By Josh Gondelman — 27 Oct 2025

#155. The Mob and You

Chauncey Billups, more like Chauncey Payups, more like it. Allegedly.

Perhaps I can interest you in a free subscription or a paid one? I do this newsletter largely for fun, but there's a little cost to maintain it, plus I have an expensive year-round iced coffee habit.

Hi everyone,

I'm writing from New Orleans where I've spent the weekend with Maris. While in town I had great shows (at Sports Drink, one of my favorite venues), excellent food, and a cold. It rained so much on Sunday that I didn't have to feel bad for wanting to lay low rather than going on a haunted alligator tour or attending a jazz parade. For real though, thank you to Sports Drink for having me back! It's always fun to perform for the crowds in their cozy venue, and to hang out in the Big Easy as opposed to the Massively Difficult, where I live.

I ate some vegetables too, but they were less visually dynamic.

So many of the little restaurants in the neighborhood by the venue had impeccable reviews online, and I couldn't tell whether they were actually going to be good, or whether people in New Orleans are generally having a nice time and grade on a curve. But they all ended up being terrific, even though one night we wandered into a place with a Halloween Tasting Menu (?) where all the other customers were dressed up as witches. The staff had spent so much effort creating names and descriptions for the signature cocktails that I truly did not have the energy (a cold, remember?) to parse the offerings, so I just got a soda water.

It did feel a little bit like hanging out there eating salads and drinking soft drinks in our regular, non-costume clothes was a sit-in against the dark arts. Remember how weirdos used to protest Harry Potter because the books promoted the occult? Isn't it wild that those folks were ahead of the curve on hating J.K. Rowling, but for the stupidest possible reasons? Ultimately, I don't think we dampened anyone's Halloween enthusiasm too much.

I am going to try and be a little briefer than usual this week (famous first words), but I also want to shout out my friend Natalie Walker's cabaret show Mad Scenes, which we saw last week at Joe's Pub. Natalie has maybe the best singing voice of any performer I've ever seen live. And her brain is a folio of intense women and their onscreen mental breakdowns, which she used as jumping off points for the various movements of the show. Mad Scenes is so specific to Natalie's taste and talent and vision, and seeing her perform it to a sold out crowd was a real highlight of my week on its own, and it was also a perfect reminder that you can just do the creative project you want to do the most, even if you fear it might just be for an audience of only you. Probably other people will like it too! (It helps if you're upsettingly talented like Natalie, but that's not a prerequisite for making art!)

I'll be on Wait Wait this weekend (spoiler alert?) so look/listen out for that. Plus if you're in Brooklyn and would like some minimally festive Halloween fun, Alison Leiby and I are once again hosting a Sup, Bro? (Sup, BOO?) show at Union Hall on 10/31! It's early this time! 7:30pm! And this edition will feature Isabel Hagen, Mark Little, Jenny Tian, and Natasha Vaynblat. Other special guests maybe? But these guests are special enough, imo!

Plus, just planning ahead a couple of weeks, I'm performing on a 25th anniversary show for Jesse Thorn's Bullseye with an absolutely incredible lineup. It's 11/15 at The PIT in NYC, and it'll be a blast.

Graphic for 11/15 Bullseye 25th Anniversary show featuring me, Tony Shaloub, H. Jon Benjamin, Jad Abumrad, and Kristen Anderson Lopez/Bobby Lopez. — I wasn't lying about the lineup!!!

And, at the end of the year, I'm going to be in the Pacific Northwest for a few shows. On 12/28 I'll be in Seattle at the Crocodile. It's the biggest venue I've ever headlined in Seattle, and I'd love to see you there! It's right around the corner from Here-After, where I've been my last few times in town, but it's the larger main room. I can't wait! I'll be in Portland at Helium on 12/30 and 12/31, but the ticket link for those shows isn't live yet.

ANOTHER FUN LITTLE THING

As I alluded to in September, I got to shoot a segment with GBH's Curiosity Desk while I was in Massachusetts. Thank you to Joanie for inviting me along for the ride and Edgar for being a great host and the whole team for being a dream to work with. It was a great day and I am psyched about how it all turned out.

It was an honor to participate in the Curiosity Desk Roast Beef Tour of the North Shore. Roast beef sandwiches are sacred, and the culture around them is terrifying. I'm still a little nervous that the members of a private roast beef sandwich rating Facebook group will tear me apart and sous vide my flesh, but I hope I did them proud. I did refer to a sandwich that brought me back to my childhood as "Proust Beef" so just for that I am pretty sure they will want to kick my ass.

(Oh also, after an appropriate period of mourning and a bunch of poking around online, I also found the video a few college friends and I made about twelve years ago, recreating the D'Angelo "Untitled (How Does It Feel)" video with me as Shirtless Geraldo Rivera as D'Angelo. Watch it if you dare.)

PEP TALK FOR THE MOB

By Erik Drost - Chauncey Billups — I know he is not technically IN the mob, but he is the person in this story least likely to have me murdered.

