In 1995, Rispoli gave a brilliant breakthrough comedic performance in the successful romantic comedy "While You Were Sleeping," playing Sandra Bullock's tenacious lovestruck neighbor Joe Jr, a man with an eye for Bullock's Lucy, and another hidden passion. As the obnoxious and overbearing Joe Jr, Rispoli stole every scene he was featured in, and managed to make the otherwise creepy character especially endearing. Also that year he was featured in a lower profile role in Gus Van Sant's black comedy "To Die For." The following year saw him turn in solid performances with supporting roles in "The Juror" and "Homeward Bound II: Lost In San Francisco." In 1997 the actor starred in the Canadian independent film "His and Hers," a zany comedy starring Liev Schreiber and directed by Hal Salwen. That same year he was featured in the disaster film "Volcano." 1998 was a busy year for the actor, who turned in higher profile supporting roles in "Snake Eyes" and "Rounders," marking his most high-profile work in mainstream film since "While You Were Sleeping." He also has a smaller role as a detective who clashes with Stephen Baldwin's unorthodox Bo Dietl "One Tough Cop." Rispoli would next tackle a featured role in Spike Lee's "Summer of Sam" (1999), with a frighteningly dead-on portrayal of a neighborhood tough looking to take down the serial killer terrorizing New York City in this Bronx 1977-set drama. This role would garner the often overlooked actor much-deserved acclaim and notice, identifying him as one to watch. He replaced actor Daniel Baldwin in the cast of the romantic comedy "It Had to Be You" (lensed 1998) and starred as a factory worker in the 1956-set independent drama "Two Family House" (2000). In addition to his film work, Rispoli spent many years on stage, performing with the Steppenwolf Theater and co-founding the Willow Cabin Theater Company. WCTC staged a production of "Wilder, Wilder, Wilder--3 by Thornton" that moved to off-Broadway and later to Broadway, earning a Tony nomination. Rispoli has appeared in New York and regional theater, acting in productions of "Macbeth," "Tartuffe" and "A Midsummer Night's Dream" as well as working as an understudy in the revival "Balm in Giliad." Rispoli also appeared extensively on television, working early in his career on the daytime dramas "One Life to Live" (ABC) and "Another World" (NBC). In 1995 he starred in the short-lived Fox series "The Great Defender," playing the street-smart Lou Frischetti, a nonconformist but highly effective attorney. The following year saw him on CBS with the even shorter lived "My Guys," a New York City-set sitcom starring Rispoli as a widowed father of two. An overly formulaic and crude sitcom, its cancellation would prove a boon to the miscast actor. In 1998, he guest starred in the popular NBC dramas "Law & Order" and "ER." "Scarred City," a police thriller feature starring Rispoli screened at Cannes and premiered on HBO later that year in lieu of theatrical release. In 1999 the versatile actor guest starred on HBO's acclaimed original series "The Sopranos" and also was featured in an episode of "Touched By an Angel" (CBS). In 1999. Rispoli landed the role of a veteran cop partnered with a rookie in the short-lived Fox police drama "Ryan Caulfield: Year One." In 2002, he co-starred in the television series "Bram and Alice."