Monica Calhoun, Morris Chestnut, and Taye Diggs in The Best Man (1999)
Monica Calhoun, Morris Chestnut, and Taye Diggs in The Best Man (1999) [Credit: imDB]

The Best Man (1999) film review & summary, Where to watch

Title: The Best Man (1999)
Director: Malcolm D. Lee
Duration: 2hrs
Cast: Taye Diggs, Morris Chestnut, Nia Long, Terrence Howard, Sanaa Lathan, Harold Perrineau

The 90s were interesting times for black films because after a lot of experiments, a lot of segregation, and a lot of backlash from studios, black people were finally able to make signal movies that resonated with a predominantly black audience. After the Spike Lee saga to make the Malcolm X biopic in the early 90s, it was clear that films by black filmmakers were going to reach a new peak and that peak came shortly after, towards the end of the 1990s. The Best Man was right in the middle of that peak.

Not only is it one of the most intriguing romantic dramas on the big screen in the 90s, but The Best Man has also aged exceptionally well and is considered a classic by anyone who knows their onions. This is not even a critic thing; it’s a black thing. While you don’t necessarily have to be back to enjoy this movie, there are just some elements that cannot be properly appreciated by non-Black people. In other words, it’s not a Tyler Perry movie (no disrespect to Perry in any way). Actually, it is the kind of movie that foreshadowed the kinds of movies Perry made in the mid-2000’s like Why Did I Get Married. A film with multiple main characters, all friends, and enough drama for a soap opera.

The Best Man follows a group of friends, two of whom are getting married to each other. The titular best man, Harper Stewart (Taye Diggs) is a writer who is about to publish a book based on the lives of he and some of his friends, who have now gathered together for a wedding. But when an early exclusive copy of his book finds its way into the hands of the groom-to-be, all hell is bound to break loose because the best man has enough juicy stories from the past in it and it didn’t take long for the groom to put two and two together.

Now there is trouble in paradise as the groom who feels betrayed calls off the wedding and to get him to proceed as planned, it has to be an all-hands-on-deck thing. Meanwhile, there are other juicy subplots like the engaged best man who’s presented with a once-in-a-lifetime opportunity to hook up with one of his best friends, Jordan (Nia Long) whom he’s always admired. Then there’s the friend who’s going through hell at the hands of his girlfriend and needs a way out before she takes his life.

The cast is an ensemble that includes some of the best actors around at the time. There’s Taye Diggs who starred in The Wood in 93, Morris Chestnut who was in Boyz N The Hood in 95, Nia Long from Friday & Boyz N The Hood, and Terrence Howard, who later became widely known for his role in the TV series, Empire. Together, they all delivered what is perhaps the best-ever romantic drama with an all-black cast.

Directed by Malcolm D. Lee, The Best Man was a huge success grossing $34.5m on a $9m budget.

Rotten Tomatoes: 72%
Letterboxd: 3.3/5
IMDb: 6.7/10

Where to Watch Do the Right Thing (1989)?

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