Iler appeared in the video for Marilyn Manson's single "Dope Hat" (1995).
By mid-1997, he was appearing in commercials for Pizza Hut, and attending three or four auditions a week. He had also appeared on Saturday Night Live and in some film parts, but nothing that brought him great recognition. It was then that he won the role of A.J. Soprano, the son of series lead Tony Soprano, on the HBO drama The Sopranos, which aired from 1999-2007. By May 2001, he had begun home schooling for his education.
Iler was present on October 23, 2005 when the underground poker club Ace Point was raided by the police.
