2000–2008: Reality television

Von appeared on MTV's Road Rules: Maximum Velocity Tour in 2000 at age nineteen. 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.^[20] Von faced controversy on the show for his views, including stating in the casting special that he was against interracial dating, an opinion he defended to the LSU newspaper after the show aired.^[20]

Von was on four seasons of MTV's reality game show The Challenge (formerly known as Real World/Road Rules Challenge), a combined spinoff of MTV's The Real World and Road Rules. He was a part of the cast of Battle of the Seasons (2002), The Gauntlet (2003–2004), Battle of the Sexes II (2004–2005), and Fresh Meat (2006). Von was runner-up in 2002, and was the winner of the following two seasons.^[21]

In 2006, Von competed on season 4 of Last Comic Standing, not making it to the main finals, but winning the companion online competition Last Comic Downloaded.^[22]

In mid-2008, Von was a member of the Comedy Central sketch/competition show Reality Bites Back. He won the show, beating fellow comedians, including Amy Schumer, Bert Kreischer, and Tiffany Haddish.

2012–present: game show host and acting

Beginning in 2011, Von took over as host of the Yahoo! online TV recap show Primetime in No Time.^[23][24] He hosted the TBS hidden camera show Deal With It (executive produced by Howie Mandel) for its run of three seasons (2013–2014).^[25] During this period, Von began appearing in cameo acting roles on select television shows, including Inside Amy Schumer and Why? with Hannibal Buress. 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.^[26]

In the spring of 2018, Von's three-episode scripted comedy show Man Up was released on Comedy Central, in which he attempted to improve the 'spiraling' lives of male comics.^[27] 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.^[26][28]

2011–2015: Early ventures

In April 2011, Von began his first podcast, The Comedy Sideshow. Taped at the Improv Comedy Club in Hollywood, Von interviewed comedians and other entertainers. The show had 23 episodes, the last of which premiered in November of that year.^[41]

In 2015, Von started a weekly podcast with filmmaker and journalist Matthew Cole Weiss called Allegedly with Theo Von & Matthew Cole Weiss. 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. The podcast lasted three years and had a total of 123 episodes.^[42]

2016–present: This Past Weekend and King and The Sting

Von began a new podcast, This Past Weekend, in December 2016. This long-form video podcast features storytelling, answering fan voicemails, and guest interviews.^[43] He released his 200th episode in May 2019.^[44]

In December 2018, Von and fellow podcaster/comedian Brendan Schaub started a podcast called King and The Sting. At the podcast's release, it debuted at number 1 on the iTunes Podcast charts in the US and also reached the top charts in the United Kingdom, Canada, Spain, and Australia.^[45]

In January 2022, Schaub and Von added a third host, Chris D'Elia, to King and The Sting, renaming it King and The Sting and Wing.^[46] During this time Von began taking breaks from the podcast, allowing guest hosts to fill in. On November 4, 2022, King and The Sting and Wing was officially renamed The Golden Hour, with Workaholics actor Erik Griffin replacing Von.^[47]

In September 2023, Von publicly accused Kast Media and its CEO Colin Thomson of non-payment, after pro wrestling personality and podcaster Jim Cornette had made similar claims about Kast and Thomson in July. 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.^{[48][49][50][51][52]}

In August 2024, Von interviewed US senator Bernie Sanders, as well as US president and then-nominee Donald Trump.^[53][54] In October 2024, he interviewed US senator and future vice president JD Vance.^[55]

In July 2025, Von was named to Time magazine's inaugural "TIME100 Creators" list - the publication's roster of the 100 most influential digital voices - appearing in the "Leaders" category for his podcast This Past Weekend.^[56]