By them time she was hired to play Stacey Paterno, the mayor's feisty right hand, Esposito was filming a recurring role as a gangster's daughter on Fox's "New York Undercover.” The actress had decidedly pointed opinions about her sitcom character should dress and behave and gradually the writers and producers allowed her to make some modifications in her character. Still, Esposito felt unchallenged and after little more than a season and a half, opted to quit the show in favor of concentrating on a big screen career. By that time, she had played a bartender in the summer sequel "I Still Know What You Did Last Summer" (1998) and had twice worked with Spike Lee, most notably in her breakthrough role as Ruby, an aspiring punk singer whose boyfriend (Adrien Brody) is suspected of being the notorious Son of Sam killer in "Summer of Sam" (1999). Additionally, she had a prominent part in "Side Streets" and made a cameo appearance in the Chris O'Donnell vehicle "The Bachelor" (both 1999).

After playing several small dramatic roles in major pictures and starring in the low-budget independent thriller "The Proposal," Esposito landed a starring comedic role opposite Dana Carvey in "Master of Disguise" and played alongside William H. Macy, Sam Rockwell and George Clooney in the Russo Brothers' caper comedy "Welcome to Collinwood," both released in 2002. In late 2004 Espoito returned to series television with a recurring role on the CBS courtroom drama "Judging Amy" playing Crystal Turner, a social worker who runs an outreach program for homeless children. She followed up on the big screen as a member of the top-flight acting ensemble assembled for the racially charged, multi-plot drama "Crash" (2005), playing the partner and lover of a police detective (Don Cheadle) embroiled in a racially sensitive homicide case. Esposito then returned to series television in the one-hour drama, “Related” (WB, 2005- ), about four New York sisters trying to keep their heads above water while dealing with the demands of work and family.