Before turning to acting, he was convicted of several crimes and had been arrested 28 times. In 1967, he was sent to prison for robbing a Brooklyn after-hours club, but was released after serving 13 months. In 1971, he pleaded guilty to felony weapons possession and was sentenced to an "indeterminate" prison term of up to four years, of which he ended up serving 20 months. It is alleged that he was an associate of Colombo crime family captain Jimmy "Green Eyes" Clemenza during the late 1960s to mid 1970s. In a 1989 interview, Sirico has admitted that he has spent prison time within several penitentiaries including Woodbourne, Sing Sing and Wallkill. In 1999, he and Sopranos co-star Vincent Pastore were seen meeting Clemenza and his brother, a Colombo soldier, at a Christmas party in Little Italy; Clemenza was under FBI surveillance at the time. He has said that during his imprisonment, he was visited by an acting troupe composed of ex-convicts, which inspired him to give acting a try. According to a court transcript, at the time of his sentencing, he also had pending charges for drug possession. He appeared in a 1989 documentary about life, The Big Bang, by James Toback, in which he discussed his earlier life.