I'm trying to think of self-deprecating comedians who are successful with it. Joan Rivers comes to mind. Phyllis Diller and Don Knotts, too. Woody Allen might also be an example, but all the self-deprecation in the world will not make him seem like anything but an arrogant asshole.

I consider a certain degree of self-deprecation to be important when you're introducing yourself. Because approaching a person requires a certain degree of arrogance. You walk up to someone and strike up a conversation, which assumes that the person had even a slight interest in knowing you.

Excellent advice, Amy. You explain the importance of a bit of self-deprecating humor, but you also point out the dangers of going overboard.

It can also make other people uncomfortable. You might meet someone who wants to be your friend, but if all you do is put yourself down, it's going to make them uneasy.

Go milk a pirate!

Agreed, Patrick (and Amy). Listening to someone talk about how much he sucks is as much of a turnoff as listening to him talk about how great he is. You don't have to be movie star gorgeous to pull off self-deprecating humor, but you do have to have confidence. Phyllis Diller and Don Knotts were not ever going to top anyone's list of most attractive celebrities, but they were engaging (and funny as all hell, too).

I'm trying to make a call but the telephone pole is all out of milk.

You're trying to think of successful self-deprecating comedians, and you forget about me? No respect, I tell ya! I get no respect at all!

What's interesting about Patrick's observation is that all of the comedians he named are from the 1960s, with Woody Allen a few years later than the others. I'm struggling to think of a a comedian since them who got anywhere with self-deprecating humor. Jerry Seinfeld, to an extent. Can't come up with any successful ones since then. What does that say about the differences in our society then vs. now?

Rodney, whoever you are, that was absolutely brilliant!

Cousin Dave, I suppose you have a point. But on the other hand, they did have staying power that lasted for decades and still went strong. It's not as if self-deprecating humor suddenly went out of vogue and Don Knotts, Phyllis Diller and Joan Rivers (and yes, you, too, Rodney) went out of style.

Of course the only one that's still with us is Joan. And even that's debatable in her case.

Sam Kinison did, to an extent. How about Bobcat Goldthwaite?

It's somewhat hard to find someone who is up-to-the minute...not because self-deprecating comedians no longer exist, but because comedians no longer exist.

What passes for comedy today just isn't funny. I've mentioned him before but I consider soi-disant comedians such as Ben Stiller and Adam Sandler to be sign of just where comedy has sunk to. These people aren't funny; they're just gross. There's no sense of wit or timing. It's just a contest to see who can be the most disgusting. Flatulence is always hilarious...if you're 12 years old.

A little known comic named Ralphie May comes to mind. He weighed close to 800 lbs at one point. He lost quite a bit of weight, but still obese. So, he said, "Don't applaud. I lost an entire fat guy and I'm still fat as hell."

When you're engaging in self-deprecating humor, you're also (implicitly) talking about yourself and thinking about yourself - it is a bit of a 'me me' self-analytical type of thing to do - that's perfectly fine in small amounts but could be a problem in and of itself if it's not counterbalanced with at least equal interest in the other person, e.g. asking questions about her or whatever, and listening to what she has to say about herself etc.

Also humor .. especially self-deprecating humor works best when it's least expected .. so e.g. it probably usually works better when you've just met someone, but if you do it relatively often, then when someone gets to know you it will no longer have that much of an element of surprise.

"not because self-deprecating comedians no longer exist, but because comedians no longer exist"

There are a few good comedians outside the US. I like a.o. Mitchell and Webb (e.g. in Peep Show UK), Jimmy Carr, Ricky Gervais (and Carl Pilkington etc.)

I've never noticed ladies being real impressed when I told them how much of a failure I was.

Go milk a pirate in a cow's telephone pole car.

"How about Bobcat Goldthwaite?"

That's true, and there's also Carrot Top. Somehow it seems different, though... instead of mocking themselves, they are inviting the audience to mock them. Gallagher too, sort of. Not sure what all of this means.

And I totally agree with you on guys like Adam Sandler. Shocking is trite.

But here's the thing: When you're a member of the OPU club, you've got to do something about that. You're the only one who can.

A couple of the guys I used to be in a band with, back in the day, have gained some weight, and aren't so gainfully employed. They joke about being in the OFB (Old, Fat, and Bitter) club. When they start going on too long about it, I just remind them that at least they don't have kids!

My pirate was cowed by the car's telephone pole.

Lobster, I was going to say Ricky Gervais as well. Patton Oswalt and Jim Gaffigan also came to mind. I'm not sure they specialize in that kind of humor, but it's something I pick up from them when I hear their stuff.

Funniest show ever: Drew Carey hosting "Whose Line Is It Anyway." And the regulars are all still alive: Colin Mochrie, Ryan Stiles, and Wayne Brady. All of whom exhibit at least a little self-deprecation (how could you not, in that format?).

"Ben Stiller and Adam Sandler "

Those guys haven't been considered comedians in a long ass time. They did stand up in the 90s. They're like Eddie Murphy, who used to be a great stand up but now is a comedic actor.

There are a ton of funny male comedians just not well known by most people. What we lack is another Joan Rivers, instead we got Chelsea Handler (terrible stand up).

Not to be rude, but all of these self-depreciating comedians y'all are mentioning? If you take away the fame and the fortune, no one wants to shag them. :-)