Content warning: The following text describes domestic violence and can be disturbing and/or triggering for some readers. Please find resources listed at the bottom of the article.

“You probably aren’t gonna like this one. Or have I already told you this? The one about O.J.?”

“No…maybe. Remind me.”

"White women who like it rough in bed will be the death of me.”

“I remember. I mean I still think that’s pretty funny.”

“Yeah, I think it is, but I’ve gotten some bad feedback. I’ve met more people who have liked that joke than not, but those who don’t like it are often white women because they’re the butt of that joke.”

I’m a white woman; the joke didn’t really phase me, but I knew what he meant.

“One girl said she didn’t like abuse against her kind. Violence against women. That’s one of the jokes in which, like, if you’re mad about that joke, I understand. But I do get upset because I feel like people get—not weirded out, but more caught off–guard when they see me onstage telling dark jokes.”

His phone lights up, and he glances briefly at the screen, furrows his brow, but quickly unfurrows it and looks back up.

“If I was an awkward, straight, white male, then it would make sense to the audience that I tell those jokes, but the fact that I’m the complete opposite of that, and I’m onstage telling these dark jokes about morbid things, makes some people think, ‘What are you talking about, this isn’t your field,’ and that’s the barrier I’m trying to break.”

His full name is Jonathan Hudson Webb II.

“Not ‘junior,’” he’ll add, as he’s named after his father. “I hate that shit.” 

He’s from the north side of Chicago. Not north north, he’ll clarify, more middle–north. He attended the same high school—Whitney Young—as Michelle Obama, Craig Robinson, and the Wachowski sisters who directed The Matrix. He remembers his time there quite fondly as a popular, athletic, and academically gifted student.

His bildungsroman narrative, which was complete by the time he graduated the eighth grade, concluded by gifting him with a fully intact personality, genuine confidence, and a stark lack of fucks to give about what people thought of him. Objectively, that’s a rare mindset for a thirteen–year–old.

Jonathan began studying at Penn in the fall of 2019 as an economics major. His success was nearly instantaneous and quantifiable. Blackstone, the alternative investment firm and distributor of one of the most coveted internships for ambitious business students, offered him a summer position before the end of his first semester. 

But that isn’t his Plan A career. It’s his stepping stone to become financially stable enough to pursue stand–up comedy full time.

“It’s more of a realistic thing,” he says. “For me to get this amazing degree and just be like, ‘Alright, now I’m going to go around to open mics until someone grabs me,’ is such a bullshit white man story.”

“What’re your thoughts on the American dream?”

“It’s literally just fictitious. It’s a fictitious, dangerous concept,” Jonathan says. “I think the American dream is kind of, like, a Manifest Destiny façade. These white men were just like ‘We’re gonna do this thing now.’ It’s kinda funny.”


Jonathan smiles. 

“White people do so much shit that they kinda kill themselves over doing. Like doing blackface. Some of them got, like, skin disease over that. Y’all were really trying so hard to make this very racial epithet, but now you’re getting skin disease over it? That’s fuckin’ hilarious.”

Jonathan has one tattoo. He wants a second (something to pay homage to his home city of Chicago) but his mother, whom he describes as a very traditional Southern lady, has told him that even a Jesus tattoo wouldn’t make her happy.

His ink is a quote from the poem “Invictus” by William Ernest Henry. It reminds him constantly and permanently of his responsibility to own, cultivate, and never deny his individuality. The poem also has heavy historical significance: Nelson Mandela read it to other prisoners during his incarceration at Robben Island prison, and Barack Obama read it at Mandela’s memorial service in 2013.

The tattoo reads, "I am the master of my fate, I am the captain of my soul."

“Being a Black comic, I’ve definitely made jokes in front of white audiences that they didn’t understand about the Black community or  Black people in general, but I’ve told them in front of Black audiences and they’re like ‘Oh, that’s funny, I understood that joke.’”

I nod.

“There’s one thing that really annoys me, though, when I’m with mixed audiences where there’s a lot of white people, even my friends. I’ll tell a certain joke and I’ll notice that all the white people won’t laugh, and, like, all of the people of color will.”

His voice gets somewhat deeper, as if he’s matching the weight of his tone with that which the subject carries for him.

