Tiffany Haddish Shares Emotional Tie to Sports Illustrated Cover

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Tiffany Haddish Shares Emotional Connection to Sports Illustrated Milestone

Tiffany Haddish is known for bringing the laughs, but the story behind her latest career milestone touches the heart.

After the comedian landed a cover in the 2026 Sports Illustrated Swimsuit issue, she shared that the reason why she was so thrilled about the honor was about far more than vanity.

"I wanted to follow in my grandmother's footsteps of being a model," Tiffany exclusively told E! News at a May 14 launch party in New York. "I feel like this is my way of honoring my grandmother and her legacy. So it's a big deal for me."

"It's more than just being pretty," Tiffany continued. "This is like my ancestors are all over this. And I'm very, very happy, very, very grateful."

Tiffany couldn't help but get choked up when describing the "full circle" moment. "I'm sorry, I'm getting emotional," she confessed before landing one of her trademark jokes. "I'm ovulating or something, I don't know."

Securing the legendary cover was a family dream come true, but the Like A Boss star shared that another famous family was a huge part in making it happen. After all, she learned she would become an SI model during an elaborate surprise at Paris Hilton's house.

"And the way that I found out that I got the cover was my manager blindfolded me [and] took me over to Paris Hilton's house," Tiffany said, explaining that when she opened her eyes, she was there with Paris and a cake. "I looked at the cake and it said, ‘You are a cover swimsuit model for Sports Illustrated.' And I'm just like, mind-blown."

(Photo by Dimitrios Kambouris/Getty Images for Sports Illustrated Swimsuit)

It was especially “cool” to get the news from Paris, Tiffany said, considering Paris' mom, Kathy Hilton, has been a big supporter of her modeling career ever since knowing of Tiffany's grandmother. "[Kathy] was encouraging me two years ago to walk in a Monse fashion show," Tiffany noted. "And then the next year, Monse hired me to be in a fashion show."

Read on for more of Tiffany Haddish's major career highlights.

OWN

First Major TV Series

In 2014, Haddish was cast as Jackie, a Burger Fast employee, in OWN's If Loving You Is Wrong.

First Major Film Role

Though she'd had bit parts in movies since 2005, in April 2016, she had a featured role in Keanu as Trina Parker (a.k.a. "Hi-C").

First Magazine Cover

Girls Trip stars Haddish, Regina Hall, Queen Latifah and Jada Pinkett Smith each got a solo cover for Essence's July 2017 issue.

Universal Pictures

First No. 1 Feature Film

In July 2017, Girls Trip topped the box office, grossing over $31 million in its opening weekend. It went on to earn $137 million worldwide.

Randy Holmes/ABC

First Time on Late-Night TV

On July 19, 2017, the actress appeared on Jimmy Kimmel Live! to promote Girls Trip—and share silly stores about Pinkett Smith.

Tidal

First Music Video

On Aug. 4, 2017, the actress starred in Jay-Z's Friends-inspired "Moonlight" video as Phoebe. Jerrod Carmichael played Ross, Lil Rel Howery played Joey, Issa Rae played Rachel, Lakeith Stanfield played Chandler and Tessa Thompson played Monica.

Showtime

First Showtime Special

On Aug. 18, 2017, the comedienne fulfilled a childhood dream when Tiffany Haddish: She Ready! From the Hood to Hollywood premiered.

Tiffany Haddish

First Time Presenting a Major Award

Joined by Pete Davidson at the 2017 MTV VMAs, Haddish announced Kendrick Lamar won Best Hip-Hop Video for "Humble."

Rosalind O'Connor/NBC

First Time Hosting SNL

Taylor Swift was the musical guest on the Nov. 11 episode.

Gallery Books

First Book Deal

The actress published her memoir, The Last Black Unicorn, on Dec. 5, 2017.

O'Keefe Reinhard & Paul

First Endorsement Deal

After sharing her hilarious Groupon story on talk shows, she became the official spokesperson for the brand and was featured in the Super Bowl ad in 2018.

imitrios Kambouris/Getty Images for The Business Of Fashion

First Fashion Week

With front row appearances at Tory Burch and Jeremy Scott's Spring/Summer 2019 presentations, the Night School actress made the most of NYFW in 2018.

Steve Granitz/WireImage