Conner O’Malley on Late Night With Seth Meyers. Photo: NBC

Five years ago, a series of Vines introduced the world outside of the New York and Chicago comedy scenes to Conner O’Malley. These anarchic six-second clips followed a simple formula: O’Malley — playing a deranged car-and-wealth-obsessed man — would pull up to befuddled Manhattan businessmen in sports cars, scream guttural praise for their public display of opulence, and then bike away before they knew what hit them:

The simple comedic pleasures of these Vines got them covered everywhere from BuzzFeed to Autoweek, but they were just the first in a line of characters, videos, and sketches that would showcase O’Malley’s exceptionally specific voice. Starting with this oddly prescient pre-MAGA character, O’Malley has built a cult following with his hyperspecific takes on the unjustifiably paranoid, cyber-vigilant, money-worshipping American male who helped elect a president molded in their own image. Since this batch of Vines, O’Malley has created a vast body of character work on both YouTube and television — where the Annoyance Theatre alumnus got his big break writing for Late Night With Seth Meyers — satirizing Americans bursting with misplaced anger. That, and goofy, sensual dancing to the Charlie Rose show theme song. It’s a lot to take in, so we’ve created this handy guide to one of comedy’s most original voices.

Vine

Watching the first few minutes of “The Transformation,” a fan-made compilation of O’Malley’s best Vines, it’s easy to see why these short clips went viral on BuzzFeed with almost zero context. Only a few years after the worst of the Great Recession, seeing Wall Street execs harassed by a seemingly insane man with a voice like gravel is visceral comic gold. But like much of O’Malley’s work, there’s a cutting darkness underneath it, especially that the reactions from some of the accosted and gaudy one percent, after being told they’re gods, is unabashed pride.

As the Vines advance in chronological order, O’Malley’s character goes from extolling “job-creator pimps” for drinking the blood of the innocent to screaming reverence at a pile of chicken-wing bones in the street. He breaks down at the scene of a car crash, telling the yellow cab and Porsche to stop fighting like a child of soon-to-be-divorced parents. He demonically gurgles at a TV playing an interview between Jay Leno and George W. Bush. And finally, he ends up in what looks to be Joshua Tree desert, wandering alone and sounding like a chain-smoking goblin. It may have started out as a goof, but it’s an achievement that O’Malley was able to form an arc out of yelling at people in Ferraris. It’s also a testament to the torrent of prosaic insanity that New Yorkers experience on a daily basis that O’Malley never got the shit beat out of him. In fact, O’Malley admitted that he and his brother Sean staged the only Vine where he was “attacked.”

In that interview and a rare podcast appearance on Brandon Wardell’s Yeah, But Still, O’Malley described his working-class upbringing on the North Side of Chicago among drunk Wrigleyville bros, Irish and Poles whose hobbies included inter-white racism, and total characters like his father, a mechanic/elevator operator/city inspector who once got fired for drunkenly calling the mayor of Chicago a bitch. It’s these blue-collar midwestern specifics that O’Malley — a former garbage man, as his wife Aidy Bryant revealed — would heighten to extreme levels in his more recent work, most notably TruthHunters.com. Shortly after his Vines gained popularity, it was announced that O’Malley was joining the inaugural writing staff for Late Night With Seth Meyers.

Late Night With Seth Meyers

While Seth Meyers has molded his version of Late Night into a solidly funny, if fairly conventional wrap-up of American politics, O’Malley’s recurring characters veered away from the political and toward the absurd. During his time as a writer from 2014 to 2016, O’Malley’s characters included Gørbøn, a Norwegian black-metal guitarist who telepathically praises Zootopia’s appeal to both kids and parents; Anniversary Guy, who interrupts Meyers to remind him of important anniversaries like the release of Shrek 4Ever After: The Final Chapter in 3D while dressed as a horrifically authentic Shrek; or as himself, doing inspired dances to the theme songs of Fraiser and Charlie Rose. These purely silly characters hearken back to the Late Night of David Letterman or Conan O’Brien, when writer-performers like Chris Elliott and Jon Glaser became household names for comedy nerds who could afford houses. And while O’Malley occasionally did political comedy on Late Night, he saved his darker, more disturbed characters for his own YouTube channel.

YouTube

As the 2016 election heated up, O’Malley started uploading videos on his personal YouTube account featuring a character named Mark Seevers, the founder of an Infowars-type site called TruthHunters. Filmed in Trump-friendly locations like an Orlando campaign rally or the Republican National Convention in Cleveland, the Seevers videos combined man-on-the-street interviews with a narrative about a lonely degenerate who had finally found purpose in his life. In an early video, he finds himself kicked out of an Atlantic City police convention and alone in a parking lot, breaking down over just wanting “a gun, to fucking feel a tit, and to go to sleep and not feel so fucking sad anymore.” But he finds new energy after hitting up the Trump Taj Mahal and the campaign rally, where it stands out how much he doesn’t stand out during Trump’s speech. Nobody bats an eye when he screams “COPS ARE GODS THAT WALK AMONG US!” or tells two nonplussed men about being locked up in a cage by his stepdad.

