American Milkshake

In the mid-90's, Jolie Jolson, a white high school student (the great-grandson of blackface performer Al Jolson) wants to be on the basketball team because he thinks that it will bring him closer to being the one thing that he isn't: black. His African American girlfriend, Henrietta, is pregnant with another man's baby and had a seedy past which includes appearing in a sex tape. Jolie gets on the basketball team due to a large donation from his well-off father, and ends up dating one of the cheerleaders for the team, and accidentally impregnates her.