It’s been over a decade since we saw the gang gather at Lance Sullivan’s massive estate, and honestly, the the best man holiday movie cast still feels like family. You know that feeling when you haven't seen your high school friends in years, but within five minutes of sitting down, you’re back to making the same jokes and picking the same fights? That is exactly the energy this group brought to the screen in 2013.
But making this sequel wasn't just some easy Hollywood paycheck. Far from it.
The road to getting the original 1999 crew back together for The Best Man Holiday was actually kinda messy. We’re talking about a 14-year gap between films. In Hollywood time, that’s an eternity. Most franchises would have rebooted with younger actors by then, but director Malcolm D. Lee knew he couldn't capture that lightning in a bottle without the specific chemistry of Taye Diggs, Nia Long, and Morris Chestnut.
Why the Best Man Holiday Movie Cast Almost Didn't Happen
Getting nine busy actors to align their schedules is a logistical nightmare. But the real kicker? The money.
Taye Diggs has been pretty vocal about this in recent years. He mentioned on a podcast that the cast was basically asked to do the sequel for "pennies" compared to their actual market value. He even used the word "disrespectful." It’s a wild thought when you realize how much money the first movie made, but apparently, the studio viewed it as a "cute little project" rather than the powerhouse franchise it actually was.
Despite the pay gripes, they all showed up. Why? Because they actually like each other.
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Sanaa Lathan recently told People that they are "beyond friends"—it’s a family dynamic. They have a group chat. They DM each other. When you see them onscreen, that laughter isn't always scripted.
The Heavy Hitters and Their Characters
If you need a refresher on who was who in this holiday tear-jerker, here’s the breakdown of the core players:
- Morris Chestnut as Lance Sullivan: The powerhouse running back for the New York Giants. Lance is the moral center of the group, but in this movie, he's dealing with the impending retirement from the NFL and, much more tragically, the health of his wife, Mia.
- Monica Calhoun as Mia Sullivan: The heart of the entire story. Monica’s performance is what turns this from a comedy into a full-blown "grab the tissues" event.
- Taye Diggs as Harper Stewart: Our narrator/writer who is struggling with a serious case of writer's block and a dwindling bank account.
- Sanaa Lathan as Robyn: Harper’s wife, who is very, very pregnant throughout the film.
- Nia Long as Jordan Armstrong: The high-powered MSNBC producer. She finally brings a boyfriend (Brian, played by Eddie Cibrian) to the mix, which creates its own set of "white boyfriend in a Black space" awkwardness.
- Terrence Howard as Quentin Spivey: The unfiltered, wildly successful brand manager. Honestly, Terrence Howard steals every scene he's in.
The Terrence Howard Factor
You can’t talk about the the best man holiday movie cast without mentioning Terrence Howard. He’s a bit of a wildcard, both on and off-screen. During the auditions for the first film, he reportedly brought his own guitar and started smoking a cigarette mid-scene. Taye Diggs was so annoyed he actually swatted the cigarette out of his mouth.
Instead of getting mad, Terrence laughed. That tension—that weird, competitive, but loving energy—is exactly what made the "Quentin" character work.
In The Best Man Holiday, he serves as the comedic relief, but he also has these deeply poignant moments where he’s the only one willing to say the truth. Whether he's talking about his "stimulus package" or checking Harper on his ego, Quentin is the glue that keeps the group from getting too "bougie."
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That Iconic Dance Sequence
Remember the "Can You Stand the Rain" New Edition tribute? That wasn't just a quick afternoon of filming.
The guys actually had to go through weeks of dance rehearsals. Sanaa Lathan joked that the men turned into "seven-year-olds" during practice. Taye Diggs, who has a Broadway background, was in his element. Morris Chestnut? Not so much. He reportedly had zero dance background and was terrified of looking stiff next to the others.
Malcolm D. Lee told them, "Be on your stuff because the girls are going to be watching." The pressure worked. It’s easily one of the most shared clips from the movie every December.
The Real-World Impact of the Cast
This wasn't just a movie about Christmas; it was a rare look at successful, middle-aged Black professionals navigating grief, career shifts, and faith.
When it hit theaters, it actually outperformed some massive blockbusters (including Thor: The Dark World) on its opening Friday. It proved that there was a massive, underserved audience hungry for these specific stories.
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The chemistry worked so well that it eventually led to the 2022 limited series, The Best Man: The Final Chapters. But for many fans, the 2013 holiday film remains the peak of the franchise because of how it balanced the extreme highs of the "Candy" reception dance with the extreme lows of Mia's storyline.
What Happened to the Cast After 2013?
Since the film's release, the careers of the the best man holiday movie cast have gone in wildly different directions.
- Regina Hall became a massive comedy mogul, starring in Girls Trip and hosting the Oscars.
- Terrence Howard went on to lead Empire as Lucious Lyon, though he's since claimed he’s "retiring" from acting to focus on his... unique theories about mathematics and "Terryology."
- Morris Chestnut basically found the fountain of youth and has stayed booked and busy in shows like The Resident and Our Kind of People.
- Harold Perrineau (who played Murch) moved on to lead the hit horror series From, proving he can do way more than just play the "submissive husband" role.
Actionable Insights for Fans
If you're planning a rewatch or just diving into the trivia, keep these points in mind:
- Look for the non-scripted moments: During the dinner table scenes, a lot of the crosstalk and "digs" were improvised by the cast because they've known each other since the late 90s.
- The soundtrack is key: Stanley Clarke’s score and the inclusion of artists like Anthony Hamilton and Marsha Ambrosius were intentional choices to bridge the gap between 90s R&B nostalgia and modern soul.
- Watch the background: In the "Can You Stand the Rain" scene, you can see the actresses' genuine reactions. They weren't just acting like they were impressed; they were actually surprised by how well the guys pulled off the choreography.
If you’re looking to catch up with the cast one last time, you should check out The Best Man: The Final Chapters on Peacock. It picks up a few years after the events of the holiday movie and finally gives some closure to the "will they/won't they" dynamic between Harper and Jordan. Just make sure you have the tissues ready again—this cast has a way of making you feel every single emotion.