A lot of terrifying violence is made cinematically digestible through humor. That certainly extends to all of the villains below. This list spotlights a murderers' row of violent villains who are nevertheless frequently funny, even through their dastardly dealings.
These movie (and TV) maniacs' predilection for bloodshed as a less-than-constructive means of problem-solving is often weirdly, hypnotically chuckle-inducing, thanks to their gallows humor. For further reading along these lines, check out our lists of funny villains in serious movies and the funniest movie villain kills.
- Photo: HBO
The Sopranos hitman Paulie "Walnuts" Gualtieri (Tony Sirico) is as quick with a quip as he is with a pistol. Indeed, that's part of the fun. He kills many, many people as a trusted lieutenant for crew leader Tony Soprano (James Gandolfini) throughout the show's six seasons. But the levity of the character makes him weirdly endearing to his audience.
A good example of the duality of Paulie occurs in "I Dream of Jeannie Cusamano," the 13th and final episode of the show's first season. Paulie and Christopher (Michael Imperioli) are pursuing Mikey Palmice (Al Sapienza) through a leafy suburban forest, determined to kill him after Tony discovers that he and his boss Uncle Junior Soprano (Dominic Chianese) - as well as Tony's mother Livia (Nancy Marchand) - were behind a recent attempt on Tony's life. Paulie runs through some poison ivy and can't help but kvetch and pick at the subsequent rash, even as he and Christopher gain the high ground against Mikey and brutally murder him. Like a lot of characters on the show, Paulie is an amoral psychopath, but a pretty funny one.
- 2116 VOTESPhoto: Warner Bros.
The most memorable gangster movies (and certain gangster television shows) often benefit from breaking up some of their understandably bleak murder montages with tactical pepperings of character-based comedy.
Along these lines, one of the greatest comic performances ever arrives in the form of Joe Pesci's Oscar-winning turn as Tommy DeVito in Goodfellas (1990). Short in stature but big in confidence, Tommy is a web of contradictions. A crack-up at dinners with an itchy trigger finger, Tommy can go from mother-appreciating jokester to friend-murdering maniac within seconds. "You're a funny guy," his comrade Henry Hill (Ray Liotta) tells him in perhaps Tommy's most memorable moment. Henry and Tommy are enjoying some adult beverages in smart suits with their mob cohorts in a preferred haunt, the Bamboo Lounge, and had been chuckling about one of Tommy's many entertaining anecdotes. Tommy suddenly flips to deadly serious mode. "Funny how? I mean, what's funny about it?"
Suddenly, the laughter percolating around Tommy's story disappears completely. The mood has shifted. Everyone knows what this line of inquiry could lead to. "I mean, I'm funny how? I'm funny like a clown? Like I'm here to amuse you?" Tommy continues to berate Henry, who tries to defend his compliment, explaining that he enjoys the way Tommy tells his tales. Things get tense.
There is a pregnant pause.
Henry calls his friend's bluff, and the mood lifts. Tommy was trying to freak Henry out. But we certainly know that Tommy, a fount of barely contained rage in his better moments, is capable of doing anything to almost anyone, friend or not. We later witness similar instances of Tommy's wrath against supposed allies (and a few foes he perhaps shouldn't cross) in several memorable subsequent scenes.
- 394 VOTESPhoto: Lions Gate Films
Corporate raider/deranged cannibal/obsessive Phil Collins fan Patrick Bateman (Christian Bale), as realized in Mary Harron’s brilliant American Psycho (2000), represents an achingly on-point parody of a certain kind of amoral yuppie who continues to more or less run rampant - even today. Bateman, of course, takes things to an obscene extreme, exploiting the evils of enterprise while simultaneously crying for help via a killing spree.
Bateman is prone to rambling Rolling Stone magazine-channeling reviews of the disposable pop records of his day, frequently delivered to his victims during their last moments of life. He’s also a big fan of a well-made business card.
- 470 VOTESPhoto: Warner Bros. Pictures
By 2006, Jack Nicholson the actor had been more or less subsumed by Jack Nicholson the movie star in the popular consciousness. So it only made sense that his last great performance to date was in Martin Scorsese's Oscar-winning crime masterpiece The Departed (2006) as Frank Costello, a fairly accurate fictionalization of real-life Irish Boston crime boss Whitey Bulger, still a fugitive at large at the time of the movie's release. Scorsese, like Nicholson, has always been a master when it comes to balancing comedy and violence.
We witness the unraveling of Frank Costello and his empire throughout the movie. After he recruits Colin Sullivan (Matt Damon) to infiltrate the Massachusetts State Police as a star cadet, Frank soon realizes that Boston's finest may have one of their own infiltrating his operation, too. Indeed they do, and it's Billy Costigan (Leonardo DiCaprio), one of Frank's trusted young lieutenants. Soon, everyone's paranoia is (justifiably) on the rise. Frank, always one to dish out comic gestures at deeply inappropriate times, takes to wearing luxurious bathrobes, leaning into weird prop comedy, consuming exorbitant amounts of cocaine, and impersonating rats. Nicholson takes the Jack Torrance/Jack Napier approach here, effectively Nicholsoning it up just as much as we would hope in a performance that is at once bitingly funny and deeply disturbing. Never for one minute do we forget just how lethal this guy is, even in the midst of the yuks.