Film

The Best Man

Name: The Best Man
Genre: Drama, Comedy
Released: 1999
Cast: Taye Diggs, Morris Chestnut, Nia Long, Harold Perrineau, Terrence Howard

Other titles called The Best Man: the 1964 film, the 2023 film.

Comedy

A tight college friend group reunites for a wedding weekend, and the best man's new novel — a barely-disguised roman à clef about their tangled love lives — threatens to blow the whole thing up before the vows are said. Sharp, funny, occasionally soapy, and genuinely warm underneath the banter, it's the film that helped define the modern Black ensemble rom-com. Good for anyone who wants their comfort watch to still sting a little.

TMDb rating

3.3

Should you watch it?

Watch it if you like ensemble comedies about old friends who bicker, overshare and tell the truth at a wedding, with real heartache underneath the jokes.

Skip it if you want a lean, fast plot, since this one lingers on conversations and relationship talk, and the banter can feel more like a long hangout than a story.

What it asks of you: Two hours of talky, overlapping scenes, a crowd of characters to keep straight, and patience for the slow stretches between the laughs.

Not sure? Find tonight's pick in a minute.

If you liked this

Love Jones1997

Same stylish, literate, Black-professional world and the same easy charm — a writer and a photographer fall in love over poetry and jazz in Chicago. Warm, romantic, and quietly funny.

But It's a single couple's story rather than an ensemble, and the poetry-slam dialogue is very much of its moment.

Waiting to Exhale1995

The flip side — four women, not men, navigating love, betrayal, and friendship with the same mix of comedy and real heartbreak, anchored by terrific chemistry.

But Leans harder into melodrama and less into the banter-driven comedy the men's version leans on.

The Wood1999

Same year, same trick — three childhood friends stall a wedding while flashbacks unpack decades of loyalty, first love, and growing up together.

But Lower stakes and a smaller cast make it feel gentler and less starry by comparison.

Not sure tonight? Get a pick in a minute, starting from The Best Man

The wildcard

Something you would not have found on your own.

Husbands1970

Same core idea — three friends whose loyalty gets tested around marriage and mortality — but decades earlier, handheld, and stripped of every ounce of Hollywood polish.

Cassavetes strips away all the gloss and lets three lifelong friends binge, brawl, and confess their way across a boozy weekend after a funeral. Raw, funny, uncomfortable, and utterly real.

But Loose, improvisational, nearly two and a half hours with no tidy resolution — it demands patience rather than rewarding it easily.

Brown Sugar2002

Old friends, unresolved feelings, and a will-they-won't-they that unfolds against a hip-hop backdrop instead of a publishing deal. Effortlessly rewatchable.

But More straightforward rom-com than ensemble drama, with a fairly predictable arc.

The Big Chill1983

The blueprint for reunited-friends-airing-old-secrets movies — a funeral instead of a wedding, but the same bittersweet honesty about who you become versus who you were.

But The soundtrack, politics, and pacing are unmistakably early-'80s and can feel dated.

Four Weddings and a Funeral1994

A British cousin in spirit — a friend group orbiting a wedding, old flames colliding with bad timing, and jokes sharp enough to draw blood.

But Culturally a different world — posher, whiter, less about buried secrets than about missed timing.

Jumping the Broom2011

A modern wedding-weekend ensemble with a Black cast, class friction, and family secrets threatening to detonate the big day.

But Family conflict takes over from friend-group dynamics, and the comedy is broader, less introspective.

Something New2006

Same milieu of successful, funny, romantically frustrated Black professionals, with genuine chemistry between the leads and a sharp sense of humor.

But Centers on an interracial romance rather than a friend group's secrets — a different engine entirely.

Peter's Friends1992

An English country-house reunion where old university friends spend one weekend confessing everything they've been hiding, with the same mix of comedy and melancholy.

But Stagier and slower, with a very British, theatrical tone that won't be for everyone.

thirtysomething1987

Trades the single big reveal for years of slow-simmering secrets, showing what this friend group's dynamic looks like when it doesn't resolve in two hours.

The same close-knit friend group navigating marriage, ambition, and betrayal, but given a whole series instead of a wedding weekend — the stakes get room to actually breathe and change.

But Slow, talky, and unmistakably late-'80s in its style, soundtrack, and earnestness; a serious time investment for a niche mood.