Dick Masterson

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Dick Masterson is America's Wingman and the host of The Dick Show. Formerly he was the co-host of The Biggest Problem in The Universe. He is infamous for his 2007 appearance on Dr. Phil where he taught the world that Men Are Better Than Women.

Dick Masterson
Dick Masterson
Dick at a Trump rally
Residence Los Angeles, CA
Nationality 50% Mexican
Other names America's Wingman, Peen Weenerstein, The 20 Million Dollar Man
Known for The Dick Show, The Biggest Problem in the Universe, Men Are Better Than Women
Title America's Wingman
Political party Libertarian
Website menarebetterthanwomen.com

Dick's celebrity surged throughout the course of Biggest Problem, where he gradually became the fan-favorite host. After the show ended, Dick started his own podcsat called The Dick Show—it's funnier, more successful, and more lucrative than Maddox's dumb show. The Dick Show is ranked 72nd overall on Patreon, with over $20K in earnings per month.[1]

Official Titles

America's Wingman

Power level


Affiliated with

First appeared

Smells like

Printing Paper


Dick can be described as a lovable yet slightly irritable puckish peeping Tom. Dick's typically Alpha male persona conceals a more understanding fatherly side, and he will often take the weak under his nurturing wing.

Dick was probably a cow farmer before his book Men Are Better Than Women was released, launching his career and taking him off of the cow farm. Dick was still relatively unknown until he met Maddox, the infamous blogger of the 90's. Maddox asked Dick to be his co-host on a podcast called The Biggest Problem in the Universe, and Dick accepted.
Dick also works with his long-time friend Sean the Audio Engineer with whom he went to school and from whom he purchased drugs. The two of them have a powerful platonic relationship together. The duo once slept together at a gay hotel and not once did they look at each others' penises, for when the opportunity arose they would close their eyes. Some fans speculate, however, that Dick and Sean may have feelings for one another, as most platonic men aren't too squeamish about seeing another man's ding dong. One has to wonder, if Dick or Sean saw each others' Peen Weinerstein, might they fall in love?

Dick is a lover of his Truck Big Betty who has underwent many modifications over the years including, but not limited to, Fast and Furious 7 branded Persian Racing Rims. Maddox feud, and an end to The Biggest Problem In The Universe. Due to tensions rising beneath the surface, TBPITU took a two week hiatus wherein, on each Tuesday, a clip show was released instead of the regular show. Following this, a final episode was released on the third week, for which Dick was not present or even mentioned. Many fans were outraged, upset, and felt left in the rain. This singular act is what caused the mysterious entity known as "The Goss Engine" to flare into life, bringing all sorts of discussion and speculation as to what happened to the show and the whereabouts of the beloved Dick.
In Episode 18 on the Dick Show it was finally revealed by Dick himself that the show ended due to Maddox seeing Dick leave with his ex-girlfriend from a wedding they both attended. It is widely speculated that Dick had sex with this girl and may have impregnated her. Due to this occurrence Maddox eventually ended the Biggest Problem and neglected any mention of Dick, thereby confirming Maddox's status as King Cuck.

The Dickheads

Dick's fans are affectionately referred to as Dickheads. If you listen to the show, you can count yourself among them. They are a creative bunch, frequently posting music, art, animations, stories, you name it. The Dickheads are among the many reasons The Dick Show took off the way it did, with Dickheads surging to support Dick's Patreon at a moment's notice. One could attribute the tidal wave of outreach to complete radio silence regarding Dick on Maddox's part. Whatever the reason, Dick, with the help of The Dickheads, has turned his beef with a blubbering Armenian pussy into a comfy place to live. Long live the Dick.

What makes them a rage?

  • Maddox
  • Neil deGrasse Tyson
  • Dr Phil's Fat Girl Audience member
  • That blonde woman who shrieked at Dick during Dr. Phil
  • David Clegg
  • Hillary Clinton
  • UCB comedians
  • Angelo's mom
  • Angelo
  • Elon Musk
  • Team Snapchat
  • Government you can see
  • Basically everything just watch or listen to the goddamn show

Powers and abilities

  • Small face phyisology: Dick is well known for having a very small face. It's ridiclous.
  • Attractive male: Goes without saying.
  • Unstumpibility field: After intense shitposting, Dick unlocked a lesser form of Trumps unstumbility power. This makes him immune to stumping.
  • Dick vs Dick: Dick is able to state two contradictory facts, while both being true.
  • Red pill phyisology: Is redpilled, making him able to see things for what they really are. He wasn't yet ascended to the realm of blackpill.
  • Reverse T-rex physiology: T-rexes have big legs and small arms. Dick has the opposite.
  • Lesser love manipulation: Uses various powerful techniques as "What's your dad like" and "I like your shoes". Works all the time.
  • Follows only 1 person on Twitter: Donald Trump.

Other Appearances

Random Factoids

  • Episode_5 - Dick has a picture of Ronald Reagan as the background image on his iPad at all times