Born in New York City, he appeared as a child actor alongside his father in such films as Charley Varrick (1973), The Bad News Bears (1976) and House Calls (1978). Among his directorial projects have been The Grass Harp, from a novella by Truman Capote, and the made-for-TV movie The Marriage Fool, both of which starred his father. He also directed Doin' Time on Planet Earth (1988), Her Minor Thing (2005), Baby-O (2009) and Freaky Deaky (2012), which premiered at the Tribeca Film Festival.

He was named for his godfather, actor Charlie Chaplin. He attended the University of Southern California, where he met his first wife, Michele Bauer, BA, Masters, Law. He and his current wife, Ashley, were seen on an episode of HGTV's Selling New York in June 2013. Ashley is a Dancer and working on her own teahouse.