By Josh Gondelman — 20 Oct 2025

#154. D'Angelo and You

Is this too sensual a photo for a eulogy-type newsletter?

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Hi everyone,

Last week was eventful in that I attended many events, not that anything especially seismic occurred during any of them. On Wednesday, Maris and I went with our friend Emily to see the first night of previews for Chess on Broadway. I realized on the way there that I had no idea what Chess was about and whether it was good. (Maris told me "chess" and "I don't know.") The story was compelling and the performances were very good (Great voices on those Broadway stars! Who knew?), but the politics of this revival were a little confusing to me. I also wish there had been a little more dancing, which is weird because I do not know anything about dancing. Overall, we had a great time!

Chess playbill in front of a blurry stage. — I wouldn't stop singing "CHESS!" like "Jet" by Wings.

I also got to celebrate the launch of Adam Pally's new HBO special An Intimate Evening With Adam Pally. I got to open for Adam up in Providence while he was working this show out, and it's really weird and fun. The two of us had a great car ride up and back for the gig, and you don't really get much of that in the special, except he did use one little joke I pitched to him while we were on the road.

Poster for Adam Pally's comedy special. — And an intimate evening it was.

On Saturday, Maris and I went to the Great Community Bake Sale in Manhattan's Financial District. A hundred or so of New York City's best bakers/pastry chefs donated their time and effort, selling a wild variety of snacks. Excellent pal Natasha Pickowicz has been running this event for years, raising over $200,000 for charity. We picked up a bunch of baked goods (I had to! It was for a good cause!) including an EXTREMELY good Snickers Eclair. I am finishing up a little (terrific) piece of lemon bundt cake as I write this newsletter. IF YOU ARE INTRIGUED BY THIS NEWS, Natasha has written a cook book about dessert and has one about hot pot on the way!

Baked goods and a baked good do gooder (Natasha).

Because of the event's immense popularity, the line outside took a while to creep through. Well, for several minutes after we got there, it stood entirely still on the orders of the fire department. I am not usually one to stand in long lines for Saturday morning food experiences, but it was a beautiful day, and it was for charity, so what was I going to do? Outside of the knowledge that we were waiting, the experience was indistinguishable from just hanging out in lovely weather.

The folks doing line control were comedian friends who were, to put it gently, a little overwhelmed. A few people in line complained to them about the line-ness of it all, which on one hand I understand. Complaining is one of the great gifts afforded to us during our brief time on this planet. But complaining to the people in charge of an event when they obviously can't do anything about it...that's no good. You aren't helping anything, and you're making everyone more flustered.

A premise I come back to a lot is that sometimes things are annoying, and it's fine. Sometimes there's traffic. Sometimes the sandwich you bought at the airport feels all limp and sweaty like it just came out of a sauna. Sometimes your upstairs neighbor spends three years practicing "City Of Stars" from La La Land on the piano. And guess what? It's fine. It will be good LATER. Now it's A PAIN IN THE NECK. Grow up, that's how the world works.

This is a message from me to me as the project that Leiby (who was also one of the line-managers) and I have been working on for a year seems like it might be kaput. When I got the news, I felt bad. I stomped around. I complained via text message to several friends. And then eighteen hours later when I felt normal and not deranged anymore, I texted again to say that the situation is still bad, but also I am fine. Bad and fine can coexist. In fact, sometimes it's important for you to allow them to. (When they started letting people into the bake sale again, it ruled, and people were so happy to get to eat lots of good food in exchange for their donated money. Often, annoying turns into good if you just chill for a minute or two.)

Sometimes, of course, things are bad and not fine. Longtime newsletter readers may remember that Maris and I missed the last big No Kings protest because we went to a Brooklyn location that wasn't especially populous or energetic. This time we missed it because of a bake sale (FOR CHARITY! Some people were taking action in the streets, and some people were doing it with the treats!), but I felt hopeful seeing the pictures of teeming, dissatisfied masses congregating to show their displeasure with ~looks around~ the way things are. I hope everyone who protested finds a day-to-day or at least month-to-month way to channel their frustration into even more concrete action. But it's good to get together and affirm that some things that are bad are not fine and indeed must be changed through effort and organization.

