How Did Theo Von Get So Popular?

How did a comedian from St. Tammany Parish, Louisiana become a household name across the country, and how the hell is Theo Von descended from Polish royalty?

Twenty-five years ago, MTV cast Theodor Capitani von Kurnatowski III for the ninth season of their reality show Road Rules, setting him on a winding path to stardom that no other Road Rules or Real World alumnus could match. While many veterans of the late 1990s, early aughts dawn of reality TV have turned their early appearances on television into respectable entertainment careers, no one else who got their start in the early days of reality TV can say that the President and Vice President are guests on their podcast besides Von, especially after they let it slip that they’re opposed to interracial dating.

Today, Von is one of the biggest names in all of entertainment, and his meteoric rise to the top of American popular culture may seem like an anomaly to anyone who didn’t follow minor MTV stars past the turn of the millennium, but if recent history has taught us anything, it’s that the road to power runs through reality TV.

Von was born in Covington, Louisiana in 1980 to Gina Capitani and Roland Theodor Achilles von Kurnatowski, a 68-year-old immigrant from Nicaragua who traced his lineage back to a powerful noble family in Poland. Following what Von described as a “low-income” childhood, he briefly attended Louisiana State University in Baton Rouge, where he auditioned for both The Real World and Road Rules at a local bar. Von landed his spot in the latter show's ninth season, the Maximum Velocity Tour, where he traveled across the country with five strangers while Rainn Wilson fed them unique challenges.

Following his stint on Road Rules, Von returned to Louisiana State, where he had to defend some of his controversial comments on the show regarding the topic of race mixing. During one interview on Road Rules, Von expressed his opposition to miscegenation, saying that Black people and white people shouldn’t mix, and he stood by his stance in an interview with the Cal Poly Mustang. Said Von, “I’m not a fan of interracial dating. I don’t hate black people. I don’t hate Asian people. I don’t hate anyone. I’m just chillin’.”

Then, at 23, Von decided to continue his momentum from Road Rules and move to Los Angeles to pursue comedy. While building up his stand-up career, Von continued to appear on MTV shows such as The Challenge, The Gauntlet, Battle of the Sexes II and Fresh Meat, but he quickly found that the comedy world was less likely to take him seriously the more he established himself as a reality TV star. Finally, in his big comedic break, he combined his two branching career paths with a successful performance in the 2006 season of Last Comic Standing, where he won the fan-voted online competition Last Comic Downloaded.

From there, Von’s job opportunities in the comedy business began to increase, and he ended up winning a comedy/competition show called Reality Bites. Von also began to tour internationally as a stand-up comedian, including multiple USO shows, one of which was, bizarrely, at Guantanamo Bay. By the early 2010s, Von was becoming a staple of stand-up on TV, earning a featured set on Comedy Central Events and performing on various late-night shows. Around that same time, Von found his true love and biggest moneymaker: podcasting.

In 2011, when Von first broke into the emerging podcast industry, he hosted a series called The Comedy Sideshow, in which he interviewed fellow comics at the Improv Comedy Club in Hollywood. While Von’s stand-up career would take up most of his time over the following years, in 2016, he launched the most successful project of his career, the ongoing podcast This Past Weekend w/ Theo Von where he now interviews some of the most powerful people in the world. Through his connections with other podcasting giants like Joe Rogan and the since disgraced Chris D’Elia, Von was on the vanguard of the podcast explosion that propelled him and his contemporaries to the top of comedy, for better or for worse.

Today, Von’s reality TV years may seem like a distant memory, but, without Road Rules, there’s a good chance that Von never lands the Netflix deals, he never becomes one of the biggest podcasters on the planet and he never talks to President Donald Trump about how cocaine makes him feel like an owl.

In that universe, Von also never shoots his shot and gets rejected by Jess Sims live on College GameDay, either. But, then again, that also wouldn’t have happened if Sims were Black.