He auditioned for the show at an open casting call for The Real World and Road Rules at a bar while studying at Louisiana State University.

He won the show, beating fellow comedians, including Amy Schumer, Bert Kreischer, and Tiffany Haddish.

[26][27] He hosted the TBS hidden camera show Deal With It (executive produced by Howie Mandel) for its run of three seasons (2013–2014).

[28] During this period, Von began appearing in cameo acting roles on select television shows, including Inside Amy Schumer and Why?

He has said that he was not more interested in acting earlier on — despite having opportunities to do pilots and sitcoms — because he was not very enthused about the projects offered at the time and because they often conflicted with his touring and podcasting schedules.

[30] In August 2019, Von announced that he had been cast in the big-budget film The Tomorrow War (at the time known as Ghost Draft), and had been recruited for the project by its lead actor, Chris Pratt; a few weeks later, Von announced on his podcast that he had dropped out of the movie due to the time commitment required.

[32][33] According to Von, he had difficulty as an entertainer in Hollywood, as talent agents viewed him as a former reality TV star and were thus skeptical about giving him work as a comedian.

[35] Von achieved one of his first major comedic accomplishments a few years later, in 2006, when he won the title of Fan Favorite on the online competition aligned with the fourth season of Last Comic Standing.

He has been a recurring guest on many comedians' podcasts, including The Joe Rogan Experience, Joey Diaz's The Church of What's Happening Now, The Fighter and the Kid, Bobby Lee's TigerBelly,[27] and The Adam Carolla Show.

The two friends, whose styles and presentation contrasted, competed to see who had better "alleged" tales of celebrities, hilarity, trauma, dating, success, and failure from their years living in Hollywood.

On November 4, 2022, King and The Sting and Wing was officially renamed The Golden Hour, with Workaholics actor Erik Griffin replacing Von.

Corresponding accusations were also made by Jason Ellis, Brendan Schaub, Bryan Callen, Whitney Cummings, and Alyx Weiss, each of whom stated they were owed money by Kast Media, including several six-figure and seven-figure shortages.

It was reported that Kast Media was in the process of being acquired by PodcastOne and that in lieu of full payment, Thomson offered creators partial compensation combined with stock options.

Amid the news, LiveOne and PodcastOne stock dropped considerably and the company no longer planned to officially hire Thomson.