[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.

[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".

[18] Filmed in Brooklyn, the special received critical acclaim upon its release, with Tim Marcin of Mashable describing it as "a scathing critique of our AI reality" and Clare Martin of Paste calling it a "fever dream, frantically reflecting our own overwhelming, tumultuous present while still keeping us in stitches".

His Vines, uploaded until the site was defunct, showed him confronting drivers on the street and talking to them in non-sequiturs,[21] 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.

[26] 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.