Honestly, if you grew up in the early 2000s, you probably thought you knew everything about dating because of Shanté Smith. Two Can Play That Game actors didn't just deliver a rom-com; they basically handed out a tactical manual for psychological warfare in relationships.
It’s been over twenty years since Vivica A. Fox broke the fourth wall to tell us how to "tame" a man. Looking back, the cast wasn't just a group of rising stars. It was a certified Black Hollywood Avengers lineup. You had the king of the "dream guy" roles, the queen of the 90s action-romance crossover, and a supporting cast that eventually snatched Oscars and dominated primetime TV.
But here’s the thing. People usually remember the "Ten Day Plan" and the sleek suits. They forget how stacked this roster actually was.
The Power Players: Vivica A. Fox and Morris Chestnut
Let's talk about the chemistry. It was electric. Vivica A. Fox was coming off huge hits like Independence Day and Soul Food. In this film, she wasn't just the lead; she was the narrator of our lives. Her character, Shanté, was an advertising exec who treated love like a brand campaign. Vivica played it with this sharp, sophisticated edge that made you believe she really could control every man in the room with a flick of her hair.
Then there’s Morris Chestnut.
Seriously, was anyone doing it like Morris in 2001? He played Keith Fenton, the smooth lawyer who gets caught "stepping out" with a coworker. Morris has this specific brand of charm where he can look guilty and completely innocent at the same time. He wasn't just the foil to Shanté’s games; he was the one proving that the "rules" don't always work when actual feelings are involved.
They weren't just actors reading lines. They were icons of an era where Black romantic comedies were finally getting the high-gloss, high-budget treatment they deserved.
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The Supporting Cast That Changed Everything
If you haven't rewatched this lately, you might have forgotten that Gabrielle Union was the "villain." Well, sort of. She played Conny Spalding, the rival who tries to swoop in on Keith. This was right around her Bring It On fame. Gabrielle brought a level of "mean girl" energy that was so polished it was almost scary.
And then there's the comedy relief that actually had teeth:
- Anthony Anderson: He played Tony, Keith’s best friend. Tony was basically the anti-Shanté. He was the one in Keith’s ear telling him how to counter-play the games. Anthony’s career exploded after this, moving from the "funny best friend" to leading major franchises like Black-ish.
- Mo'Nique: Before she was winning an Academy Award for Precious, she was Diedre. She was loud, unfiltered, and provided the perfect reality check to Shanté’s overly-manicured life.
- Wendy Raquel Robinson and Tamala Jones: They played the friends, Karen and Tracey. While they might seem like standard archetypes, their performances gave the movie its "brunch with the girls" vibe that made the whole story feel lived-in.
Even Bobby Brown showed up! He played Michael, and honestly, his presence alone cemented the movie's place in the 2000s pop culture hall of fame.
Why the Movie Still Hits Different in 2026
We live in an era of "dating apps" and "situationships" now. The games Shanté played in 2001—ignoring phone calls for 24 hours or making a man "earn" a date—seem almost quaint compared to ghosting and breadcrumbing.
However, the Two Can Play That Game actors managed to tap into something universal. It wasn't really about the specific rules. It was about the fear of being vulnerable. We watch Shanté struggle because she’s terrified of losing control. We watch Keith push back because he wants to be respected.
The movie was criticized by some for being "too glamorous." Critics at the time, like those at Exclaim!, argued it looked like a 90-minute music video. But for the audience? That was the point. Seeing Black professionals in fancy cars, with high-powered careers, dealing with "rich people problems" was aspirational. It was a vibe.
The Career Trajectories
Looking at where they are now is wild.
- Vivica A. Fox became a producing powerhouse and a staple in the Lifetime movie universe.
- Gabrielle Union is basically a mogul at this point, with books, hair care lines, and a massive production company.
- Anthony Anderson became one of the most recognizable faces on television.
- Mo'Nique proved she was one of the greatest dramatic actresses of a generation.
What You Should Actually Do Next
If you’re looking to dive back into this world, don't just stop at the credits. There are a few ways to really appreciate what this cast did for the genre.
First, go back and watch the "counter-sequel" or spiritual successor, Three Can Play That Game. It’s a 2007 follow-up where Vivica returns as Shanté, but this time she’s a professional relationship expert helping a new client. It’s not quite the original, but Vivica’s performance is still top-tier.
Second, check out the stage play adaptation. Producer Je'Caryous Johnson actually brought the story to the stage a few years back, and Vivica A. Fox reprised her role. It shows just how much staying power this character has.
Finally, if you’re a fan of this specific cast, look for the "unofficial" trilogy of that era: The Best Man, The Brothers, and Two Can Play That Game. These three films featured many of the same actors and defined the "Black professional rom-com" aesthetic of the early millennium.
The reality is, the "game" hasn't changed. Only the players have.
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Next Steps for You:
- Stream the Original: It's frequently available on platforms like Hulu or BET+.
- Watch "The Best Man" (1999): To see Morris Chestnut in another career-defining role.
- Follow the Cast on Socials: Most of these actors, especially Vivica and Gabrielle, are very active and often share "throwback" content from the set.