A true “if you know, you know” comic genius, we were thrilled to see Conner O’Malley’s feature debut Rap World have a rare cinema screening in Auckland last month. If you’re asking “Conner who?”, Tom Augustine is here to explain what the deal is – with plenty of O’Malley’s finest moments – and his new film Rap World here to watch in all its glory.
Is Conner O’Malley a madman or a visionary? Judging by the extensive and eclectic output from the American comedian over the last few years, probably a bit of both. From standup to writing on the best alternative comedy shows of the modern era, to iconic guest appearances on shows like I Think You Should Leave, Detroiters and Joe Pera Talks With You, to his bizarre YouTube videos, O’Malley is fast becoming the comedy savant’s favourite around the world.
In September, the Capitol Cinema Film Club (join the Facebook page for future announcements!)—which aims to screen rare and underseen gems from cinema history at a low price month to month—exclusively screened O’Malley’s debut feature Rap World, a raucous found-footage mockumentary about a group of schlubby Midwestern burnouts who try to record a rap album over the course of an evening. It does not go well.
Those who know O’Malley’s work will recognise familiar themes—most importantly, a depiction of modern-day white male fragility that manifests in extreme ways when it comes into contact with the digital age. For those who haven’t encountered O’Malley’s work before, here’s where to start:
The I Think You Should Leave skits
Conner is probably most broadly recognised from his uniquely unhinged work on Tim Robinson’s I Think You Should Leave, headlining some of the most iconic scenes from Robinson’s ingenious comedy series. There’s ‘Honk If You’re Horny’, in which Conner plays a man who is triggered by a bumper sticker bearing the slogan; or ‘Laser Spine Specialists’, in which Conner is a shady record executive who lures sad middle aged men into recording albums at cost (‘this is right in your Q zone!’).
More recently, there’s the ‘Frankenstein’s Chick’ scene, in which O’Malley hounds a co-worker to watch his internet videos, which escalate into more and more bizarre scenarios. It’s a great primer for O’Malley’s style—brash, loud, tense and antagonistic.
Detroiters and Joe Pera Talks With You
Two of the best alternative comedy shows of the last ten years featured O’Malley in key supporting roles. On soft-spoken comedian Joe Pera’s Joe Pera Talks With You, O’Malley is more subdued but still hilarious as the forlorn husband of Pera’s sister, obsessed with achieving the ‘perfect egg bite’.
On the enormously underrated Detroiters, O’Malley again plays against Tim Robinson as Robinson’s burnout younger brother who may just be more talented at advertising than Tim (who has started an ad business in Detroit). It culminates in this glorious scene, which is all the funnier for Robinson being so close to breaking throughout— ‘you don’t need your Slipknot mask!!’.
Late River with the River Guy – The Only Talk Show in a River
It’s fair to say the legend of Conner O’Malley started to hit the alt-comedy mainstream with these uniquely unhinged videos, which feature a besuited O’Malley hosting a ‘talk show’ in the middle of a river, to understandably bizarre ends.
Stand-Up Solutions
It’s been a killer year for Conner—not only is he releasing Rap World and the short film Coreys (which will play before the feature this Friday), Conner also released The Mask (see below) and this hour-long stand-up special that demonstrates the comedian’s incredible range.
Sharing DNA with Tim Heidecker’s An Evening With Tim Heidecker, Conner creates a persona—a miserable suburban dad who upends his life by investing in an AI model that aims to revolutionise stand-up comedy. It’s high-concept done right—and arguably the best stand up special of the year.
The Mask and 103 Fever
Two of O’Malley’s most impressive recent digital shorts are these ones, which demonstrate O’Malley’s growing production value and ambition. The first is a tragedy in miniature about an idealistic suburban teen who loses his soul as he tries to become a great comedian.
The second is a batshit internet nightmare about a man who has a fever that hasn’t broken for six months.
The Howard Schultz Saga
O’Malley at his most aggressively frightening, which is saying something, this is a masterpiece of abject modern dread (which is also still very funny). It is also the only O’Malley video to my knowledge with a graphic content warning on YouTube.
Ostensibly about Starbucks CEO Howard Schultz’s biggest fan—who goes absolutely nuts about the potential for Schultz’s ill-fated independent 2020 Presidential run—it has the feeling of a disturbing Reddit video you might find on a thread about a serial killer.
Vine
One of the first places O’Malley started popping off was on the now-dead video sharing app (RIP), where users got short, sharp exposure to the ‘crazy man babbling on the sidewalk’ style of comedy he’d later perfect.
The most famous is perhaps the ‘I Have the Power of God’ vine, which is an early example of a common element of O’Malley’s work—wondering how the hell he pulled it off.
Truthhunters and other Political Videos
Naturally, O’Malley’s inclination toward characters who are conspiracy wackos and seedy reflections of the American underbelly finds purchase with the supporters of one Donald J Trump.
In 2016 and beyond, O’Malley regularly produced on-the-scene reports at Trump rallies and the like, including getting up close and personal with Alex Jones. It demonstrates that O’Malley’s comedy isn’t just firing randomly, but has laser-focused precision when tackling the esoteric and disturbing oddities of modern culture.
Rap World
Uniting with fellow alternative comedians Eric Rahill and Jack Bensinger and directed by O’Malley himself alongside editor Danny Scharar, Rap World represents O’Malley’s stab at a traditional narrative—which is to say it isn’t especially traditional at all. Instead, this 56-minute found footage mock-doc is a cutting portrayal of white suburban malaise packaged within an incredibly funny ‘night-gone-wrong’ saga.
It features one of the funniest and most devastating cuts/sight gags in history toward the end. It might just be the funniest movie of the year.
Updated from a piece originally published on Flicks on Sept 24, 2024.
