Robert’s foray into acting started when he was 6, after being discovered by his manager Jeff Mitchell of J. Mitchell Management. He was walking down the street in Manhattan with his dad. Immediately, he was hired to appear in a Pizza Hut commercial. However, he opted to be just a “regular kid” and chose not to appear in the commercial. He “retired” from show business and decided to concentrate on school, sports, and his friends.
When Iler turned 10, he decided to give show business another try, as he appeared in several commercials and a feature film called The Tic Code. He then bagged the biggest role of his career after he was cast as Anthony Jr, the son of the big boss Tony Soprano on the HBO series The Sopranos. With the role, he received a Screen Actors Guild for best ensemble cast for his role on the mafia-themed series. He also bagged the Hollywood Reporter’s Young Star Award for best young actor in a drama TV series for two years in a row in 1999 and 2000 on The Sopranos. His other credits include the 1999 film Tadpole, alongside Sigourney Weaver and John Ritter, and Daredevil, with Ben Affleck.