- Harsher in Hindsight: The sequel has a scene where the guys teasingly refer to Brian as "Robin Thicke", as they're both white men in love with African-American women. Not long after this movie's release, Thicke and his wife separated, and the divorce has been bitter, with allegations of abuse and infidelity.
- Retroactive Recognition: The first film is often considered to be Oscar nominee Terrence Howard's breakout role.
- Unintentionally Unsympathetic: Harper suffers this in both movies due to his writing career. In The Best Man, Lance finds out about his one-night college stand with Mia and lashes out at him over it(by lash out, we mean beat senseless and nearly toss off of a balcony) and for the rest of the film, Harper is portrayed as the only one in the wrong despite the fact that it was Lance's womanizing and unfaithfulness to Mia that led her to sleep with Harper out of revenge. In the second film, Harper genuinely tries to ask Lance's blessing before penning a biography about him but can't find a good time to sit him down and talk with him over it before Lance discovers a draft of the title cover on Mia's iPad and gives Harper an angry dressing down. The first thing Quentin asks Harper immediately after this (having missed the actual blowout and only seeing Lance pull out in a huff) is what has Harper done to Lance this time.
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