In the porno theater scene of “The Departed,” Nicholson disguises himself as a fellow moviegoer. He approaches Damon and appears to reach for a gun but instead whips out a dildo. “Jack’s idea was ‘So here’s the deal — I’m going to come in and I’m going to sit there in the overcoat and I’m gonna turn around and pull out the big dildo and we’re gonna laugh,'” Damon recalled the Hollywood legend telling him.
The young actor was inspired by what Nicholson was doing. “Jack really brought this incredible new element to that character,” Damon insisted. “He made him more obscene in a way that felt authentic, because these guys sublimate sex into violence and violence into sex and it really is how a lot of those things did occur.”
By introducing this vulgarity to his character, Nicholson allowed Damon to expand upon his own character as well. “If Jack was introducing this sexual element, then I thought it was fair game in the script, and that we had to reference this from my character Colin’s standpoint,” he explained. This inspired him to introduce a new side to Colin. “We’re in this macho world where everyone’s beating each other up… and Jack’s a sexual dynamo – so here’s what I want to do: I want to lose every fight I’m in and I don’t want my d*** to work,” Damon told the director.
The work of these two actors added a new thematic layer to the film that strengthened it on the whole. Nicholson may have shocked Damon when he pulled out a dildo on set, but he scared him into an ingenious idea.