Dick Masterson

Also known as: Dick, Dax Herrera, Dax, Dick M., The Dick

Dax Herrera created the Dick Masterson persona in the mid-2000s as a satirical take on over-the-top male chauvinism. The character debuted on the website menarebetterthanwomen.com, which catalogued absurd arguments for male superiority written with enough deadpan conviction to blur the line between satire and sincerity. The act reached its peak visibility in 2007-2008 when Masterson appeared on Dr. Phil's show, sitting in a panel of genuinely prejudiced people while playing his character to the hilt. The clip went massively viral, with most viewers unable to tell he was joking. Simon & Schuster published his book 'Men Are Better Than Women' in 2008, riding the wave of notoriety into mainstream bookstores. Masterson's podcasting career began in 2014 when he and George 'Maddox' Ouzounian launched The Biggest Problem in the Universe. The format was simple -- each host brought a problem, listeners voted on which was bigger -- but the chemistry between the cerebral, contrarian Masterson and the combative Maddox made it one of the most popular comedy podcasts of its era. The show ran for roughly 100 episodes before imploding in 2016. The falling out was rooted in personal conflict: Masterson had dated Maddox's ex-girlfriend, a transgression Maddox could not forgive. Maddox ended the show abruptly, pointedly thanking everyone who had worked on it except his co-host. What followed was one of the strangest legal battles in internet history. Masterson launched The Dick Show in 2016 as a spiritual successor, bringing audio engineer Sean (known simply as 'Shawn' or 'Sean' to fans) alon

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Dick Masterson highlights

  • Dr. Phil and the Book (2007-2008): Dick Masterson appears on Dr. Phil playing a hyper-exaggerated misogynist character promoting his satirical book 'Men Are Better Than Women.' The clip goes viral, with most viewers unable to distinguish the satire from genuine bigotry. Simon & Schuster publishes the book in 2008, cementing his notoriety.
  • The Biggest Problem in the Universe (2014-2016): Masterson and Maddox launch a comedy podcast where each host brings a problem for listeners to vote on. The show becomes one of the most popular comedy podcasts of its era, running for roughly 100 episodes before imploding over personal conflict -- Masterson had dated Maddox's ex-girlfriend.
  • The Dick Show Launch (2016-Present): After the Biggest Problem breakup, Masterson launches his own weekly podcast focused on listener-submitted 'rages' and contrarian commentary. The show quickly surpasses its predecessor in audience and Patreon revenue, becoming one of the top-earning comedy podcasts on the platform.
  • The Lolsuit (2017-2018): Maddox files a $380 million lawsuit against Masterson, Patreon, comedian Asterios Kokkinos, and others, alleging harassment and defamation. The complaint is so poorly constructed it becomes an internet comedy event. The suit is dismissed with prejudice in 2018, effectively ending Maddox's online career.
  • Biggest Problem Reboot (2022-Present): Masterson reclaims The Biggest Problem in the Universe format with new co-host Vito Gesualdi, continuing the debate-style show that made his podcasting name. The reboot carries on the original's confrontational energy with a new dynamic.
  • Dabbleverse Crossovers (Ongoing): Dick Masterson and Karl Hamburger build an extensive collaborative relationship through over a dozen WATP/Dick Show crossover episodes, shared live appearances, and roundtable discussions covering Stuttering John, Aaron Imholte, and other Dabbleverse subjects.

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