Tom gets fired from a record company and tries to start his own music label. He attempts to sign an up-and-coming singer (Teddy Geiger) as his first artist. Meanwhile, Tom's girlfriend pressures him to get married. Gabby: Milena Govich. Phil: Eric Bogosian. Eli: Josh Stamberg.

Tom promises to get a pop princess he once represented to headline a benefit concert his label is sponsoring, but the singer's label won't let her do it even though she is eager to perform. Meanwhile, Mike and Karen interview a young woman to be their child's nanny, but Mike doesn't want to hire her because she's gorgeous and he doesn't trust himself around her. Also, Shooter goes out with a temp from work who is very up front about her feelings.

Tom has a disagreement over the concept of Wayne's music video with the temperamental film director he hires to shoot it. Meanwhile, Jake tries to come up with a catchphrase to use during his sports reports; Bran tries to get her friends to accept her boyfriend Scott; and Mike cares for his neighbors' dog while they are away and worries that he won't be a good father because he can't get the dog to obey him.

Tom reps his former girlfriend's band and is shocked to learn that she may still be in love with him. Adding to Tom's predicament is his promise to get her band booked on "David Letterman," but the show's talent booker won't budge and Paul Shaffer shoots him down. Meanwhile, Jake considers calling his ex-fiancée to tell her that he's gay and that is why he broke up with her, and Mike gets jealous when he learns about a former boyfriend Karen once dated. Aimee Mann appears as herself.

Tom tries to get an influential music critic to listen to a client's CD, but she takes more of an interest in Tom than the band. Meanwhile, Shooter considers buying a bar, but his father is against the idea. Jake fears the public will learn that he is gay and his sports career will be finished if he accepts his boyfriend's offer to move in with him. Bran thinks she may be pregnant and worries how it will affect her relationship with Scott.

Tom discovers the next big thing at a funeral for the owner of his favorite pizzeria. Meanwhile, he's stalked by a street singer who desperately wants that title instead. Dr. John has a cameo as himself.

Tom attempts to get his boyhood music idol, who hasn't recorded in 25 years, in the studio again, but the singer isn't sure he wants to resurrect his career. Also: Tom starts dating an attractive doctor after she rescues him from choking; Shooter considers going into business with a former adult-film star, who now owns her own clothing line; Bran and Jake each hire new interns.