The Best Man: The Classic Black Romantic Comedy Gets Its Flowers and Its Ending

The Best Man Movie

You’ve probably heard the ’90s were a great time for black television. Relatively speaking, it was probably peak black TV, as there were 15 sitcoms at the decade’s height in 1997, at a time when there were just a handful of broadcast channels that mattered. But while TV was certainly a more welcoming place to black people during that era, it also gave birth to some of the best black romantic comedies of all time. Chief among them: The Best Man (1999). 

The Best Man was stacked, too. If you want to talk about talent, Black acting talent, in particular, they had it all. Taye Diggs, Nia Long, Morris Chestnut, Terrence Howard, Regina Hall and Sanaa Lathan…are you kidding me? All of those names would go on STAR in movies! And yet, this film was able to get them all on one set for a budget reported to be just $9 million. Even 20 years ago, that’s a steal for this kind of acting talent. Unfortunately, the flipside of that is that you could only get away with that kind of thievery with a Black movie, as we’ve routinely been underpaid as a result of discrimination against Black people in Hollywood from the institution’s very inception. And I didn’t mean to leave off amazing actors like Harold Perrineau, Monica Calhoun, or Melissa De Sousa, who were just terrific and made this simple little film about old college friends getting together something magical. 

So as we get set for the television debut of The Best Man: The Final Chapters, which premieres on Thursday, December 22, 2022, I thought we’d take some time to give the original movie its flowers. It’s a movie that just doesn’t get enough credit for the writing, the acting, the characters, and the way it movie made so many people feel during a time in America when Black upward mobility was on the rise and we were feeling more powerful than ever before–and perhaps ever since! 

Let’s give them their flowers by focusing on the actors. Taye Diggs as Harper Stewart was fantastic. In playing a character that was both bookish and cool, Diggs hit it out of the park, leveraging every emotion known to mankind as he got beat up, slapped around, seduced, berated, and humbled many times throughout the movie. That type of range is why he has gone on to have the standout career he has had.

Then take Nia Long, for whom I’m not even sure how in the world they were able to afford her. This type of bargain, or better yet, theft, is the type of thing that almost exclusively happens to black women, because if a white actress had hitters in their bag like Boyz n the Hood, Made in America, Friday, Love Jones, Fresh Prince of Bel-Air, and Soul Food, before she starred in the The Best Man, there’s no f’ing way she could have been employed on a $9 million budget movie. The more I think about it, this is the actress free agent signing of a lifetime! To have that many gems in your filmography before the age of 30, not to mention having been just about the only Fresh Prince guest actress to stick around for more than 2 episodes, is unparalleled. Like I really can’t think of anyone that put in that kind of work, when it comes to classic movies that we talk about all the time, and yet she was fewer than 10 years into her film acting career! Obviously, she crushed it as Jordan Armstrong (what an incredible name!) in The Best Man, playing a super serious TV executive and woman-looking-to-sew-an-oat at the same damn time. 

Of course there was the now infamous, Terrance Howard. He too was barely 30 by the time this movie dropped. He didn’t have the classic Black movie filmography Nia had, but he was no slouch with The Players Club smack in the middle of his IMDb. In what was probably the breakout role of his career, it’s easy to see how Terrance went from playing Quentin Spivey on The Best Man to many of the roles he’s played since in projects like Ray, Hustle & Flow, Get Rich or Die Trying, and of course, Empire. He is always playing the cool guy that borders on dickhead. He threads that needle so well that it makes you wonder why he’s so good at it–or maybe you don’t have to wonder

If Nia Long was already a bona fide star by this point, then Morris Chestnut was hot on her heels. He debuted in Boyz n the Hood–yes, you read that correctly! Hist brilliant performance in Boyz in the Hood was his first gig! That’s pure talent when you can come out the gates like that. Morris would then star in movies like The Last Boy Scout, Higher Learning and G.I. Jane. With the rough and tough exterior of most of the roles he played, playing the football player, with a touch of poet, was easy money for him in The Best Man

