comedian sits down with Howard to discuss her new book, “I Curse You With Joy”

June 6, 2024

Comedian, actress, author, and recording artist Tiffany Haddish joined the Stern Show for the first time on Wednesday, treating Howard and listeners to an epic interview covering everything from the award-winning A-lister’s humble beginnings in South Central Los Angeles to how conquering Hollywood took years of hard work and a smidgen of help from icons like Richard Pryor and Kevin Hart. In addition to her role in the upcoming blockbuster “Bad Boys: Ride or Die,” Tiffany was excited to debut her new song “Woman Up” written by Diane Warren and discuss her new memoir, “I Curse You With Joy,” which is brimming with tragi-comic tales about her tumultuous upbringing, why she once took the stage with a fake penis strapped to her, and everything in between. The essay collection also details her lauded “Saturday Night Live” appearance in 2017, which earned her both an Emmy for “Outstanding Guest Actress in a Comedy Series” and the distinction of being the first Black female comedian to ever host the long-running sketch-comedy show.

Howard wondered what it was like to break down such a monumental barrier. “Did you feel some overwhelming responsibility?” he asked.

“I felt a responsibility to myself. I felt a responsibility to 10-year-old Tiffany, that always wanted to be on the show,” Tiffany said, explaining she was especially proud of crafting that night’s monologue. “I wrote all of that.”

“Were you nervous?” Howard asked.

“It was more excited,” Haddish responded. “I felt like they was holding me back, and as soon as the doors opened I was like, ‘Yeah, I’m out here doing what I do,’ and I was just like bringing it.”

As a 10-year-old, Tiffany’s favorite “SNL” cast member was Eddie Murphy. When she befriended him in the early 2000s, Tiffany learned Eddie was a fan of hers too. “He was somebody I looked up to so much, and I didn’t want to say anything stupid,” Haddish recalled of her earliest run-ins with the comedy titan. “Little did I know he’d already been doing his research on me … I found out later … I was like, ‘You know my jokes? … You watch my stuff?’”

Online Dating, Leonardo DiCaprio, and Lenny Kravitz

Currently single, Haddish did spend some time on the dating app Bumble but didn’t find what she was looking for. “I want him to be handsome — to me,” she said before listing some notable men she’s attracted to. “Usher is handsome, Henry Cavill is handsome, Brad Pitt is handsome.”

Tiffany named another man who checks her boxes — Howard. “I think you’re handsome … I love the curly hair, I love the nose,” the actress told him.

Haddish was even more direct in her encounters with actor Leonardo DiCaprio. “I’m still working on that … I don’t think I’m his type,” she said of the star. “When I first met him, I told him, ‘I want to fuck, but only if you are your character in ‘What’s Eating Gilbert Grape?’”

When Howard mentioned rocker Lenny Kravitz, who recently made news for being celibate, the comedian grew excited. “I just got his phone number,” she revealed. “I’m trying to decide [if I should] call him and ask him about this because this might be a match made in heaven.”

This One Time at Comedy Camp … She Met Richard Pryor

As anyone who has read “I Curse You with Joy” can attest, Haddish has no shortage of hilarious and sometimes heartbreaking childhood stories. She told Howard it wasn’t always easy for her to find the right balance between tragedy and comedy, but while attending comedy camp as a kid she crossed paths with stand-up legend Richard Pryor, who gave her some much-needed advice:

“He said, ‘They’re coming to have fun, so it doesn’t matter what you’re talking about as long as you’re having fun. If you’re not having fun, they’re not having fun,’” Tiffany recalled.

Haddish puts Pryor alongside George Carlin and Dave Chappelle as one of the greatest comedians of all time. “He definitely put the smack down on comedy and changed the game and made it okay to be imperfect and be yourself on stage … to tell your truth,” she said of the late Emmy and Grammy-winning comic. “Like, it’s okay to laugh at the pain. It’s okay to say, ‘Hey man, I did this dumb-ass thing,’ and find the funny of that.”

How Steve Martin Influenced Her L.A. Story

When Howard wondered if Tiffany had read the Steve Martin book “Born Standing Up,” she confirmed she had — and then some. “I read his book like three times, and I watch all his stuff,” she said of the comedy icon.

Growing up with literacy issues, the comedian would rent Martin’s videos and tapes from the local library and treat them like a master class. “I would watch ‘The Jerk’ and all his stand-up stuff and he was so calculated,” Haddish explained. “Like the way he moved — everything was with purpose, everything meant something … nothing is done for just no fucking reason at all.”

Haddish was already doing stand-up by the time she read the book — but its contents made her realize she needed to intensify her work ethic. “I’m like, ‘I have to step my work level up. I have to invest more time in how I’m going to talk,’” she remembered.

Though Tiffany finally got to meet her hero not too long ago — he signed her autograph book — she still wants to pick his brain. “I really want to ask him a thousand questions because he was killing it at a time where there was definitely no social media,” the comic marveled before pointing out Martin would have droves of people waiting to get into his shows back in the 1970s. “How do you create that line down the street without the social?”

How Kevin Hart Helped Her Move Out of Her Car

Making it in show business is no easy feat, even for someone as gifted as Haddish. At several points while climbing the comedy ladder, she found herself living out of her car. “And this was a Geo Metro,” she told Howard. “It’s not like it was a damn Tesla [or] sedan.”

Living in her car meant moving her belongings into storage and showering at places like homeless shelters and gyms, all while working day jobs and any comedy gig she could get. “I felt like, ‘This is rock bottom,’” Tiffany recalled.

Her persistence paid off, however, and she eventually both carved out a name for herself and earned the respect of her peers, including comedy icon Kevin Hart, who took notice of Tiffany’s talents while she was struggling and gave her $300 to move into a hotel. “I do have great love for him,” Haddish said of Hart. “That’s my big brother. Even though he’s smaller than me.”

Success (and a Billboard) Is the Best Revenge

Tiffany was just eight years old when her mother was in a car accident so severe that it left her unable to properly parent. While waiting for her loving grandmother to gain custody of her, Tiffany was forced into a violent foster care system where she was frequently attacked by bullies. “I had to fight,” Haddish said, explaining that she soon learned to talk her way out of almost any situation. “I had developed [really] good communication skills.”

Even so, the bullying and other hardships took their toll. “I had like a full-on breakdown … I was crying every day, and I ended up in therapy,” she recalled. “It felt like I was everybody’s punching bag.”

Thankfully, Haddish is in a much happier place these days, but she told Howard she isn’t above getting a little revenge on those who’d put her down. “Oh, I can’t [succeed]? Watch me be more successful than you,” she said, joking that her ultimate goal involved plastering her face on billboards where her detractors lived “so that when they walk out of the house they just see me.”

Donating Her Eggs

Years before she found success, Haddish turned to a method many young women use to make ends meet – she sold her eggs to a fertility service. “There might be some babies out there with my blood in them, with my DNA in them,” the comedian admitted before adding that she used the $5,000 fee to mostly pay off some credit card bills. “It’s not the most comfortable – you inject yourself and then you drop like 25 eggs at a time. You can’t have sex for like six weeks or you might get pregnant with like a litter of kids.”

The facility promised a bonus if any of her eggs were used, but so far Haddish still hasn’t heard anything. “I registered on 23andMe to see who lines up — I haven’t had any matches at this point,” she told Howard.

“I Curse You With Joy” is available now.