After Road Rules, Von competed on three seasons of its spin-off show, Real World/Road Rules Challenge, the last one in 2005. In 2006, he appeared on season 4 of NBC's Last Comic Standing, winning the title of Last Comic Downloaded. In the summer of 2008, Von was cast in Comedy Central's Reality Bites Back, a one-season series where a cast of comedians improvise their way through faux reality show episodes. Also cast were Donnell Rawlings, Bert Kreischer, Amy Schumer, Mo Mandel and Chris Fairbanks. The series was hosted by Michael Ian Black. In 2009, Von created crank texting"" (Crank texting may be defined as sending a text message to random phone numbers to incite conversations), and began his crank texting blog, www.cranktexts.com, which was picked up as a column by College Humor a year later. In 2012 Von became the host of Yahoo's TV recap show, Primetime in No Time, the most watched daily show on the internet, replacing former host Frank Nicotero. His 2012 'The Half Hour' premiered on Comedy Central in June 2012, and he acted in his first film, InAPPropriate Comedy, which hit theaters in March 2013. In the summer of 2013, Von hosted the new TBS hidden camera show Deal With It, executive produced by Howie Mandel.[2] The show was picked up for its 2nd season in early 2014, and a second installment of its 2nd season, schedule to shoot in the Fall of 2014. Von has also been seen on The Arsenio Hall Show, Hello Ross, Chelsea Lately and Watch What Happens Live. Theo began hosting This Past Weekend, an advice podcast, in 2016. That same year, his first one-hour comedy special Theo Von: No Offense premiered on Netflix. Theo recently debuted his album 30lb Bag of Hamster Bones, which became the No. 1 iTunes Comedy Album..

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