Besides Seevers, O’Malley’s YouTube channel is a trove of videos starring men who have definitely punched a hole in their wall during the NFL wild card round. Benghazi-obsessed Scott Andrews risks his life to protect his local Wisconsin outlet mall from ISIS supersoldiers (Jo Firestone also stars in the video as his former stepsister and current wife Janet). #MinionSquad features O’Malley walking up and down the Brooklyn-Queens Expressway in an airbrushed Minions T-shirt failing to get people to join a squad that’s never explained (and doesn’t need to be). We even get a reprise of his bicycle Vines when O’Malley runs into Geraldo Rivera and quizzes him on the Fox News personality’s favorite rapper. It’s Eminem, of course.

But the best is Tony Camarabi, NYC’s #1 Masturbator, who ventures to the Exxxotica Expo in New Jersey to discuss his favorite topic, jerking off, with smut peddlers, cam girls, dirty old Jewish men, and way too many people like Tony who are not in character. It’s endlessly rewatchable and the venue is perfect for awkward moments, but it’s when O’Malley gets a physical demonstration of a hands-free masturbation product that shows the clip is more than just jokes about cum and free empanadas. With a glass dildo pressed up against his dick, he and a polite saleswoman bond over their mutual dislike of Obamacare. But when she lets down her guard and vents about barely being able to pay for her family’s health insurance, Camarabi’s mind snaps back to achieving climax. Camarabi would later visit a vape convention and the AVN Awards, the latter as part of a self-produced 22-minute pilot, TruthHunters.com.

TruthHunters.com

The release of TruthHunters.com, a hybrid man-on-the-street and sketch pilot O’Malley made with Joe Pera in 2017, saw O’Malley broaden the scope of his angry, self-loathing failsons by putting them in the same universe. Stylistically, it’s a little like Da Ali G Show, if Sacha Baron Cohen’s creations were men raised on Bang Bros warez and The Matrix Reloaded’s freeway scene. In the opening scene, a user (WhiteMorpheus) clicks open a browser loaded to his favorite sites: TruthHunters.com, AssTube.sex, and Fathers&SonStories.com. We are then reintroduced to Mark Seevers, currently living in his grandma’s centipede-infested basement but no less enthusiastic about then-president-elect Donald Trump. The victory has reinvigorated him with zeal to expose governmental ills, like Diet Coke’s plot to turn white men into trans people, and to defend Daddy Donald Trump at all costs.

In the pilot, we first follow Mark as he travels to Washington, D.C., to provide unwanted freelance security at the president-elect’s inauguration. Interwoven with this plot, in the guise of AssTube.sex and Fathers&SonStories.com tabs, is the return of Tony Camarabi and the introduction of Mr. Conway. Camarabi is in Las Vegas attending the AVN Awards where he faces a tough decision upon learning, while chatting with performers who clearly have deep-seated family trauma, that his 93-year-old grandpa suffered a stroke. On the other side of the country, alcoholic Long Island father Mr. Conway wakes up his young child to teach him a tradition that has been with the Conways for generations: the Charlie Rose theme-song dance.

By the end of the pilot, all three characters have found small wins. Mr. Conway succeeds in passing on his dance moves and enjoys a midnight cigarette with his 10-year-old son. Tony learns his grandpa is okay and gives a speech at the AVN Awards, entreating the audience to respect their bodies because some people are too sick to jack off. And Mark, after struggling to provide security and being rebuffed by Alex Jones himself, returns to Rosemont, Illinois, with a fantasy of finally owning a Porsche 911. Sound familiar? From his Vines to TruthHunters.com, O’Malley’s sad, entitled men rage against the traitors, women, and weak-willed cucks who held them back from reaching their true potential. In a comedy landscape inundated with Jon Stewart copycats, it’s a shame that no network took a chance on this abrasively subversive look at the Americans who decided that November 8, 2016, was the first time that they would make their voices heard.

2Nite Show Starring Johnny Carson

A one-off special filmed in 2016 and released on JASH’s YouTube channel the following year, 2Nite Show Starring Johnny Carson posits a nightmarish version of the classic talk show. Written by and starring O’Malley as the late-night host, it doesn’t subvert The Tonight Show in the ways you’d expect. Sure, O’Malley and his guests, including Anna Nicole Smith and vampire hunter Blade, are caked in garishly hideous makeup, and he tells more monologue jokes about clits than the real Johnny Carson. But it’s the old commercials and clips from the early ’90s that do the heavy lifting.

