[5] His mother, Jenny Henderson, founded the musical duo Syn Twister with her twin sister Jude Hammock.
[10] Both his mother and father battled with substance addiction; whereas Whit ultimately achieved sobriety, Jenny succumbed to complications arising from her alcoholism in 2009.
[11] Having moved to Los Angeles, he was joined by his childhood friends from Gulf Shores, Alabama: Clay Tatum and Jeramy Ritchie.
[12] The trio joined forces with their new roommates, Budd Diaz and Rodney Berry, to form the comedy troupe Power Violence.
[12] Thomas and his associates screened self-produced comedy videos and performed original bits featuring elaborate props and stunts.
Thomas's Tom DeLonge impression, an intrinsic part of his act, was featured on the Put Your Hands Together and the You Made It Weird with Pete Holmes podcasts.
They were produced in response to Tom Papa's #LiveFromHome challenge for quarantined comedians;[20] Thomas was nominated to participate by his friend Rory Scovel.
[7] Thomas performed at the Lounge in honour of his aunt and late mother, whose new wave duo Syn Twister behaved as the house band and local celebrities.
[2] The special concerns Thomas's early life in Alabama, the emotional arc of which centres on the redemption of his absent father Whit.
[9] Thomas also mines various childhood traumas for laughs, such as his failed abduction, the death of his mother, and the subsequent estrangement of his aunt.
[6] "Hurts to Be Alive" and "The Golden One", the lyrics of which were directly lifted from Thomas's early hardships, have received particular critical attention.
[11] The hour-long recording was co-directed by Thomas and Tatum; among its executive producers are Bo Burnham, Christopher Storer, Olivia Gerke, and Ravi Nandan and Inman Young for A24.
[3] Individual music videos for "Partied to Death", "Dancing with My Dad" and "Dumb in Love" have been uploaded to Thomas's YouTube account.
[25] The six-track EP was produced by Melina Duterte (Jay Som),[25] and features contributions from Christian Lee Hutson and Al Menne of Great Grandpa.
[26] 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.
[29] 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.