Dying’s easy, comedy’s hard. But killing off heroes is delightful. It’s always admirable to see comedians taking dramatic roles, if they do it well. It feels good to make ‘em laugh, but it feels even better to kick ass. Any idiot can be a hero, but it takes true talent to sink your teeth into a proper villain. And not just someone who spouts horrible lines while shooting hostages. I mean, someone psychologically damaging, someone you long to see suffer a horrible, painful, prolonged demise. Someone you physically loathe, you scowl at. And since most comedians bank on a loveable and jovial persona, it’s always wonderful to see them take that dark turn, to portray someone who’s represents the other dramatic mask.
This was a delightful albeit difficult list to compile. I wanted to display actors who are known more for comedic or lighthearted fare, who took on the mantle of a truly evil and reprehensible villain. I didn’t want to include Sho Nuff or Ernie McCracken, brilliant but hilarious baddies in their own right. And although you would be hard pressed to find better villains than Darth Vader or Hans Gruber, I didn’t feel like James Earl Jones and Alan Rickman were really what you’d call lighthearted — though both actors have played to great accolades in comedies. That the same reason I hemmed and hawed before discounting Alexander Godunov, the second in command from Die Hard as well as many other wicked characters who put forward a genius comedic turn as Shelley Long’s Maestro in The Money Pit. I also decided against including perhaps the most famous of the good guys gone bad — Henry Fonda’s child-wasting black hat in Once Upon A Time In The West and Fred Macmurray in Double Indemnity. I left off Christopher Walken and Dennis Hopper, mostly because they defy any sort of cubbyhole, other than one reserved for awesomeness. And while they were great, I had to leave off Gene Wilder, Steve Martin, Martin Short, Jim Carrey, and Joan Cusack for the ten I finally decided on.
Below, you will find a compilation of some of the most heinous folks ever to grace the silver screen. They cast aside their clownish and glee to chill us to the bone. Comedy often comes from dark places, and these comedians went dark.
Denis Leary — Fallon, Judgment Night
Four morons peeled straight from a lazy CBS sitcom find themselves stranded in an RV in the bad part of town. What might seem like the opening to a really bad buddy comedy takes a turn for the brutal thanks to Denis Leary’s stone cold Fallon. Part drug dealer, part crimelord, Leary hunts the suburban quarry through the roughest parts of Chicago. Begging for their lives won’t help, money won’t help, nothing will satisfy Fallon except for their deaths.
Robin Williams — Seymour Parrish, One Hour Photo
There was a time when Robin Williams really wanted to be a bad, bad man. In the span of just one year, he portrayed the insanely zany Rainbow Randolph in Death to Smoochy, and the shy Alaskan menace against Scarface and Horseface in Insomnia. But it was his turn as the disturbing photo developer Seymour Parrish in One Hour Photo that was truly chilling. Seymour wasn’t overtly violent or threatening, he just exuded that get-under-your-skin creepiness that was so unnerving. Even as a serial killer, he wasn’t nearly as ghastly as the quiet anger beneath that bizarre blonde head of hair.
Jon Lovitz, Cheri Oteri, and Nora Dunn — Bart Bookman, Zora Charmichaels, Cyndi Pinziki, Southland Tales
I rag on Southland Tales, because it was like trying to eat a buffet from a single bowl. There was so much going on it was confusing and chaotic, and just a massive mess. But within the insanity, there was a trio of “Saturday Night Live” also-rans who Richard Kelly chose to play some truly wicked folks. Nora Dunn always plays a convincing meanie, always verging on the somewhat comedic. Cheri Oteri actually looked like she was going to kill someone, and watching her beat the hell out of people was probably one of the few joys in my life. But it was Jon Lovitz who truly kicked my ass as the racist vicious cop. Todd Solondz showed us that Lovitz can be unbelievably creepy, but Richard Kelly showed us that Lovitz can actually be a badass. And again, with the fucking blonde hair.
