From Boyz to Best Man: Morris Chestnut looks back at his career

Morris Chestnut Role Call

For nearly 30 years, Morris Chestnut (starring in the upcoming NBC series The Enemy Within) has been a mainstay of the silver screen, portraying a range of players (on the field and off), best friends, boyfriends, and everything in between. The actor—whose swoon-worthy smile has made a rom-com classic—walked us through a few of his favorite roles.

Boyz n the Hood (1991)

Chestnut’s first role was as young Ricky Baker in the 1991 teen drama, alongside Cuba Gooding Jr. and Laurence Fishburne. “It was a very fun, enlightening experience for me,” Morris says. “It really taught me a lot. I was on set learning from Cuba, who was a veteran at the time. Watching him work, and watching Fishburne—it was a very, very new experience and I was just trying to absorb everything. It felt like everything was traveling at warp speed.”

The Best Man (1999)

In the classic wedding ensemble rom-com, Chestnut played the groom, Lance, whose best friend (Taye Diggs) had slept with his bride-to-be.

"It was a great experience. It was my first time in New York Ctiy filming. I had only been to New York for no more than a day or two, and it was really my first time being in New York and working in New York. The first Best Man is one of my all-time favorite experiences on a set. Just the camaraderie, chemistry, being in New York—I just have so many great memories from that production.”

His character was a running back with the New York Giants, and while he never went pro, Chestnut shares a love of football. “I played in high school. I wasn’t a running back, but this is true: I loved football more than I loved girls at one point.”

Two Can Play That Game (2001)

In this rom-com, starring Vivica A. Fox, Chestnut plays a playboy attorney named Keith who can’t commit. “Two Can Play That Game was hilarious because working with Vivica and Gabrielle and then at the end, with Anthony Anderson, those are just three extremely talented people who are still working to this day. That was just another experience where we had a lot of fun on set.

Breakin' All the Rules (2004)

Over the course of his filmmography, Chestnut has worked with Gabrielle Union four times, starting with 2001’s The Brothers. “Gabrielle is an actor’s actor. An incredibly smart person, witty. She just has this great personality. Just fun, and fun to be around."

The Perfect Holiday (2007)

“It’s funny,” Chestnut says. “Every time that I work with Gabrielle, years can pass and we don’t talk that often, but as soon as we get back in front of a camera together, it’s like riding a bike. It’s a great experience working with her."

The Best Man Holiday (2003)

Lance, Harper, Robyn, and the entire gang all came back together 14 years after the original film came out. In both films, his character Lance was forced to deal with major emotional moments. “In Best Man Holiday, there was a scene at the cemetery where they were dropping her body down, I just had to isolate myself because everyone’s having fun, talking, and I had to be in this emotional state. But it was incredible reuniting with everyone. I do love that character. In the sequel, the character was going through a lot of emotional turmoil. In the third one, I’m going to get to have some fun.”

Think Like A Man (2012)

Chestnut has a cameo in the rom-com based on the Steve Harvey book, playing Lauren’s (Taraji P. Henson) caddish ex. “It was a cameo role, however a lot of people felt that my character was a little too sure of himself—to put it in nice terms. I think one of my least-liked characters."