Tiffany Haddish, the Best Friend America Has Dreamed Of, Speaks Candidly About Comedy, Failure, and That Alexander McQueen Dress

In February, Tiffany Haddish, the undisputed star of Girls Trip, a raunchy yet sweet story of female friendship, was leaving an office building in Los Angeles when a guard in the lobby spotted her. “Yo, Tiffany,” he called out. “Please marry me! I love you!” ­Haddish, who was dressed in jeans, a tight sweater, and her favorite Gucci fur-lined slides embroidered with her initials, turned around and faced him. “Okay,” she said in her unique Southern–by–way–of–South Central L.A. drawl. “What is your credit score?” The guard looked confused. “I can see that you don’t know what I am talking about,” Haddish continued, as her small posse of five longtime friends who work as her assistants, hairdresser, makeup artist, and stylist, looked on. “I am not interested in a man who does not know his credit rating!” Haddish looked the guard up and down. “You may be fine,” she said approvingly, “but I’m looking for someone Who. Can. Offer. Me. Security!” With that, she left the building, off with her entourage to a comedy club in Temecula, where she would be performing that night. The guard just stared: He had been Haddished.

More or less, this has been Haddish’s life since Girls Trip, which came out last July, and broke box office records in 2017. Although the film featured Queen ­Latifah and Jada Pinkett Smith, Haddish stole practically every scene: She was beautiful but willing to look ridiculous; crass, but sensitive; bold, but kind. In perhaps her most striking scene, Haddish demonstrated how to pleasure a man using a grapefruit. She was the crazy, loud, and loyal friend America dreamed of having.

Embodying classic Hollywood sophistication, Tiffany Haddish wears a Givenchy Haute Couture jacket, skirt, and earrings.

Photograph by Ethan James Green; Styled by Sara Moonves

Suddenly, Haddish, who is 38 and has been working steadily for years, was having a moment. Which, as often happens in Hollywood, led to other moments: a solo stand-up special on Showtime called Tiffany ­Haddish: She Ready! From the Hood to Hollywood! and, most important, her memoir, The Last Black ­Unicorn, which was published in December 2017. She had been working on her story for years, but when Girls Trip grossed $100 million, the book was rushed into print and quickly became a best-seller.

In Unicorn, Haddish tells a harrowing story with remarkable good humor and a total lack of bitterness. Her childhood was endlessly traumatic: Her father, who was Eritrean, abandoned the family when she was 3 years old; when she was 8, her mother was in a devastating car accident—which, Haddish writes, may have been caused by her stepfather, in an attempt to cash in on insurance money—that left her with severe brain impairment. Haddish and her four younger half-siblings were in and out of foster care and were ­eventually raised by their grandmother, who asked Haddish to leave once she turned 18 and was no longer eligible for foster care payments. Later on, Haddish had a terrible marriage but, even after she and her husband split up, Haddish couldn’t quite shake him off and wound up marrying him again. After they finally divorced for good, she was briefly homeless and lived out of her car, parking it in Beverly Hills “because,” she said, “I’ll be homeless with class.”

A Marie Antoinette extravaganza: Giambattista Valli Haute Couture gown; Stephen Russell necklace; Manolo Blahnik shoes.

Tiffany Haddish photographed by Ethan James Green for W Magazine Volume Three, 2018.

Comedy was her salvation: When Haddish was 15, a prescient social worker sent her to the Laugh Factory Comedy Camp. There, she met Richard Pryor, who gave her the advice she seems to live by: “You need to have fun.” As Haddish wrote in her book, “I try to take that philosophy and apply it to everything I do in life. That’s why I think my life turned out as good as it has. Because, all the time, I’m just trying to have fun.”

