This is a 1999 movie starring Taye Diggs, Nia Long, Morris Chestnut, and SanaaLathan. Up-and-coming author Harper Stewart (Taye Diggs) travels to UsefulNotes/LosAngeles for a wedding and is forced to deal with the fallout once his friends start to recognize themselves in his [[RomanAClef thinly-veiled autobiographical novel]]. A sequel titled ''The Best Man Holiday'' was released in 2013.
* BigManOnCampus: Lance, in the college flashbacks.
* CareerVersusMan: Jordan
* TheCasanova: Quentin
* EvilRedhead: Shelby
* ExpositoryHairstyleChange: used for the college flashbacks
* HenpeckedHusband: Julian
* HookerWithAHeartOfGold: "Candy"
* ImAManICantHelpIt: Quentin's philosophy
* MenDontCry: Averted by Lance [[spoiler: during his wedding ceremony]]
* MomentKiller: The skipping CD
* MyGirlIsNotASlut: Mia
* RomanAClef: Harper's novel.
* ReadyForLovemaking [[spoiler:Jordan]] and [[spoiler:Mia]], separately.
* RetroactiveRecognition: This is often considered to be Oscar nominee Terrence Howard's breakout role.
* ShirtlessScene: Harper
* SpearCounterpart: To black female-centered films like ''WaitingToExhale''
* [[spoiler:TheyDo: Lance and Mia]]
* ThoseTwoActors: Most of the principal actors have made at least one other film with one one of their castmates, but this film is the second of three turn-of-the-century romcoms that Sanaa Lathan and Taye Diggs appeared in together.
* UnresolvedSexualTension: Jordan and Harper