6) Brown Sugar (2002)
Director: Rick Famuyiwa
Starring: Taye Diggs, Sanaa Lathan, Boris Kudjoe, Queen Latifah, Mos Def
A beautiful cast is punctuated by the classic story of friends who get a little too close for comfort. Though it’s a story we see played out in movies over and over again, what makes Brown Sugar stand out is that it pretty much had one of the coolest soundtracks of all time, and the ultimate hip hop love song, “Love of My Life” by Erykah Badu and Common.
5) The Best Man (1999)
Director: Malcolm D. Lee
Starring: Taye Diggs, Nia Long, Morris Chestnut, Terrence Howard, Sanaa Lathan
If you watch the trailer, you basically have seen the whole movie, but it doesn’t make it any less good. The Best Man gets point not for its originality but for it’s polished sameness. One of those films that every time its on, no matter what part it’s at, we watch until the end and no other film on this list has that kind of staying power.