There’s another crucial element to Haddish’s personality, which hopefully won’t change as her fame grows: She’s authentic. She is not glamorous in the way of a ghetto-fabulous rapper like Cardi B, or darkly ­mysterious like her hero Pryor. She wears her difficult past lightly, but it is always there—poverty, troubled times, and the wish to succeed on her own terms are integral to her way of being. Her attitude is best illustrated by Haddish’s theory of the purse. “When I was shooting Girls Trip,” she told me, “I had a knockoff Michael Kors bag that said MLK instead of MK. Jada told me that I shouldn’t have knockoff stuff. I told her that my philosophy is, Whatever the bag costs, I should be able to keep that amount of cash in the bag. If it’s a $300 purse, I have to put $300 in cash in that purse. I do not want a bag that is more expensive than the cash I have to put in it. Things are going good for me now, so I am graduating to your Fendis and your Guccis. But I better have the cash equivalent, or I’m not buying the purse. And if things start to go wrong, I’m going right back to my knockoffs. When you’re somebody like me, who’s been homeless, clothes are not that important. Clothes are not a roof over my head, food in my ­stomach, my family’s health—that’s what money is for. But fashion helps get more money. So, we ride.”

As a fashion widow, in a Chanel Haute Couture tunic; Kokin New York mantilla; Bulgari earrings; Tiffany & Co. necklace.

Photograph by Ethan James Green; Styled by Sara Moonves

Haddish said this to me during the W photo shoot, at a remote studio near South Central L.A. The factorylike setting stood in high contrast to the couture gowns Haddish would be wearing. “I love this one,” she said of a stunning red Valentino creation. The bodice was shaped like a giant squared-off bow, and Haddish kept pulling up the corners so that they framed her face. “You know about black people and red,” she said, when I complimented the color. “Our skin loves to shine, and red brings out the shine.”

In fact, Haddish is best known for a white gown—specifically, a slinky Alexander McQueen halter with a jeweled neckline that she wore to the premiere of Girls Trip. And, again, to host Saturday Night Live. And then, yet again, as a presenter at the Academy Awards. “And I might wear it again,” Haddish told me. “Here’s the story of that dress: I hired a stylist for Girls Trip, and she said, ‘Girl, if you’re trying to make it to the next level in your career, you’re going to have to spend a little money.’ I said, ‘I’m down to look my best. Whatever it takes.’ ” The stylist brought several options, and the only one that fit her body was the McQueen. It was perfect. “I should’ve known—wasn’t no price tag on that dress. So I wear it for Girls Trip, and then they give me the receipt. When I saw the receipt, I cried. The dress was $4,122! So I’m wearing it multiple fucking times. I don’t care what nobody say—that’s a down payment on a car, that’s a medical bill. So, even though everyone says I shouldn’t wear the dress in public again, I’m wearing it.”

More than ready for her close-up in a Valentino Haute Couture dress and sandals; Philip Treacy for Valentino Haute Couture hat; Falke tights.

Photograph by Ethan James Green; Styled by Sara Moonves

On the red carpet at the Oscars, before changing for the show itself, Haddish wore a traditional Eritrean gown and cape with gold embroidery. As she told the confused interviewers, who were not used to seeing fashion that could have come straight from a museum of African dress, Haddish was honoring her late father, who died last year. Her obvious joy and pride in this tribute was striking (and not played for laughs)—and yet, in her book, Haddish’s dad is consistently ­disappearing. “But that’s Tiffany’s strength,” Jordan Peele, who cast her in his pre–Get Out film, Keanu, and in his new TV show, The Last O.G., told me. “She is loyal to family, no matter how complicated, and also to her roots. Tiffany’s authenticity is not an act. She’s not a one-dimensional person: She has the wonder of a little girl, but she also has the wisdom and maturity of a woman who has endured a lot of pain.”

In The Last O.G., which airs on TBS, Haddish plays “the one that got away”—the still-beloved ex-girlfriend of Tracy Morgan, who is a ­former drug dealer newly released from prison and trying to navigate gentrified Brooklyn. “Tiffany and Tracy have a lot in common,” Peele continued. “Both are stand-up comedians. And in both, you can see the child who went through dark times and climbed out of the wreckage. If it doesn’t kill them, people who have been through so much have a spiritual sense of how to persevere.”

A star is born in a Dior Haute Couture dress; Manolo Blahnik shoes.