Over the course of the week, I also did a bunch of standup and popped into a friend's birthday celebration and took a long walk with another buddy. Maggie the Pug met my friend Hannah's baby, but he's not my baby so I will not post a picture.

THIS WEEKEND I'm doing four shows at Sports Drink in New Orleans! Come by and hear my new jokes if you're in town!

Flyer for my 10/24-10/25 shows at Sports Drink. — See you there, New Orleans!

A FEW WORDS ABOUT D'ANGELO

This isn't a pep talk so much as it is a little remembrance of an artist whose work meant a lot to me! It's my newsletter, so I can do that. R.I.P D'Angelo.

In 2014, I was working at Last Week Tonight with John Oliver, a dream job that I eventually left for another dream job. As part of a bit written by Will Tracy if I remember correctly, the show was looking to book a famous r&b singer. Someone in the office (I think it was me?) suggested reaching out to D'Angelo. John (Oliver) replied immediately: "Perfect! He lives in Philly and he's STILL GOT IT!" D'Angelo's team politely declined our show's offer. He was gearing up to tour (!!!) and didn't feel like he was in shape for public appearances.

Obviously, the standards for D'Angelo "being in shape" (physically) were set by his video for "Untitled (How Does It Feel)" a four and a half minute reinvention of the Kinsey Scale. If you could watch the clip and not think DAMN! then you were officially not attracted to men. The pressure of being a sex symbol in the wake of this video famously contributed to the slow process of D'Angelo writing and recording new music. On his follow-up album, he addresses this pressure in the song "Back To The Future Pt. 1." "If you're wondering about the shape I'm in/I hope it ain't my abdomen you're referring to."

So maybe by "in shape" his reps meant he wasn't quite mentally ready to be perceived yet. Which is, of course, fair. He had no obligation to do a silly comedy bit if he wasn't up for it. But between news of an upcoming tour and rumblings (also from John Oliver) that Questlove had been zipping out to Philly for recording sessions at night after wrapping his days at The Tonight Show, I felt hopeful he'd be putting out new music soon.

When D'Angelo released Black Messiah – his first record in nearly a decade and a half – in the middle of the night on December 15th, 2014, I listened to it twice in a row. Black Messiah runs just under an hour, but it feels longer, vaster. The songs take their time, winding their way in and out of the listeners ears. It's tender and anguished and righteous, sometimes by turns and sometimes all at once. His voice is beautiful, but flexible, asserting itself where it fits compositionally on each track. There are grooves that make you think how??!? It's so fucking good. It's the last album D'Angelo ever put out.

When D'Angelo announced his live dates in support of Black Messiah, I whiffed on tickets to his show at The Apollo. But I was able to wrangle passes to his SNL appearance through a friend who worked at the show. Thanks (I THINK) Jake!!! It was one of the cooler things I've ever witnessed. I linked above to the performance of "Really Love" from that night. It takes a second for the camera to find him once the song starts. He saunters to the mic from amidst the band. Extremely in control. Nothing rushed, as was his custom.

Maris and I also got to see D'Angelo perform at the Roots Picnic in Bryant Park in 2016, although co-headliner John Mayer's set took up a litttttle too much of the evening. Even then, nearly a decade ago, we had the sense that we might get the opportunity to see him play music in person again.

The tragedy of someone dying is that they're dead, not that they're no longer producing work. And no artist owes the public an expansive catalog. Still, it's hard to see an artist die so young and not wonder if they had more art they wanted to create. The hard part about taking the time to make impeccable music is that you don't always end up with that much of it. The good part about it is that it's great and will live forever.

I did not know D'Angelo, but I hope that his later years brought him peace. He didn't owe us anything more than he gave us. We owed him more than what we gave him in return. I've been listening to Voodoo and Black Messiah especially all week. It's a gift to get to hear music made by an artist (artists, really) who cared so much about saying what they had to say when they had to say it.

PEP TALK FOR A READER

I fleshed out this pep talk request with just a few extra words to make it feel just a touch requestier. Here goes!

