A Look Back: Theo Von’s Journey From MTV Reality Star To Interviewing Trump, Cuban, and More

Screenshots via MTV/This Past Weekend

Theo Von has had a long journey from budding comedian to a podcaster interviewing everyone from President-elect Donald Trump to Mark Cuban, but few likely remember that his career started all the way back when he was just 19 on MTV reality shows.

As MTV moved away from wall-to-wall music videos, they embraced making reality television on the cheap while unscripted shows were still a relatively new concept, finding their biggest success early on with The Real World. Von was one the faces that was part of the hodgepodge of reality show contestants on the network, joining Road Rules in 2000 at just 19 years old.

Road Rules was a spinoff of The Real World and it was MTV’s second jump into the reality TV genre. The cast of six featured people between the ages of 18 and 24, all of whom lived in an RV, followed clues, and completed missions at various locations, mainly across southern states. The Office star Rainn Wilson actually played a part early on in the show as the Road Master, the show’s presenter who would give the cast mates their clues.

The show serves as a time capsule today. It debuted when reality TV is in its infancy, but Von was fairly refreshing. He was open and honest about his personal struggles with people and being emancipated at 14. Sometimes his fellow cast members didn’t really know what to make of him and his sometimes bizarre comments, but fans of him today can see the early stages of of the honest and quirky comedian and podcaster he would become.

“What the hell is Theo? That’s what I think people think of me when they first talk to me and get to know me,” Von says in a clip from the show. “They don’t really understand me because a lot of times I don’t even understand myself.”

The Louisiana native would go on to compete on multiple seasons of The Challenge (also known as Real World/Road Rules Challenge), a spinoff of both Real World and Road Rules.

The Challenge was, well, there’s really not much variation between these early MTV reality shows. They make the Real Housewives franchise feel as complex as a Christopher Nolan picture. The setup is always the same: gather a cast of young people, have them compete in various goofy challenges. The catch of The Challenge is that the cast was pulled from past competitors on The Real World and Road Rules. Not all challenges on these shows were goofy though. On Road Rules, Von and the cast had to walk between two hot air balloons on a plank, which sounds like it was taken straight from Fear Factor.

Through 2000 to 2006, Von was an MTV regular, showing off hints of the wacky, wonderful randomness that would become his standup and his This Past Weekend podcast. According to Von though, Road Rules came long before he even thought he would pursue comedy.

Von explained in a 2018 episode of the TigerBelly podcast:

I had no plans of going to comedy or being a comedian. I didn’t have any — I was just walking across campus at college and I was just like really depressed and they had auditions and next thing you know, they called me one day and they asked me to go on the trip, you know, and I was like, oh, this is going to really, really interesting and, yeah, that’s how I got into it.

Today clips of Road Rules and The Challenge are fairly hard to find, but Von likely has no problem with that as he’s explained the show presented him with some roadblocks as a comedian starting out in Los Angeles.

“It’s not hard to separate from, it’s just, like, I was so young. I’m 37 now, I was 19 then,” he said in the 2018 episode of TigerBelly.

What’s most interesting about Von’s reality TV career is how overshadowed it is by everything since. After leaving reality TV behind, Von dedicated himself to comedy. He would dabble some in competition shows like Last Comic Standing (where he won the online competition in the fourth season), but he got his biggest jump through his relationship with Joe Rogan and his guest appearances on The Joe Rogan Experience.

Von has now built himself his own podcast empire and he’s interviewed everyone from a mortician to a carnie to Trump. 2024 was a true banner year for Von as he sat down with Trump in the heat of the election, had on Vice President-elect JD Vance, billionaire Cuban, and Teamsters President Sean O’Brien. Von is able to bring an innocence and genuine curiosity to these interviews and the sometimes complex topics, which are not always best suited for comedy. His interview with Trump was one of the president-elect’s best as he got more personal than usual as the pair discussed addiction and Trump opened up about his late brother’s struggles with alcoholism.

Von made Mediaite’s Most Influential List this year for a reason, but his place in today’s culture is even more impressive when you consider how far he’s made it after starting out as just another fresh-faced teenager on MTV.