Many readers of this newsletter are not sports-type people, so some of you may have missed this fascinating story, but I do think it's interesting enough to learn a few of the details. Last week, Portland Trailblazers head coach Chauncey Billups was indicted as part of an FBI investigation into high stakes poker games allegedly rigged by the mafia to allegedly steal money from rich gamblers allegedly. Billups, it is alleged, was the bait (impressive celebrity) used to reel in the fish (wealthy marks). These fish were – according to the FBI – gutted (my word for "defrauded" because I wanted to extend the metaphor a little further) through various means of cheating including: markings on cards that were visible to people wearing special glasses or contact lenses, hidden cameras in players' chip trays, and an x-ray table.

Now! While I don't condone organized crime, I want to reiterate for a seventh or eighth time that these allegations have not been proven and all accused parties remain legally innocent until proven guilty. BUT, if these accusations are true...this is kind of a cool scheme. I do not believe that anyone participating in an illicit card game automatically deserves to be swindled out of gobs and/or wad of cash. Although if you were, hypothetically, to commit this kind of deception, an extremely impressive way to do it would be through contact lens-based subterfuge and and a card table that can also tell you whether your femur is broken. Which, you know, is not out of the question in a situation like this alleged scenario.

Not to mentions, I'm kind of dazzled by the idea that these whales (which are not the same as fish, biologically, I understand) were supposedly lured in by an NBA coach who has (to put it gently) never succeeded at that job and whose playing career inarguably peaked in 2004. That means that the mob (SHOULD THESE ALLEGATIONS PROVE TRUE) was ahead of the curve on identifying the allure of millennial early-century nostalgia. I would have loved to hear a low ranking mafia associate say to an acquaintance/accomplice: "This guy thinks he's going to come in here and take our money? Well call him Zooey Deschanel because that's just adorkable."

I am certainly not affirming that these acts happened in the way that law enforcement suggests. And I'm definitely not besmirching the good names of any possible members of the family. What I am saying, is that if these events did happen to transpire in accordance with the descriptions in the indictments, they would have been kind of awesome. Good job, the mob. Allegedly. (Assuming this story doesn't get way, way darker.)

PEP TALK FOR A READER

I appended the nickname to this pep talk request. Otherwise I'm running it basically as-was.

I recently moved to a brand new city in a different continent to pursue my creative dreams. HELP!
- Moving and Quaking

This first part might sound a little loopy, but stick with me here: Sometimes the thing isn't really the thing. Sorry to sound like a fortune cookie, but I will explain. You are neck deep in the journey/destination dialectic, and from where you are it might be hard to tease apart which is which. You might not know for a while.

I know this is a little woo woo coming from a writer whose normal prose is more like "sandwiches taste good" and "please buy tickets to see me talk about my parents' email address at Jokies in Skokie." I am not an especially spiritual person, despite having a pair of socks that I am convinced are unlucky and another pair that I think are lucky. I can't find the second of those pairs, which feels like the basis for a country song, but that's neither here nor there.

I don't doubt that you'll need some assistance with your intercontinental transition. But I don't think it's with the big existential stuff. For SURE there will be some linguistic hiccups even if you're just shifting from English (American) to English (Classic or Other). You'll need new charging cables for your electronic devices, or maybe just adapters for a while, until you see how the move sticks.

But the big intrapersonal issues with a long-distance move in pursuit of creative fulfillment can fortunately/unfortunately only be resolved through time and effort. Will you have short-term trouble adjusting to your new home? Maybe. Will your creative pursuits succeed beyond your wildest dreams? It's possible. Will that success cause you to innovate new, even wilder dreams? Could be.

That's not the important stuff though. I mean it is, but it's not what you have to worry about. It'll all happen or it won't. What matters is that you are building a life in a way that is exciting to you. (And hopefully that you're being good to the people around you as you work on your own stuff.) If it all turns out exactly as you hope, hell yeah. If there are hiccups and you have to regroup and redirect, that's also okay. Legacy is a myth. The enduring power of William Shakespeare's work is not useful to William Shakespeare, a dead guy...or dead woman...or dead composite of several writers. You get it.

How the thing turns out is less important than the fact that you are doing it. You are making an effort to concretize your dreams into experiences. You've taken a giant step towards converting hopes into facts. Things might end up more wonderful than you'd ever imagined. Or less. Or different entirely. But you are living your life in the best way you know how, and you don't need my help to do it.

PICK-ME-UP SONG OF THE WEEK:
Tame Impala - "Piece of Heaven"

I always forget that Tame Impala is a Very Big Band, and I think it's because I rarely see Kevin Parker (Mr. Impala) doing celebrity stuff. But it's also because Tame Impala's music sounds so well suited to headphones. You forget that other people can listen to it too. Stadiums worth of people, even. I, at least, am like: "Oh this is the song that I do a little dance to while I wash dishes." I lose track of the fact that basically everyone has to wash a dish or two sometimes, and they also need music to do a little dance to.

Deadbeat, the group/guy's new album came out a week and a half (or so) ago, and I like it, but I love this song. (Maris says Deadbeat is possibly her Album of the Year so far, so I will have to spend more time with it, not because she's making me, but so I can dig in and enjoy it even more.) It sounds like he's singing over a lost Enya track, which I wouldn't always mean as a compliment, but I very much do in this case.

I love a song about feeling content in someone else's bedroom or being excited that for someone to visit your bedroom (Carly Rae Jepsen, "I Want You In My Room"). It's an extraordinarily feel-good song that's not too much. It's just the right amount. A piece of heaven, if you will.