Photograph by Ethan James Green; Styled by Sara Moonves Hair by Jawara for Davines at Bryant Artists; makeup by Hannah Murray at Art + Commerce; manicure by Michelle Saunders for Essie at Forward Artists. Set design by Julia Wagner at CLM. Hair by Precious Jackson at I Talent; Produced by Wes Olson at Connect the Dots; Production coordinator: Kaitlyn Fong at Connect the Dots; Retouching by dtouch ny; Digital technician: Nick Rapaz; Photography assistants: Dean Podmore, Zachary Benge; Fashion assistants: Allia Alliata, Nadia Beeman, Aisha Rae; Tailor: Isa Kriegeskotte; Production assistants: Nikki Patrlja, DeMarquis McDaniels, Doug Steans. Special thanks to Quixote, Kitchen Mouse, Studios 60

The Last O.G. is just one of Haddish’s projects. In addition to her ongoing stand-up performances, in ­September she will costar with Kevin Hart in Night School. Hart, who helped find Haddish an apartment when she was homeless, could be an electric match for her. After Girls Trip made $30 million on its opening weekend, Haddish received around 1,500 invitations, pitches, and job offers. “I waited,” she told me. “It felt fantastic! But I am hoping for someone to figure out how to do Girls Trip II. So far, that hasn’t happened. Me and the girls know how to do a sequel. We’ve mapped it out. We may have to write it ourselves.”

At the Oscars, Haddish seemed to have a definite game plan: Own this event. She struck vaguely ­Egyptian poses in her Eritrean splendor on the red carpet; ran ahead and jumped over the ropes to get to Meryl Streep; asked Streep to “be my mama” (presumably in a film, but who knows). And then, when she and Maya Rudolph presented an award during the ceremony, Haddish changed into the white McQueen gown and Ugg slippers, holding her high-heeled glittery shoes as she walked onstage. Rudolph, who was also carrying her fancy sandals, made jokes about the carefully curated display of diversity on the show. “Don’t worry,” she said, “there are so many more white people to come tonight.” ­Haddish nodded. “Mm-hmm. So many. We just came from backstage, and there are tons of ’em back there.” The next day, The New York Times (and Twitter) suggested that Haddish and Rudolph host the Academy Awards in 2019.

Caught up in a fashion whirlwind, wearing a Ralph & Russo gown; Manolo Blahnik shoes.

Photograph by Ethan James Green; Styled by Sara Moonves

Many thought that Haddish was robbed of a nomination for best supporting actress for Girls Trip. For instance, after Paul Thomas Anderson, the writer-director of Phantom Thread, saw the film, he expressed his excitement about Haddish. “She’s a really thrilling performer,” he told the Los Angeles Times. “Don’t be fooled by how funny she is. She just has a fierceness.”

“I could have been mad,” Haddish said when I asked about the Oscars slight, acknowledging that comedy is rarely honored by the academy, no matter how thrilling. “But I would always rather try to be funny in any situation. Even when people are laughing at me in a mean way, I still feel some kind of healing from it. When I get super-depressed, I’ll go on YouTube and look up “babies laughing” just to change my mood. Epic fails are funny, too,” she continued. “In failure, there can be success: By that I mean you can learn what not to do. I find the funny in a lot of failures, because I’ve had enough of them. But I am resilient: My soul is very determined. Ever since I was a little sperm, surrounded by all those other sperm that were stronger than me, had a longer tail than my tail, swam faster than me, I made my way through. I got knocked into other sperm—it was a battle, but I made it to the end.”

Milking the situation in a RVDK Ronald van der Kemp top and skirt.

Photograph by Ethan James Green; Styled by Sara Moonves

She paused. Though I was still pondering the sperm-versus-egg relationship in her analogy, ­Haddish’s point was clear: She has won. And now it was time to wage another battle, this time with an embroidered sexy milkmaid-like dress designed by Ronald van der Kemp. It was the seventh look of the shoot, and ­Haddish would be completing the transformation with a young spotted cow named Milkshake. “I used to think I wanted to be a model,” Haddish said. “But now, after today, I don’t know. People think comedy is hard, but modeling is making me cry!” She smiled and went off in search of Milkshake, who had run out of the studio in search of a pasture. “Don’t be afraid of me, little cow,” Haddish said. “Come back and I will make you laugh.”