16. “After fucking your wife, I’ll take two.”

Courtesy of: Joe Hallenbeck (Bruce Willis) in The Last Boy Scout (1991)

Very few Hollywood actors can nail an insulting one-liner quite like Bruce Willis, who filmography is worth of its own similarly themed list. In The Last Boy Scout, his buddy action comedy co-starring Damon Wayans, Willis injects a healthy dose of emasculation into his best quote, which is only served justice when presented in its full glory:

Random Thug: Wrong place, wrong time. Nothing personal.
Joe Hallenbeck (Willis): That’s what you think. Last night, I fucked your wife.
Thug: Oh, you did, huh? How’d you know it was my wife?
Hallenbeck: She said her husband was a big pimp-lookin’ motherfucker with a hat.
Thug: Oh, you’re real cool for somebody who’s about to take a bullet.
Hallenbeck: After fucking your wife, I’ll take two.

Not even Damon “Homey the Clown” Wayans could out-funny Willis in The Last Boy Scout.