The 7 “Coolest” Losers in Comedy Movies


Losers are an important part of any movie.  When a person is down on their luck or has no will to live, watching them do things that “matter” makes the character more dramatic.  Also, it provides for a much better storyline.   I would have to say that drama movies carry this point well.  I mean just look at Rocky.

But when I think of Losers comedy movies come to mind.  But it’s not just that these people are losers.  They’re actually people you’d want to hang out with.  Most are witty.  Most are smart.  It’s just that they don’t care.  And that’s what we love about them.

Here are the seven coolest losers in comedy movies

The Dude in The Big Lebowski


The Dude abides.  He’s filled with funny wisdom.  He goes with the flow.  He gets high every day and yet somehow winds up getting laid by a ridiculously rich chick.  All the while he really just doesn’t care all that much.  Just an awesome character.

Thurgood Jenkins in Half Baked


It’s Dave Chapelle.  Do we really need an explanation?

Happy Gilmore


He may be a hockey loser.  He may lose his temper.   But the man is witty.  The man is charming.  He gets the hot chick.  He uses century old golf clubs.  He’s got a homeless caddy.  And he doesn’t even care about the money.  Happy rules.

Willie Stokes in Bad Santa


I think Billy Bob gives his finest performance out of any movie here.  This is one of the most classic comedies in the history of comedies.  I’m a huge fan of this movie and man is Willie awesome.  Talk about a guy who just doesn’t give a f*ck.  There’s simply no other way to put it.  But boy would I like to be his friend.

Ben Stone in Knocked Up


Seth Rogan’s character is a little different from the rest here.  Stone just takes it all in stride.  He’s definitely a good dude.  He’s more of an “every man” type of guy.   Like the dude you always liked to hang out with in college.

Peter Gibbons in Office Space


When your dream is to sit around and do nothing all day and you convince Jennifer Aniston to have sex with you, it’s safe to say you’re a cool loser.

Max Fischer in Rushmore


One of my favorite characters in any comedy movie.


Floyd in True Romance


I had to mention Lloyd only because of how awesome he is.  True Romance isn’t really a comedy but it’s a damned funny movie.

  • Lagrange

    I’m with Bill and Ted.

  • Candee

    Sorry to be one of those nit-picky readers, but there’s an E in Hockey. That was really bothering me.

    I can’t think of anymore Cool Losers.

    Nice list!

  • zomgmouse

    Sorry to be one of those nit-picky commenters, but in this context “any more” is two words.
    That was really bothering me.

  • IcemanD

    You gotta love Steve Carrell in 40 Year Old Virgin.

  • Lane Meyer is one of the coolest losers ever.

  • Cheryl

    I think really any classic Adam Sandler movie he was a loser…Billy Madison, The Waterboy…love Happy Gilmore tho.

    How about Will Ferrell in Old School? Frank the Tank!! Loveable loser.

  • Nattyb

    Lane Meyer! Great Call.

  • Madison

    I’m surprised you didin’t include Lane Meyer, but you more than made up for it by including Willie Stokes. Good job.

  • EJ

    Read headline, mind immediately went to Floyd. True Romance is the best movie nobody’s ever seen.

  • MacGyver1138

    Harry and Lloyd from Dumb and Dumber. They are morons, but everyone still roots for them. Also, I quote this movie on a regular basis.

  • The Dude Abides.

  • Abby

    Max Fischer is one of my all time favorite movie characters. Thanks for including him!

  • kometes

    Damone from Fast Times.

  • Awesome list, I have not seen True Romance though, that was apparently Brad Pitt’s only scene. I have seen the other movies, and they all deserve to be on that list, especially “The Dude”. Jeff Bridges is just a likable guy, even when he is playing the bad guy in a movie like Iron Man.

  • YelenaRossini

    Seymour Krelborn from Little Shop of Horrors! I can’t believe he isn’t on here!

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  • Candee


    Oh yeah. I missed that. Whoops.

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  • The Dude Abides.