The 5 Worst Wingmen In Modern History

5. Chewbacca

“Chewy” cockblocked Han Solo back and forth across the entire galaxy.  Besides being over 7 feet tall and hairy, Chewbacca couldn’t speak one word of English, and he had a horrible temper.

At least he could back you up in a fight, and he most likely had a huge shlong.


And by the way, this isn’t that first time that Harrison Ford had a horrible wingman:



4. Magic Johnson

Lets just say he won’t be “taking one for the team” anytime soon.

“But Captain Power, Magic Johnson is rich and famous.  Are you Positive that you don’t want him as a wingman?”

“I’m HIV-Positive that I don’t want him for a wingman.”


3. Beavis

“He he he.” With one of the most annoying laughs of all time, Beavis is the 3rd worst wingman in modern history.  To be honest, I never thought that Butthead was a bad looking guy (no homo),  and he definitely had some decent “game.”  Butthead should have gotten rid of this loser a long time ago.  I couldn’t get laid in high school either, so I used to stay up all night watching these guys on television. (Notice that they are in Washington D.C.)

What a surprise! They are in Washington DC

2. Hitler

My grandfather spent 3 years in Europe looking for this asshole.  Can you imagine going into a bar with his guy? Besides being probably the worst human being in modern history, he is also one ugly bastard.   I wouldn’t let him stand within 20 feet of me with that horrible moustache and comb over.

Was he gay? Who knows.  But he must have been somebody’s wingman in his early 20’s at the German Beer halls.


1. Paul from “The Wonder Years”


This guy was the worst wingman ever! I watched his best friend Kevin Arnold chase Winnie Copper around for five straight seasons!  His best friend had the worst case of “one-itis” in television history, and Paul didn’t do anything to stop it.  In almost every episode Paul was in the background bitching and complaining to Kevin, and being a total cockblocker.   He was always wearing  horrible clothes and his ugly glasses, and he was constantly blowing his nose because of his allergies.

Congratulations Paul!  You are the worst wingman in modern history!

Read More: The World Is A Cock Blocker

26 thoughts on “The 5 Worst Wingmen In Modern History”

    1. Bonus gina tingles for mentioning you want women to be paid for child rearing by taking the money out of the defense budget.

  1. ““Chewy” cockblocked Han Solo back and forth across the entire galaxy”
    That first line alone made me lose my shit.

  2. Wasnt Hitler engaged with Eva Braun ? Most German women would’ve spread their legs wide open for Hitler, as sad as this can be, that was the reality back then.

      1. Exactly.
        I would not want Hitler as a wingman because of the genocidal asshole that he was, but skags went for him big time. He is definitely proof positive that having a moral compass is literally not required to get with women. If you have power thats all females want, period. And it won’t mater to her that the lampshade in the dining room is made of human skin.

  3. I always imagined that Ernie was surfing on seismic waves of hot college tail while Bert chastised him about, “keeping the noise down if you’re going to use the room tonight,” or, “why won’t you just settle down with one of them?”

  4. The manosphere talks about having a knack or a gimick like being a DJ or newspaper columnist that passively attract girls. I think Hitler had a pretty solid gimmick as the man gunning for world domination which trickled into his body language giving him charisma.

    1. Either that, or he would show up to your girlfriend’s house and say “Bang me or else”..
      Mussolini had numerous mistresses (like most italians), Hitler was a little strange to say the least…

  5. Hitler had a lot of affairs with married women, and led a lot of rich German women on to gain their support and wealth. He was a very naughty boy.

  6. Bitches dug the Fuhrer for the same reason they dig all alpha-males: Because he walked it like he talked it. He didn’t stand around staring at his thumbs and spitting bullshit game about modern art or how to get admitted to nursing school; he called it like he saw it, went outside, and got it the fuck on. Whether you agree with his policies, or Mao’s, or Stalin’s, or Genghis Khan’s doesn’t matter.
    Bitches respect resolve. And whether its flaking on a date, tattoos, or national policy, women will swear up and down they want someone middle-of-the-road and low-key, but its the guy who wades in up to his neck and says “fuck you, i’ll do it my way” that gets more ass than he can carry.
    But the tiny mustache does have to go…

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