Born in Chicago, Illinois, U.S., on December 20, 1986, O'Malley began his comedy career at the Annoyance Theatre, where he met his future wife, Aidy Bryant. When Aidy was cast onSNL, 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. 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. 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". In addition to writing for Late Night, O'Malley has also written for Joe Pera Talks with You, which he also co-starred in as Joe's neighbor Mike Melsky, and the 66th Primetime Emmy Awards. As an actor, O'Malley has been featured in several television shows, most notably Detroiters, where he played Trevor, Tim's free-wheeling brother, and Horace and Pete, where he played Eric, the boyfriend of Horace's daughter. O'Malley has also appeared on Broad City, and Netflix's , and has been a recurring guest on The Chris Gethard Show since 2013. In 2019, he appeared on I Think You Should Leave with Tim Robinson. Since 2016, O'Malley has also frequently posted videos on his YouTube channel, which have since gained media attention similar to his Vine work.
Style of comedy
O'Malley's style of comedy in the 2010s, especially on his main social media outlets, Vine, YouTube, and Twitter, has led to his videos becoming viral. O'Malley's videos have shown him playing a manic and aggressive persona with loose thoughts. His Vines, uploaded until the site was defunct, showed him confronting drivers on the street and talking to them in non-sequiturs, and his Twitter videos have included a series of increasingly chaotic and demanding vlogs directed toward presidential candidates Howard Schultz and Beto O'Rourke that have been compared to performance art. 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". An unofficial compilation of his Vines uploaded onto YouTube in 2015 proclaims that they "tell the story of a man very publicly and very loudly slipping into a state of shattered, bewildered madness before being reborn in the desert as some type of disoriented creature". O'Malley has also published comedy videos on YouTube that have satirized InfoWars, South by Southwest and the AVN Awards.
