Take a dive into Gladstone’s comedy pain pool.

The 4 Greatest Things in Comedy (Everyone Misunderstands)

#4. Seemingly Politically Incorrect Jokes That Are Totally Fine

I do love jokes that aren’t afraid of offending. You can fracture and deconstruct stereotypes in a way that dances with hatred without embracing it. For example, there is such a thing as a non-homophobic gay joke. I’ve always loved this one, and I stand by it as being completely appropriate:

Q: How do you tell if your roommate is gay?
A: His cock tastes like shit.

The joke does not mock gays or gay sex practices. It’s a joke about misdirection. The humor comes from the notion that some dude would be blowing his roommate in an earnest attempt to find out if he’s gay. Still, I’m sure it’s upsetting to the politically correct.

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He got so fucked over for that weed smoking; I will say that. That was ridiculous. Holy shit.They caught him smoking weed. They treated him like they caught him shooting heroin into the soft spot of a preemie baby’s head, you know? It’s fucking WEED. “It sends the wrong signal.” Yeah, it tells kids: “You can smoke a little weed and still be the greatest swimmer in the history of mankind.” Although, could you imagine- could you imagine the size of the bong hits Michael Phelps must take? HOLY shit, talk about bowl-clearing lung capacity. You do not want to be sharing your weed with Michael Phelps.
—  Greg Giraldo: Midlife Vices
Everybody thought that Titanic was the most romantic movie ever. A story about two teenagers who knew each other for three days. Try to make that movie with a couple that’s been together for a few years. ‘Get in the goddamn boat, Rose!’ 'I don’t wanna get in the boat!’ 'Get in, come on, I’m freezing my ass off out here! I wanted to go to Jamaica, but no, we had to go on a cruise in the middle of the winter!’ 'You never draw me naked anymore…’
—  Greg Giraldo
I tried to get on the plane and the woman said I was too drunk to get on the plane. Too drunk! Do you know how shitfaced you have to be!? For someone to say “Sir… you are just too drunk to sit in a seat.”
—  Greg Giraldo

50 Favorite Comedians: Greg Giraldo

This one homeless guy came up to me the other day, and he was asking me for money. I was about to give it to him, and then I thought, ‘He’s just gonna use it on drugs or alcohol.’ And then I thought, 'That’s what I’m gonna use it on. Who am I to judge the guy, really?’

(Pictured: Me, Giraldo and Chappelle in 1997ish)

Anonymous asked you:
Ur twitter is awesome, do u worry ur wasting stand up material on us fucks? I’m a lowly open mic comic and even I worry about that. cheers @lesterdiamond28

Call me old fashioned, but I don’t see any audience seeing my comedy as “fucks.” Also, I can still do it in my stand-up if I did it on twitter. In fact, I have a few jokes in my act now that started as tweets. Even if you have a lot of followers, only a handful of people see each tweet, so it’s not that big a deal, you fuck.

askkneesockssan asked you:
Neal: What was your biggest arguing point during your time working with Mr. Chappelle, if you two had any at all? He always painted your relationship rather well.

The biggest arguing points were more about logistics: him being late all the time or procrastinating to the point of danger. Also, he went to Africa there at the end. That was a pretty big arguing point. Matter of fact, we didn’t even talk for a few years after that, it was such a big arguing point.

Anonymous asked you:
Ever Meet the late comedian Greg Giraldo?

I knew Greg from the time he did open mics. Gonna find a picture from the time we was all young…hold on.

-Neal Brennan

Submit your questions for Neal Brennan here. Neal Brennan: The Half Hour premieres Friday at 11:30/10:30c.

Because I went to Harvard Law School it seemed like I had my shit together, but I did only because it’s not hard. Everyone is so self motivated that they leave you alone. You get study outlines and just cram, but then when you get out into the real world, it gets tricky. Most comedians are people who couldn’t really work in the real world, they’re too disorganized, too lazy, too fucked up, too erratic, too unstable. If you could work in the real world you would have stayed there because it is so many years of misery in comedy before you really start popping