Peter Sanderson (Steve Martin) is a workaholic tax attorney corresponding with an online friend known only as "lawyer-girl." On their first blind date, Peter learns that "lawyer-girl" is Charlene Morton (Queen Latifah), a plus-sized, wrongfully convicted bank robber claiming her innocence who wants Peter's help in getting the charges dropped. Peter also must deal with Virginia Arness (Joan Plowright), an eccentric billionaire, to bring her business to his firm, as well as competitive colleagues and bosses. His neighbor, Mrs. Kline (Betty White), who happens to be a sister of one of the senior partners, is a nosy bigot. Peter attempts to juggle these issues as well as reconcile with his estranged wife (Jean Smart) and children (Kimberly J. Brown and Angus T. Jones).
Not to be confused with the book of the same name, which was adapted into the movie 21.
This film provides examples of:
- Cain and Abel: Ashley's the Cain to Kate's Abel, with no explanation how Ashley turned out to be such a humongous, racist Gold Digger while Kate... didn't.
- Cathartic Scream: Peter listens to a (presumably long) confession from his teenage daughter about all the things in her life. After hearing this, he very calmly walks upstairs, takes a pillow, holds it to his face, and screams.
- Then proceeds to take a couple pills, then scream into the pillow again.
- Chekhov's Gun: Charlene's tendency to keep things in her bra.
- Double Entendre: The club that Peter, Charlene, and Howie catch Widow and his gang at is called "The Down Low." The term "Down Low" is slang in the African-American community for black men who are closeted homosexuals and have to be discreet in their sexual or romantic pursuits of men.
- Engineered Public Confession: Knowing they would probably check him for a wire, Peter brings a boom box into the back room of the club. When Widow tells him to shut it off, he hits record instead of stop.
- Hate Sink: Ashley, Peter's conniving, manipulative, gold digging, racist, alcoholic, self-absorbed sister-in-law. She brings absolutely nothing to the movie aside from being a gigantic bitch most of the characters can't stand, and to showcase Charlene's toughness when she kicks her ass in the country club bathroom.
- Jerkass: Literally the only person in the movie whom Ashley isn't nasty to is Kate.
- Obfuscating Stupidity:
- Queen Latifah pretending to be the servant. Beyond that, she's demonstrated that she's just as capable at acting "white bread" and "W.A.S.P."-y as Peter and his associates, but that's not who she is.
- Peter putting on his best Pretty Fly for a White Guy act when he sneaks into The Down Low.
- Pocket Protector: Charlene survives a bullet when it hits the cell phone she's been keeping in her bra.
- Pretty Fly for a White Guy: Peter attempts to blend in when he sneaks into The Down Low to meet with Widow. Being a greying old man dressed like a teenaged hoodlum, it works about as well as you'd expect.
- Scary Black Man: Widow (Charlenes ex). He framed her for the robbery that got her put in prison.
- Totally Radical: An attempted aversion, since the writers made up a lot of their own slang rather than risk dating the movie with pre-existing slang.
- Wedgie: At the end of Charlene and Ashley's Cat Fight, Charlene wins after she knocks Ashley out and hangs her on a hook in the bathroom by her bathing suit.
- When You Coming Home, Dad?: Peter starts the film with neglecting his family to keep his career afloat.
- Where da White Women At?: Peter's friend Howie (Eugene Levy) immediately falls for "that cocoa goddess" the second he sees Charlene. Several characters also accuse Peter of having "Jungle Fever" when they see him with her.
- Howie and Charlene do indeed get together at the end. Howie tells Peter to tell Charlene for him that "the cool points are out the window and she's got him all twisted up in his game." Peter gives Charlene the message, and says that's the nicest thing anyone's ever said to her.