" Dolls and Dolls " Will & Grace episode "Dolls and Dolls" is the twenty-first episode of the fifth season of the American television series Will & Grace . It was written by Kari Lizer and directed by series producer James Burrows . The episode originally aired on the National Broadcasting Company (NBC) in the United States on April 24, 2003. Singer-songwriter Madonna guest starred in "Dolls and Dolls". In the episode, Karen ( Megan Mullally ) is prompted to meet "real people", and finds a peculiar office worker named Liz (Madonna), and becomes her roommate. Meanwhile, when Will ( Eric McCormack ) sprains his ankle, he develops a habit of taking too many painkillers , and his drastic personality change prompts a concerned Grace ( Debra Messing ) and Jack ( Sean Hayes ) to intervene and interfere. "Dolls and Dolls" received mixed reviews from television critics. According to the Nielsen ratings system, t