The Apprentice (1999)

Joe Landon comes home from work to discover that he is no longer welcome. Tossed from the nest, Joe moves on to build a new life in the city. Teaming up with Scott Matthews for play for pay, Joe then meets Chris Rock, who teaches him the ropes on how to succeed in the world of high-class male hustling. The two instantly hit it off and proceed to cross the line between work, sex, and love.