Found by editor Andrew Peyton, these VHS-quality gems were intended, as O’Malley explained in an earlier Splitsider interview, to replicate the feeling of watching an older brother channel-flip. And while there’s amazing Midwest-specific footage of old Jewel-Osco ads and the Paragon Cable channel guide, it’s the rapid-fire cut of brutally homophobic jokes from In Living Color, Andrew Dice Clay, and Eddie Murphy that reminds viewers how casual bigotry flourished in both genial late-night TV and mainstream stand-up comedy. After Carson follows these clips with fan-favorite character (in this universe) Gay Voice, he interviews NBA announcer Marv Albert and nonchalantly asks him to describe his infamous sexual assault in the same way, say, Jimmy Fallon would ask the Rock to describe a prank he pulled on the set of San Andreas. With basketball-arena music blaring in the background, the audience cheers on Albert as he casually describes beating his lover for refusing to have sex with him. In real life, Albert’s only punishment was a quickly reversed firing and a deluge of late-night jokes about his penchant for cross-dressing and biting that were revealed during the trial. Visually, 2Nite Show might seem like it’s stretching to portray its macabre satire, but it more or less realistically depicts how the media covered sexual assaults until about eight months ago.

Frequent Collaborators

Joe Pera: O’Malley and soft-spoken comedian Joe Pera are partners in a production company, Chestnut Walnut Unlimited, that recently produced Pera’s Adult Swim series Joe Pera Talks With You. Unusual for both Adult Swim and O’Malley, JPTWY is quiet and tender but no less uproariously funny as they, along with director-editor Marty Schousboe, distilled Pera’s grandfatherly persona into a comedy unlike anything you’ve seen before. Besides writing and producing it, O’Malley plays Pera’s neighbor on the show, a beaten-down family man whose only goal in life is to eat the perfect bite at breakfast. Other than appearing in small roles in TruthHunters.com and directing many of O’Malley’s YouTube videos, Pera also co-starred in the web series How to Make It in USA as the struggling actor foil to O’Malley’s revolting talent agent.

Carmen Christopher: Another Chicago native, NYC-based comedian and Chris Gethard Show writer Carmen Christopher’s collaborations with O’Malley have yielded two of their funniest works: Wrigleyville Cubs Playboys and Guys Day. In the first, the duo star as Mark and Matt, two Cubs fan bros living what they think is the Entourage lifestyle in their cramped Addison Street apartment. In this video (and its post–World Series victory follow-up), the boys explain their deeply held beliefs in rapid takes: loaded nachos are amazeballs, affirmative action is messed up for white people, and it’s badass to put on a suit and make your girlfriend cook you a steak. Intercut with actual footage of Wrigleyville bros drunkenly fighting each other, it’s not too far off from the post-gentrification North Side inhabitants they’re lampooning.

A slightly different version of these characters makes a return in Guys Day, a beautifully shot short film that takes place in a rainy, nearly desolate Atlantic City. Their lives are unfair — from girlfriends who catch them cheating to mean co-workers at Enterprise Rent-A-Car — but this day is for the boys, and nobody is going to stop them from getting screwed up on Absolut and Sprite underneath the pier. O’Malley also co-stars in Christopher’s Little Banks on Wall Street, a web series that follows a pathetic telemarketer who decides to change his life after reading The Wolf of Wall Street.

TV Appearances

When not starring in his own work, O’Malley has shown up in several comedies shot in New York, often as the love interest of his wife Aidy Bryant, whom he first met at Chicago’s Annoyance Theatre. On Broad City’s season-two finale, the pair played an annoying comedy couple who won’t let Abbi and Ilana have a moment of peace in a Chinese restaurant. On Horace and Pete, where Bryant starred as Louis C.K.’s estranged daughter, O’Malley made an appearance as her boyfriend. And on truTV’s At Home With Amy Sedaris, O’Malley played a nearly mute alien named Guanog whose flirtations with Sedaris cause her and Bryant, playing an alien queen, to battle for his love.

O’Malley also made frequent appearances on two of NYC’s most beloved public-access TV shows, The Chris Gethard Show and its replacement, The Special Without Brett Davis. On the former, O’Malley recurred as Beast Masturbator, who saves NYC from rapist ghouls and goblins by jerking them off, while on the latter he played a former cult follower who now devotes his life to Chicago horror-movie host Svengoolie.

And in his most unlikely role, O’Malley guest-starred as a young version of Louis C.K.’s alter ego in Louie’s season-four episode “The Elevator: Part Four.” In an extended flashback where Louie impregnates his wife on what was to be their last night together, O’Malley nails the pitiful mannerisms of the now-disgraced comedian we once loved. But he doesn’t simply do a caricature; he carries ten minutes of prestige television in a subdued, dramatic role. The emotional root of his performance isn’t too far from his own characters, the main difference being that Mark Seevers & Co. deal with their sadness by lashing out at the world instead of being resigned to their depression. It’s an unexpected turn that displays latent talents that he’ll hopefully show in the long career ahead of him.

In a relatively short span, O’Malley has demonstrated a very specific talent for finding the funny in rage. Plenty of comedians play pissed off, but by latching onto the id of the Great North American MAGA Male, he’s found a way to satirize the driving force of evil in politics and culture by cloaking it in a veil of absurdist stupidity. And with the state of the world being what it is, he won’t be running out of influences anytime soon for his enraged dolts angry at the wrong things for the wrong reasons.