“I’ll ask my friends later if they didn’t like the joke or if they don’t get it and they’ll say they thought it was really funny, but they just feel bad for laughing. And, I don’t know, that really annoys me.”

The comedy that Jonathan produces is meant to be funny yet also provocative, but not for controversy’s own sake. He wants people to think.

“Just because you don’t laugh at a joke, you’re not a better person. Like, you can be a completely shitty person and still not laugh at a joke. You’re at a comedy show to be entertained and if you are entertained it doesn’t really help when you’re sitting there blank–faced, pretending…”

He trails off.

After three application attempts, Jonathan was admitted to Penn as a transfer student from Morehouse College in Atlanta. He credits his second rejection as the catalyst for his comedy performance career.

“When I was considering transferring, I looked at all these schools and spent months working on applications,” he says. “I applied to seven schools, and I got into zero of them. I’d built an application that I was really proud of, and to hear back from all seven—nope, nope, nope, nope—it was hard.”

Comedy had been a hobby since high school, but performances only began at what Jonathan refers to as his lowest point following such severe rejection.

“Fuck it,” he told himself. “You have nothing else to lose.”

He was out of place at his first open mic, a single comic surrounded by the solemnity of spoken word poets. The host told him bluntly before his performance that should his set tank within a couple of minutes, he’d be kicked offstage.

“I just went up there, I did my thing, and I felt so comfortable,” Jonathan says. “I felt like I found something in my life that I really wanted to discipline myself to work on.”

The weather that night was sharp. The air was cold and still and clear in a way that made lights in faraway buildings look like individual, miniature high beams that split the cloudless sky above. The house I’m supposed to enter thrums in the way that college functions normally do. I predict a mildly sticky floor and at least four direct fire code violations.

It’s 9:30 p.m. on a Friday night in December of 2019 and as soon as I step over the mail–littered threshold of a stranger’s home I am presented with a choice: Natural Light Beer or Yerba Mate. 

Yerba Mate, obviously. 

I nurse the tea in silence. Meanwhile, Jonathan has managed to finesse himself a first–in–line spot in the queue of stand–up performers. That’s not unexpected. He likes going first: it sets the standard, and people will remember him. He’s pretty memorable regardless. His charisma is aggressive. He is wearing all black except for his sneakers. His shirt says “London” on it.

Jonathan is introduced to the audience by the host. He starts his set by shooting the shit, riffing off of the audience’s knee–jerk reaction to his presence. He’s gauging them, testing the waters. Then he launches into his first bit.

“Thanksgiving. It’s a really weird time for me. It’s hard to navigate around your family.”

Nods of agreement flit across the audience. I’m perched on the staircase, at the back of the living room slash seating area slash stage, doing a shit job of recording the performance on my phone camera.

“It’s like, yeah, you want to spend time with your family, but there’s that one family member that’s two drinks away from telling you that all lives matter because a high schooler in the neighborhood died from trying to vape a Lysol can.”

The joke lands. I try to hold my phone still as I watch the audience suck the juice out of menthol JUUL pods and pass around a single THC pen attached to a keychain. Jonathan puts his right hand over his mouth and nose and pretends to inhale imaginary Lysol by snorting forcefully. He puts on his best white boy drawl. 

“Fock! This shit’s fockin hard, brah! Bleuugh, aw, fock!”

He switches to a deadpan of his normal voice, flavored with a shit–eating grin.

“And then he died.”

The silence breaks.

Reach–A–Peer Hotline: 215-573-2727 (every day from 9 p.m. to 1 a.m.), a peer hotline to provide peer support, information, and referrals to Penn students.

Penn Violence Prevention: 3539 Locust Walk (Office Hours: 9 am – 5 pm), (215) 746-2642, Jessica Mertz (Director of Student Sexual Violence Prevention, Education), Read the Penn Violence Prevention resource guide. 

Public Safety Special Services: Trained personnel offer crisis intervention, accompaniment to legal and medical proceedings, options counseling and advocacy, and linkages to other community resources.

Penn Women's Center: 3643 Locust Walk (Office Hours 9:30 am – 5:30 pm Monday–Thursday, 9:30 am – 5 pm Friday), PWC provides confidential crisis and options counseling.