And last, but not least, perhaps my favorite (and most successful?) of the bunch is Sanaa Lathan. Lathan was very much a supporting actress in this one (she would go on to have a much more prominent role in the sequel), but the talent still shined through. Like the other super accomplished actors, she came in with her bona fides as well. On television, she had already guest-starred on In the House, Moesha, Family Matters and NYPD Blue. In film, she hadn’t really had that starring role of note yet. Oddly enough, she shot The Wood, Life and Catfish in Black Bean Sauce, all around the same time she shot The Best Man, so Sanaa had four movies drop in 1999. Other Black film historians of different walks might say The Wood was her better outing, but I fervently disagree. Her unique role as the “new girl”, Black, chef, fiancee-to-be in The Best Man, and her chemistry with Diggs, were so good that they would quickly go on to film Brown Sugar together just to exploit that seeming on-set magic.

So, yes, the acting was great. Those actors, hopefully, have gotten their flowers many times over, but it doesn’t hurt to do it once more. 

But let’s now turn to the writing and story behind this great film. Now, it’s almost hard to imagine, but the same director who gave us a movie like Roll Bounce is also the guy who wrote The Best Man–Malcom Lee. This was his debut film, and to his credit, he delivered on the artistic promise of the Lee family (of which Spike Lee is the most notable, and is also probably the reason this movie got made). The plot of The Best Man, seemingly simple, was full of surprises, turns, deceits, betrayals, flashbacks, nostalgia, craziness, music, and even sports. The movie gives us the tale of a writer on the brink of stardom with his upcoming book, but unbeknownst to his closest friends, his book is actually a story about his past. With his best friend, who is actually the persona behind one of his book’s main characters, about to get married, the writer’s inner-circle reunites. The writer, Harper (Diggs), is simply trying to get through the wedding without having his inner-circle notice what his book really entails, all the while, he tries to sew a wild oat from college with the one that got away, Jordan. But of course, Harper already has a girlfriend, so that whole sewing of the oats part is frowned upon, and the former is, as expected, a failure.

The film does a great job of making us think Harper might get away with the sultry details contained in his book, and the description of the crew’s college days is well done in a short amount of time. I won’t go too much more into detail, because if you know, you know, and if you don’t, you sho ‘nough need to go watch this movie ASAP. I promise, given the relatively few number of Black films being made (and because BlackOakTV isn’t in the feature film game…yet), you will be hard-pressed to find a better Black movie on any of your favorite streaming platforms! 

While the writing was great, the actors were classic, and the actresses were even more phenomenal, this movie is most noted for being nostalgic across generations and across time. If you watched The Best Man in 1999 when it came out, it harkened back to the early 90s, when things were a little simpler, technology hadn’t started to intrude on our lives, and the paparazzi was a thing, but less of one. At the same time, the movie also takes you back to your college or early adult days, and made you nostalgic about all of the wonderful people in your life then. And if you fast forward to today, not only does the film make you feel for your college days, or the early 90’s, but it also makes you reminiscent of the movies actual period during the late 90s, when Black people, in particular, were coming off a socioeconomically good decade, seemingly headed for nothing but more and more growth as a people. We were thriving. Or at least, so it seemed!

So shout out to The Best Man, which I hope considers this just some of the flowers they deserve. Its reception in 1999 certainly deserved better than history describes it. This cast was unparalleled, and the story was both compelling and an important timestamp on a great time in African-American culture. While the NAACP Image Awards showed the entire cast some nomination love, and the movie won Outstanding Motion Picture, Hollywood didn’t give the film its true due. Clearly, the movie deserved more respect, which is why it came back strong with the sequel, The Best Man Holiday, and why the third installment, The Best Man: The Final Chapters is coming to a SmartTV screen near you–and despite its title, I bet it will be another Black TV show you can invest in.

But if you haven’t seen the original movie, go see it now. And if you’ve already seen it, watch it one more time for nostalgia’s sake. Because you deserve some flowers, too!

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