May I please have a pep talk regarding being a freelance creative in a time of AI and tight purses?
- A Human, Being

Here is a confession: I am practically addicted to reading hater shit about generative AI models. I know I write about this a lot, but please trust I think about it more than that even, so I'm sparing you the bulk of my hateration (credit: Mary J. Blige) most of the time. I tear through Ed Zitron's newsletter even thought it is a little too nuts and boltsy for my comprehension level about the financials of some of these big companies, not to mention too technical about computing power and the cloud. I relish every viral post highlighting a mistake in a Google search AI summary. Like when they say to cook pizza dough by warming it up under your armpit or that Steven Seagal is the President of Lithuania. I scroll through the vicious replies every time Sam Altman makes some kind of inane, unverifiable claim about his company and an interviewer acts like a toddler whose "nose" has been "gotched" by a fun uncle.

I do not feel bad about this hateitude because the people who make these products hate us. They want us to stop talking to each other and thinking about each other. They want to replace writers and artists with software that can't even do our jobs. It's like if the self checkout at the grocery store occasionally told you that bananas cost $80 for a bunch (not true yet despite the tariffs) or that Le Sueur canned peas could cure athlete's foot. If that were happening on the regular, nobody would go: "But look at how well those machines scan the rest of the time!" They would rightfully say: "This sucks ass! Make it stop!"

When I read about the water usage of every ChatGPT query, it makes me wish some karmic force would take a "smoke the whole pack" attitude towards these companies' data centers and wipe them out with a flood.

But the simple fact that you are right and generative AI models (not to mention the tight purses of every institution with cash on hand) are wrong is scant comfort when you have bills to pay, and the places where you used to look for money no longer feel compelled to provide a useful product or even have employees. I do think we will outlast this hype cycle. Most people don't want to have garbage piped down their throats through a tube. Or, not this garbage at least. You truly must have the body of an adult human and the brain of a starfish to be enduringly amused by the ability to, let's say, create a video of yourself having diarrhea out of an airplane onto a crowd of protestors.

People want to read and watch and listen to work made by other people. Is this opinion influenced by thinking a lot about D'Angelo this week? For sure. But still, I believe that thinking, feeling humans want to date and kiss each other instead of setting up a bot to talk to another bot and then watch The Office all alone on whatever streamer owns it now while the bots fall in love.

Despite the voices of ten loud rich guys and a thousand losers in Patagonia vests who only go outside long enough to get into a Waymo on the way to the "company" they "founded" that's just one room in a WeWork, nobody else believes it when they say shit like: "My autocomplete program is so fast and intelligent that it's basically a god, and because I created it we need to invent a new word for something more powerful than god. Megagod? Supergod? Wicked Good God? ChatGPT, tell me what you'd call something that is more omniscient than omniscience?" The rest of us see through this bullshit.

While we are waiting for the bubble to burst, there is no shame in doing other work than the kind of things you've rightfully felt a lot of pride in making a living from. It is painful to have to reevaluate your career path because every boss thinks you can be replaced by three spellchecks in a trench coat, but it is not embarrassing. The dignity doesn't come from the money. It comes from cultivating skills and having insights and offering something meaningful to other human beings (and sometimes animals too, but they're less dedicated readers/viewers, I imagine).

The money is for rent and snacks and pants and (unfortunately) sometimes medicine. It's not for apps that pretend to be your girlfriend or a friendly encyclopedia. And the sooner the people with more dollars in their bank accounts realize this, the better off we'll all be.

PICK-ME-UP SONG OF THE WEEK: Sadlands - "Bad Idea"

Sadlands, a band I know about because it features excellent comedy acquaintance Jess Lane (and my childhood friend Dan knows other band members too, I've learned), just put out their debut album Try To Have A Little Fun, and it's exactly what I want things to sound like. "Bad Idea" feels like it comes from the same lineage as the Beach Bunny track I posted recently, so I think this will also suit the taste of That's Marvelous readers! The chorus is catchy and easy to sing along with. The drums sound like a million of those little noisy popping dealies you'd whip at the ground (or at each other) as a kid. I love a song about being excited to take on a potentially-doomed endeavor. It's what work and life and politics feels like, and it's nice to have an anthem for enthusiasm and effort against all odds.