Peter Sanderson (Steve Martin) is an uptight and workaholic tax lawyer whose wife Kate (Jean Smart) has left him and taken their two children, Sarah (Kimberly J. Brown) and Georgey (Angus T. Jones), with her. In his spare time, he develops an online relationship with Charlene (Queen Latifah) who calls herself "lawyer girl." But when they finally meet, she turns out to be a brassy and bold African-American who has escaped from prison and wants Peter to help her clear her name. Angered by her email deception that made him think she was a blonde bombshell, he tries to get rid of her. What he doesn't know is that he is dealing with a street-smart woman who is determined to prove her innocence no matter what it takes. She gets Peter's attention by holding a party at his house with all her black friends, which sends his nosy neighbor Mrs. Kline (Betty White) into apoplexy.
Meanwhile, Peter is trying to make a good impression on Mrs. Arness (Joan Plowright), a conservative prospective client with billions of dollars. He meets her at a lily-white country club, and when Charlene shows up, he passes her off as his children's nanny. Much to his surprise, Howie (Eugene Levy), another lawyer and co-worker, is smitten by Charlene and starts talking slang to prove how cool he is. She affectionately calls him "freak-boy." Kate's sister Ashley (Missi Pyle), a gold-digger who dates very rich old men, is also at the club that day. She takes an immediate disliking to Charlene, and they have a raucous catfight in the women's room.
Adam Shankman (The Wedding Planner) directs this film and makes the most of the considerable comic skills of Martin, Levy, and Queen Latifah. Charlene's energetic entry into Peter's stalled personal life enables him to get in touch with his playful and inventive self that has been buried away for years. She helps him draw closer to his teenage daughter and to see clearly how much he misses his wife. Peter in turn throws himself into the effort to prove her innocence, even going to a black downtown club where he tries to pass himself off as a homeboy.
The DVD has an audio commentary by director Adam Shankman and writer Jason Filardi, a behind-the-scenes featurette, and a short piece on Eugene Levy as "The Godfather of Hop." Perhaps the most fun is Queen Latifah's music video "Better than the Rest."