Why The Best Man Remains a Classic:Loyalty, Love, and Morris Chestnut

Hey Candi Crew!

Welcome back to Part 2 of our ’90s Black Rom-Com Rewind! After getting nostalgic with Love Jones, we’re diving into another fan-favorite: The Best Man (1999), directed by Malcolm D. Lee. This film follows Harper Stewart (Taye Diggs), who attends his best friend Lance’s (Morris Chestnut) wedding—but with several twists & turns. Harper’s recent “fictional” book exposes a college affair that hits a little too close to home, leaving his

friends to connect the dots and stirring up wedding-weekend drama.

As we dig into this story of love, ambition, and loyalty, get ready for some grown-woman reflections on the drama, charm, and messy friendships that make The Best Man a classic

and still one of my top 10 favorite films.

The Charm and Chaos of The Best Man

Get ready for ALL spoiler alerts!!

Once the plot unfolds, it’s clear Harper isn’t just a flawed character—in my opinion he’s the story’s true villain.

Betraying his best friend Lance by sleeping with his girlfriend Mia, then "confessing" it in a “fictional” book? That’s a toxic mix of ambition and poor judgment. Meanwhile, Lance is ready to move past his wild college days and commit, which makes Harper’s disloyalty and action to write about it sting even more. And Mia, girl…seeking revenge by hooking up with Lance’s best friend? That’s a level of petty that I wouldn't even touch. And those that know me, know that I can be petty!

One thing I couldn’t help but notice while rewatching The Best Man is the recurring theme of messy friendships— just like in Love Jones. Apparently, in the ‘90s, dating a friend’s ex or their close friend was a whole thing! Harper’s betrayal of Lance by sleeping with Mia and then airing it out in his book gives

us another dose of questionable ‘90s “friend ethics.” Maybe morals and values have always been a bit selective.

Thinking back to Love Jones, it’s interesting how the ’90s had this subtle theme of dating within the friend group. Apparently, crossing those lines was a trend, and people’s morals and values have always been a little selective!

Ultimately, The Best Man is more than just a messy tale of love and betrayal. It’s about growth—especially when it comes to Lance Sullivan, played by the oh so fine Morris Chestnut. Sure, Lance had his flaws in college, but his character’s evolution into a man ready to commit to his soulmate is heartwarming. What I love most about this film is the way it showcases Black characters in professional settings. All the characters are college-educated and carving out their careers, far removed from the negative stereotypes of drug dealers and gangbangers. At the time, I was entering my freshman year of high school, starting to think about college

and life after. Seeing these characters succeed in real-world roles made it feel like there were endless possibilities for me, too. And let’s be real, can we ever stay mad at Morris Chestnut? I’m still in “forgiving” mode when it comes to him!

The film’s exploration of love, ambition, and friendship hits different as we see the characters navigate life’s ups and downs. The Best Man remains a classic that continues to resonate, reminding us that true friendship and loyalty are things worth fighting for. While The Best Man stands strong on its own, the sequel, The Best Man Holiday, continues the journey with a more emotional and grown-up storyline. And if you’re not ready to say goodbye to these characters, the Best Man series picks up with them over 20 years later, giving us a deeper look into their lives and relationships. It’s a must-watch for anyone who’s loved these characters and is curious about how they’ve evolved.