Compared to some of his costars, Chestnut had a nice-size résumé before he graced the big screen as the smooth playboy/womanizer Lance Sullivan. His credits included stints on shows like "Out All Night" and "Living Single," a couple of TV movies, and 1994's "The Inkwell," which starred heavy hitters like Tate, Glynn Turman, Jada Pinkett Smith, and Joe Morton. However, Chestnut's biggest role at the time was, without a doubt, Ricky in "Boyz n the Hood."