20 Seriously Dark Anthony Jeselnik Jokes That’ll Twist Your Brain Sideways

The success of Anthony Jeselnik’s Comedy Central show, The Jeselnik Offensive, has vaulted the comedian into the Hollywood limelight. But for the past decade, the Pittsburgh native has been challenging norms and pushing boundaries with a litany of clever one-liners that often include a signature sociopathic twist.

The character Jeselnik has cultivated on stage has most certainly ruffled some feathers, but there’s no denying former Fallon writer’s talent and commitment to exploring taboo subjects. Jeselnik has been quoted as saying “I try to say the worst thing you could and get away with it…once people get that I’m saying awful things for a reason, it takes away that barrier. It gets them to laugh about domestic violence or breast cancer.”

If there’s any man that can turn anything into a joke, might be Jeselnik. Let’s take a look at some of his finest:

The Jeselnik Offensive
The Jeselnik Offensive

1. I’ve spent the past two years looking for my ex-girlfriend’s killer… but no one will do it.

2. My dad was a complicated man. He was a huge racist, my dad, but he still tried to be a good father, you know? Like, he would tell me that Santa Claus was black — that way, when I found out he didn’t exist, it wouldn’t be that big a let down.
3. Yesterday I accidentally hit a little kid with my car. It wasn’t serious — nobody saw me.
4. I once went on a date with a girl where we went hiking… and she gets bit by a snake in between her toes, and I had to suck out the poison… so she’s dead.
5. My mom’s been having a hard time lately. She just found out that she has to have both of her breasts removed — if she’s ever going to be good at golf.
6. I’m not a religious person; I would call myself an atheist. I don’t have a good story behind it, I’m just reasonable.
7. My great grandmother threw herself in front of a bus. The police tried to say she was committed suicide but the family knew she was just trying to stop civil rights.
8. My ex-girlfriend owned a parakeet…oh my god, that f**king thing would never shut up. But the bird was cool.
9. She got really mad a month ago, because she had e-mailed me a naked picture of herself — which is a nice thing to do — but then I messed up, and I accidentally forwarded that e-mail to both of my parents. Now, my girlfriend is furious, mortified, but I don’t even care, ’cause now I have to call up my mother and say ‘Mom, I am so sorry — that picture was just for dad.’
10. My sister just had a baby, a little newborn. The kid is adorable, so cute. She wouldn’t let me hold him, she refuses. She says, ‘No way, Anthony, I’m afraid you’re gonna drop him.’ I’m 32 years old. Like I’m some kind of idiot. Like I don’t have a million other ways to hurt that baby.
11. Whenever I meet a pretty girl, the first thing I look for is intelligence; because if she doesn’t have that, then she’s mine.
12. A couple of months ago, I gave my girlfriend some fancy lingerie, and she actually got mad at me. She said, ‘Anthony, I think this is more of a gift for you than it is for me.’ And I said, ‘If you want to get technical, it was originally a gift for my last girlfriend.’
13. We just found out my little brother has a peanut allergy, which is very serious I know. But still I feel like my parents are totally overreacting — they caught me eating a tiny little bag of airline peanuts and they kicked me out of his funeral.
14. I’ve got a kid in Africa that I feed, that I clothe, that I school, that I inoculate for 75 cents a day. Which is practically nothing compared to what it cost to send him there.
15. My mom, for most of her life, was a Holocaust denier. And it was terrible for the entire family to have to deal with until, finally, a couple years ago, we had an intervention. And we had a rabbi come into the home, had him walk her through the history of the Jewish people, and then he made her watch “Schindler’s List.” And after that, my mom did a complete 180. Now she can’t believe it only happened once.
16. I’m working on a screenplay about a guy who teaches a retarded kid to read. It’s good. But it is so fucking long.
17. My girlfriend makes me want to be a better person — so I can get a better girlfriend.
18. When I finished high school I wanted to take all my graduation money and buy myself a motorcycle. Buy my mom said no. See, she had a brother who died in a horrible motorcycle accident when he was 18. And I could just have his motorcycle.
19. Who do you think was smarter, Jesus or Buddha? I mean, just in terms of not letting themselves get crucified.
20. You don’t know anything about pain until you’ve seen your own baby drowned in a tub… and you definitely don’t know anything about how to wash a baby.

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