The Best Movies Like The Best Man

If you haven’t seen Malcolm D. Lee’s The Best Man, we recommend you seek it out. As befits the cousin of Spike Lee, The Best Man is an affable, well-crafted look at love in the African-American community, and it holds up well considering it’s twenty-two years old. Of course, if you love it like we do, there’s a good chance you’ve exhausted The Best Man and can quote every line as if you wrote the script. If that’s the case, you’re probably looking for more movies like The Best Man so that you can expand your horizons a little. We’ve got you covered. Here are some of our favourite movies that we think you’ll love if you’re a fan of The Best Man.

The Best Man Holiday (2013, dir. Malcolm D. Lee)

What better way to begin a list of movies like The Best Man than with a direct sequel? Lee once again examines African-American life through a lens of romance and dramatic tension, and The Best Man Holiday proves the first movie wasn’t a one-hit wonder. Sure, the script isn’t particularly creative or original, and the premise will be familiar to you if you’ve seen any reunion drama ever, but this Christmas-themed followup to The Best Man still gets us. Morris Chestnut, Taye Diggs, and the gang are in excellent form just as they were in the first movie, and even though we know it has flaws, The Best Man Holiday is on hard rotation for us at Christmas.

Two Can Play That Game (2001, dir. Mark Brown)

One look at the poster for Two Can Play That Game should tell you everything you need to know about this one. It’s creaky in places and suffers from an overly formulaic setup and script, but Two Can Play That Game still stars Vivica Fox and Morris Chestnut at the top of their respective games. They play a couple in the midst of a relationship crisis, although the movie is much more fun than that implies. There are plenty of crossed wires and misunderstandings to get your head around, and the fact that the whole thing ends exactly as you expect it to doesn’t feel as frustrating as it should. Two Can Play That Game coasts on charisma alone, but it’s fun.

Brown Sugar (2002, dir. Rick Famuyiwa)

Taye Diggs makes another appearance in this hip-hop rom-com. Sanaa Lathan plays Sidney, a woman who’s just been appointed as the editor of hip-hop bible XXL, and Diggs is her childhood sweetheart. This rom-com is so formulaic there’s even a dramatic scene set in a train station, but again, the charisma of Diggs, Lathan, and fellow stars Queen Latifah and Mos Def make this one shine. Sadly, the filmmakers appear to have missed a trick by not including the D’Angelo classic of the same name, but the soundtrack is appropriately cool and features luminaries like Erykah Badu, Common, The Roots, and Mary J. Blige. An essential watch for any fan of hip-hop and R&B.

How Stella Got Her Groove Back (1998, dir. Kevin Rodney Sullivan)

It seems like all the best movies like The Best Man star Taye Diggs, doesn’t it? Here, Diggs is the wonderfully-named Winston Shakespeare, who’s pursuing our heroine, played by Angela Bassett. The titular Stella decides she needs a break from her hectic life as a stockbroker, and that break can be found in Jamaica, where she meets Diggs and her life changes forever. Delightfully, Stella also stars Whoopi Goldberg, whose presence denotes a good time even if it doesn’t necessarily signal a great movie. Indeed, Stella is somewhat cliched, but the performances are so watchable and the scenery so beautiful that you’re swept up anyway.

Soul Food (1997, dir. George Tillman Jr.)

Another The Best Man luminary makes an appearance here, namely Vivica A. Fox, who’s playing the younger sister of the Joseph family. Soul Food is all about the trials and tribulations this family goes through and whether or not they’ll be able to maintain their close-knit connections through the most difficult moments in their lives. Soul Food received acclaim for showing a different side to African-American life; many movies glamourised the violence and hatred that (in a rather racist fashion) permeated perceptions of Black culture at that time, but Soul Food showed that Black families could be portrayed in a positive light, too. It also made its way to TV!

Breakin’ All The Rules (2004, dir. Daniel Taplitz)

Another rom-com with a scene of breathless declaration involving a train or train station, Breakin’ All The Rules certainly isn’t going to win any awards for originality. That’s not likely to be a problem, though, as it offers warm, comforting fare of an autumn or winter’s evening. Jamie Foxx is the jilted Quincy Watson, who may or may not find love elsewhere as the movie progresses (spoiler: he does). Again, The Best Man shows its influence over popular culture, as Morris Chestnut appears as Quincy’s cousin Evan. You may have some trouble following the plot, which certainly zigzags and shifts a lot more than it needs to, but if you just focus on the emotional core of the movie, you’ll likely have a much better time.


These are our favourite movies like The Best Man. Bear in mind some of these movies aren’t actually “like” Malcolm D. Lee’s movie in terms of content; it’s more that we feel they’ll appeal to fans of that movie thanks to their complementary styles or adjacent subject matter. Which ones did we miss?

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