Harper Stewart (Taye Diggs) is a writer whose yet to be released debut novel is already creating waves in the literary world. While finding his stride professionally, he’s also at a crossroads romantically, with a long-time girlfriend named Robin (Sanaa Lathan) who is ready for marriage. But Harper puts everything on hold for one weekend to return to New York to be the best man in the wedding between his two closest friends, NFL running back Lance Sullivan (Morris Chestnut) and Mia Morgan (Monica Calhoun).
But his plans for a carefree weekend are jeopardized when he discovers Jordan (Nia Long), a college crush whom he almost slept with, got an advanced copy of his book. Things go from bad to worse when he learns the book has been passed around their close-knit group of friends. Normally this probably wouldn’t be a big deal, but the book happens to be not-so-fictitious accounts of things that happened to him in college, including a one night stand he had with the bride. The secret threatens to destroy everything Harper has worked so hard for, and he has to face a lot of hard truths in order to get his two best friends down the aisle.
I saw this movie when it premiered in theaters in 1999, and I loved it. It was funny, raunchy, and brutal with very little fluff that you usually find in a romantic comedy. Because of that, I bought it on DVD and took to watching it every now and then when the mood struck. Even now, 20 years later, I feel like it holds up as a romantic dramedy, even though my thoughts on the drama and outcome seem to have shifted slightly.
Every character has both likable and despicable traits that make them feel like fully realized people, except for maybe Shelby (Melissa DeSousa) who merely came across as a cookie-cutter version of a primadonna bitch. The dialogue is punchy and there is plenty of emotion and drama to deal with. So many rom-coms face criticism of not having enough conflict or dealing with misunderstandings that could have been solved with simple communication. If you want real conflict, The Best Man is the rom-com for you.
Everyone in this movie gives a strong performance, most notably Chestnut, who has to deal with the emotional toll of discovering his wife may not the angel he always thought her to be (while also being a total hypocrite, given the long list of women he has stepped out on her with since college), and Terrence Howard, who revels in his role as the snarky ladies man who is the only one to really call Harper out on his bullshit, and then gleefully watches on as Harper has to face his reckoning. Diggs strikes an impressive balance between wanting to be a successful writer and a good man, to just giving in to his “inner dog” and selfishly taking what he wants. Even Sanaa Lathan does a wonderful job with the limited screentime she actually receives. I would have loved to have seen more of her character, but I understood why she needed to be out of the picture for Harper to realize his mistakes, and what he truly wants for his future.
Malcolm D. Lee does an impressive job tackling the topics of morality, fidelity, and marriage without coming across as preachy, and I think his greatest success in the film is making you care about characters who are extremely flawed, and sometimes just downright horrible. Perhaps the ending falls prey to the typical Hollywood ending of a romantic comedy, and things may feel too easily resolved (thanks to the 2013 sequel, The Best Man Holiday, we discover that’s not exactly the case), but The Best Man is an entertaining dramedy that features a terrific ensemble, smooth direction, and a script that doesn’t sugarcoat the harsh realities of friendship and love.