John Lithgow — Blake, Ricochet; Qualen, Cliffhanger
I don’t know if it’s entirely fair to consider Lithgow a comedian necessarily, though I think he’s earned more fame for his comedic turns like The World According to Garp and Harry and the Hendersons. But there’s something of the truly Shakespearean evil when Lithgow puts on the black hat. He’s got a number of outstandingly over the top villains in his repertoire, including the understated Reverend Shaw Moore in Footloose. When Lithgow’s evil, he doesn’t play it subtly, but rather with a scenery chomping, mouth-foaming glee. In Ricochet, Denzel puts him prison, where he spends his time fighting Nazis with samurai swords and phone book armor and plotting a diabolic revenge. I actually preferred him as Qualen in Cliffhanger, lurching around in the snow killing people with cold-hearted abandon and doing battle with The Stallone.
Bette Midler — Mona Dearly, Drowning Mona
There weren’t many ladies on my list of comedic baddies, because if there’s one thing harder for an actress than convincing people she’s funny, it’s convincing them that she’s also evil. The Divine Miss M spent most of the late ’80s playing many wicked witches named Barbara in such darkly comic pics as Ruthless People and Down and Out in Beverly Hills. For a darling diva, she could be an evil, evil bitch. And it was as the titular Mona Dearly in Drowning Mona that Bette hit her epically mean ass stride. In the strange comedy, Bette Midler was so horrific that everyone in the little town wanted her dead. Though told in flashback, it was incredible watching Midler tear her claws into everyone.
Tim Curry — Pennywise, IT
Alright. It’s probably a stretch to put Tim Curry on my list. He probably belongs in the same category as Hopper and Walken, in that he kind of defies categorization. He’s run the gamut of villains from fantastical to absurd to mustache-twisting baddie. And yet, as the nightmarish clown that floats down in the sewers of Stephen King’s IT, he’s the only portrayal of a novel villain that actually made me unable to read a book until years later. And still that massive grin, that thick otherworldly cackle, still haunts me to this day. Clowns freak people out, but Tim Curry pretty much put the last stake in the big tent.
Dan Akyroyd — Grocer, Grosse Pointe Blank
Though really a comedy, Grosse Pointe Blank was actually a pretty goddamn good hitman flick. And while it was hard to truly fear him, Akyroyd put forward a spectacular performance as the foil to Cusack’s Martin Blank. I never would have thought the pear-shaped comedian could pull off violence so well, he proved me wrong. Akyroyd played Grocer with a giddy maniacal abandon, a happy hitman taking out the competition. I’d actually like to see Akyroyd take the dark route like some of his other cohorts on this list. I think if you put him in something as dark as the stuff that Robin Williams has done, he would really shine.
Billy Connolly — Il Duce, The Boondock Saints
The grinning comedian with the wolfman beard took over for Howard Hessman on “Head of the Class,” and is know more for his almost John Cleese-like banter and wit. So when he faced down the two avenging angels in The Boondock Saints with his six-gun vest and Lennon sunglasses, it was like watching Sean Connery in his old-age prime. Il Duce was a bad ass of epic proportions, caged up like Hannibal Lecter, unleashed on the two prayer-filled vigilantes as the only thing that could possibly stop them. It is Billy Connolly who elevates the cult film to epic status.
Rodney Dangerfield — Ed Wilson, Natural Born Killers
When Oliver Stone meets the stormfront of Quentin Tarantino, it’s hard to really delineate between good guys and bad guys. Everyone seems like they’ve got issues. But Rodney Dangerfield is incredibly hideous as the molesting menace that sets off Mallory in this Bonnie and Clyde redo. A fat wretched letch, his scenes actually have a greasy pork smear of disgust to them. You actually feel worse for having seen them, like they are staining your soul.
Mo’Nique — Mary, Precious
I waited to write this list solely based on the legend of Mo’Nique’s portrayal of the evil mother in Precious, and she didn’t disappoint. What makes Mary so scary is that she’s like the crocodile that haunts Captain Hook. She lounges around, grinding to dance videos, smoking cigarettes out of the side of her mouth, before lashing out with incredible violence. She carries an aura of hatred and meanness, thunderclouds on the horizon that’ll destroy your entire home. She’s relentless, calculating, and cruel, and one of the scariest things I’ve seen on screen in a long time.