"There was a moment when we were shooting in a limo and Nia looked at me and said, 'You are a man now!'" recalled Chestnut with a chuckle during a recent interview. "We are in such different places in our lives and careers now. We're fortunate to still be here."
Chestnut, Long and the entire original cast of "The Best Man" — Taye Diggs, Terrence Howard, Sanaa Lathan, Harold Perrineau, Regina Hall, Monica Calhoun and Melissa De Sousa — return in the Christmas-themed "The Best Man Holiday," which is currently in theaters.
Although other follow-up films have come years after their originals — September's "Riddick," for example — the long-awaited "Best Man" reunion is a relatively rare feat, especially for a predominantly African-American cast.
"When the DVD market went down (in 2009), there were less and less urban movies getting made," said Chestnut of the lack of black ensemble films. "Tyler Perry was the only one really making (these) movies."
Lee, "The Best Man Holiday's" writer-director, struggled to get his sequel backed by a studio. The heartbreaking nature of the storyline, which was far from the jolly tale distributors were expecting, didn't help his cause.
Still, Universal Pictures went for the film, but only after the entire cast came to the studio for a reading.
"They understood what the movie was and what it could be," said Lee of the studio's response to the reading. "However, we know it's hard to get people to go see a film with a primarily black cast that doesn't star Will Smith or Denzel Washington."
When Chestnut portrayed Ricky Baker in 1991's "Boyz n the Hood," he became a talked-about young actor on the rise. After landing a few supporting parts in films like "The Inkwell" and "G.I. Jane," he won leading roles in "The Brothers" and "Two Can Play That Game" and was soon typecast as the heartthrob.
"At the time, I didn't realize I was doing all romantic comedies," said Chestnut. "But I'd go to set and not really respect what I was doing. I didn't see it as a challenge. It was like, 'Go sit there and kiss Vivica Fox. Go sit there and joke with Gabrielle Union.'"
Though he became a household name among African-Americans, Chestnut didn't have the box office draw of a Smith or Washington.
"I woke up one day and was like, 'OK, I had fun, but I didn't really fit anything meaningful in there," Chestnut said. "It was a lesson learned."
He's since appeared in films like "Think Like a Man," ''Identity Thief" and "Ladder 49," and on TV shows such as "V," ''American Horror Story" and "Nurse Jackie." But he still fights for roles.
"It's a never-ending story," said Chestnut, who admires the talent of "Best Man" co-star Howard.
"He's a different cat," Chestnut said of the Oscar-nominated actor. "We call Terrence the beautiful mind because sometimes a person can be so brilliant that it is hard for them to stay focused. ... When you say 'action' he is so phenomenally present, but when you say 'cut,' he is phenomenally detached."
As Lance, the devoted football star in "The Best Man Holiday," Chestnut "had to have his poker face on and cracks in the armor," said Lee. "He played all of that beautifully. He was extremely serious."
Yet he couldn't evade his hunky habits. The 44-year-old, who lost 30 pounds for the part, goes shirtless in the film.
"We didn't shoot that scene until the second to last week of production!" said Chestnut. "Maintaining a diet and exercise routine at my age is a lot. I couldn't cheat."
But it was all in a day's work. "This movie was fun and emotional," said Chestnut. "To be able to go deep into this character and see my development as an actor at this stage in my career — 20 years in — I'm very fortunate for that."