Can't Believe You're Happy Here and The Older I Get The Funnier I Was (2022–)
March 2022 saw the release of Thomas's EP, Can't Believe You're Happy Here, on Hardly Art Records. The six-track EP was produced by Melina Duterte (Jay Som), and features contributions from Christian Lee Hutson and Al Menne of Great Grandpa. The release of Can't Believe You're Happy Here coincided with a music video for "Don't Have A Cow", which was uploaded to YouTube. Raphael Helfand of The Fader noted that "the record sounds crisp and clean while maintaining a distinctly DIY undercurrent".
Can't Believe You're Happy Here is a folk record that engages with themes of toxic masculinity, self-doubt and existentialism. Thomas notes that the EP was informed by numerous influences, including self-reflection precipitated by the COVID-19 pandemic, YouTube countdown lists, and his friendship with Hutson.
Thomas's second album, The Older I Get The Funnier I Was, was released on October 21, 2022. As with the preceding Can't Believe You're Happy Here EP, the record was produced by Melina Duterte. Other contributors to the record include Al Menne, Christian Lee Hutson, and Harrison Whitford.
A music video was released for the lead single, "Rigmarole", in August 2022. Thomas has explained that the song is about "trying to shake depression with routine and ultimately accepting I've got no choice but to sink into it". According to Pitchfork, the remaining songs on the album explore themes like Thomas's people-pleasing tendencies and relationship with his father.
Thomas toured North America with Al Menne in support of The Older I Get The Funnier I Was. Thomas also performed a new stand-up routine, Big Baby, at the Elysian Theater in Los Angeles throughout the final quarter of 2022. The show featured stories and songs lifted from Thomas's youth, and also engaged with concepts of loneliness, insecurity and Christopher Nolan's The Dark Knight trilogy. Alternative comedian Conner O'Malley performed as Thomas's opening act.
Thomas also appeared in numerous films and television series in the early 2020s. He played substantive roles in Am I OK?, a comedy drama that premiered at the 2022 Sundance Film Festival, and Clay Tatum's supernatural comedy The Civil Dead. Thomas has been confirmed to appear in two 2023 television series: Slip and #1 Happy Family USA.
HBO released Whitmer Thomas: Terminal Crew of Dudes to HBO Max on August 14th, 2026. He performs with the titular backing band consisting of his brother, Johnny, and his close friends with whom he grew up skateboarding. Along with original songs, Thomas delves into stories involving his bandmates and relates the experience of being a grown adult that still skateboards.