O'Malley began his comedy career at the Annoyance Theatre, where he met his future wife, Aidy Bryant.[7] When Aidy was cast on SNL, the couple moved to New York, and O'Malley began uploading short comedy videos to the social media platform Vine, while working a day job as a dog walker.[8] O'Malley's videos quickly began to gain attention and acclaim, and in 2014, he was hired as a writer for Late Night with Seth Meyers.[9][10] While writing for Late Night, O'Malley also occasionally performed on the show, creating several re-occurring characters, such as "Anniversary Guy", "Stink Mouth PigMan", and "Gørbøn Hausinfrud".[11][12]
Since 2016, O'Malley has also frequently posted videos on his YouTube channel, similar to his Vine work.[14][15][16] In 2023, he began pay-per-view selling his videos on his own website Endorphin Port.[17]
Style of comedy
O'Malley's videos have shown him playing a manic and aggressive persona with loose thoughts, often displaying a comically overzealous interest in politics and popular culture. His Vines, uploaded until the site was defunct, showed him confronting drivers on the street and talking to them in non-sequiturs,[18] and his Twitter videos have included increasingly chaotic and demanding vlogs, such as a series jokingly directed toward presidential candidates Howard Schultz and Beto O'Rourke.[19]
Shane Ryan, writing for Paste, said O'Malley's comedy expresses "anger and envy and a sort of perverted worship of wealth and the American dream".[20] O'Malley has also published comedy videos on YouTube that have satirized InfoWars,[21]South by Southwest[22] and the AVN Awards.[23] Chloe Lizotte, writing for Reverse Shot, compared O'Malley's work to Adam Curtis and said that his videos "mock the idea that commercial entertainment could stand in for political action or fill a spiritual void."[24]
