There are great actors, and then there are icons who have become ingrained in the culture. Morris Chestnut’s rise in the 1990s, starting with his breakout role in the cultural landmark Boyz n the Hood — in which he was only about 22 years old — made him a defining face of Black Hollywood.
Chestnut’s career continued in TV shows like “Living Single,” “American Horror Story,” “Nurse Jackie,” “Rosewood,” “The Resident,” “Reasonable Doubt,” and “Watson,” where he served as the title character and executive producer. On the film side, he also starred in some Black love favorites like Two Can Play That Game, Breakin' All the Rules, Think Like a Man, and Girls Trip. He is also a pivotal piece of the iconic franchise that started with 1999’s The Best Man. The film continued to have such relevance that it spawned The Best Man Holiday in 2013 and “The Best Man: The Final Chapters” in 2022.
While he is known for being an extremely handsome man, his talent as an actor made it clear that his spot on the big screen was well-earned. In 2022, he was even awarded a star on the Hollywood Walk of Fame. In honor of his decades-long career, resonance with audiences, and standing in Black culture, take a look back at where he started with these nostalgic throwback pictures.
1. Boyz n the Hood premiere
We might know them on paper as Morris Chestnut and Cuba Gooding Jr., but our hearts know them as Ricky and Tre. They’re pictured here at a premiere party for Boyz n the Hood in July 1991.
2. Celebrity baseball game
In 1992, he joined Pamela Anderson, Jason Bateman, Tom Selleck, and more for the Hollywood All-Stars Baseball Game at Dodger Stadium. We aren’t sure who won, but it was a fun sports-meets-Hollywood crossover event.
3. "Out All Night" premiere party
Chestnut, Patti LaBelle, and Duane Martin all starred in “Out All Night” and showed each other some love at a premiere event in Hollywood. The series ran from 1992 to 1993 and was set in the same universe as "The Fresh Prince of Bel-Air."
4. MTV Rock N' Jock B-Ball
In September 1992, the “Legends” actor participated in the MTV Rock 'n' Jock B-Ball, a charity event for organizations like the Pediatric AIDS Foundation, where celebrities played basketball with professional athletes. It was also a TV series that aired on MTV and featured multiple sports.
5. G.I. Jane premiere
The actor/producer married Pam Byse in 1995, so naturally, she has been his date to countless premieres. Here’s a picture of them at the G.I. Jane premiere when they were only two years into their decades-long marriage.
6. BET Awards press conference
Photos like this capture incredible moments in time for the culture. At this nominations press conference for the 2nd Annual BET Awards, he snapped this picture with Bow Wow, Cedric The Entertainer, Ashanti, Ja Rule, and Steve Harvey.
7. Like Mike promotion event
Chestnut and Bow Wow starred in the 2002 classic, Like Mike. They’re pictured here at Planet Hollywood Times Square in NY, promoting the film and signing jerseys.
8. Celebrity charity poker tournament
In May 2005, GQ and Calvin Klein hosted their 2nd Annual Celebrity Charity Poker Tournament in Beverly Hills. The “All American” actor participated in this game with fellow actors Nicholas Gonzalez and Laura Prepon.
9. The Game Plan premiere
We hope they know how cool their dad is. For the premiere of The Game Plan in September 2007, he brought his wife and their children, Grant and Paige.
10. Salvation Army event
In early December 2007, the stars of The Perfect Holiday, including Chestnut, Queen Latifah, Gabrielle Union-Wade, and Faizon Love, gathered together to give back. They hosted a Salvation Army event for kids in need in Atlanta.
11. BET Awards
At the 2008 BET Awards, they called on three of the culture’s favorites. He joined Cuba Gooding Jr. and Nia Long on stage to present the award for Best Female Hip Hop Artist, which went to Missy Elliott.
From participating in charity events to the stages of the BET Awards, Morris Chestnut’s ‘90s and 2000s era was more than a moment. These throwback photos remind us why his legacy still resonates today.