Celebs Who Have Done A Lot Of Jail Time

If actor Lillo Brancato Jr.'s face looks familiar, you may recognize him from his roles in The Sopranos (1999-2007) and A Bronx Tale (1993), or you may recall that in 2005, he was involved in a robbery-gone-wrong in the Bronx that resulted in his associate killing an off-duty police officer. Yeah, that.

According to ABC News, Brancato Jr. was deep in the throes of heroin and crack-cocaine addiction. Craving a fix, the actor and a friend, Steven Armento, attempted to break into the home of another friend, who happened to live next door to NYPD Officer Daniel Enchautegui. When Enchautegui confronted the would-be thieves, Armento shot, fatally wounding him, but not before Enchautegui returned fire, hitting both Brancato and Armento.

Armento got a life sentence. Brancato was sentenced to ten years in jail for attempted burglary in 2008. He was released in 2013 and has returned to acting. "There isn't a day that goes by that I don't think about that night and wish that I could change the outcome," he told the Daily News in 2014, adding, "Unfortunately, we can't do that in life." Incredibly, Brancato was later photographed mingling with NYPD officers in 2016.

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