The Funniest Co-Workers on Broadway

Saying Goodbye to Caroline’s Comedy Club

Happy Holidaze, the best week of the winter! No school! No bosses at work! No new television shows! A handful of award contender films! Every day is like a frigid summer Friday! Solstice feasts and minor religious obligations! Family! Year end listicles! In Memoriams! Phish at MSG!

This is going to be the last original post of 2022, thank you all for your support and kind words this year. It’s been great getting back into the groove of writing for an audience again, and y’all have self selected as a group of good people I know, hope to know, or who know someone I know. Scrolling through my subscriber list, I’m elated at how many interesting, notable, talented, and—most critically—kind people I know. You’re all stars in an astounding and chaotic universe; I’m truly honored you keep reading my spicy takes and somber reflections week after week.

When I started out last March, I said subscription would be free forever if you subscribed early, and many hundreds of you took me up on that offer. A few dozen even offered to pay even when I told you explicitly not to; your support has mattered to me deeply. The point of a paywall was never to make money though, it was to create a publication with a small, hand-picked audience of marvelous people that I could share my truths and lies with. We’ve done that here, and it’s really fucking awesome.

It should also be noted that your ability to subscribe for the “free” tier and receive a lifetime of comped “paid” access ends on Sunday, January 1st, 2023. At that point a handful of archival posts will become public (including this one), and future posts will be published with a free preview for non-subscribers. If you’re already a subscriber you don’t need to do a thing, your access is already set. If you’re not a subscriber on January 1st though, you’ll either need to pay or receive a personal invite from an existing subscriber. More on that next year.

If you’re reading this now though then there’s still time to subscribe for free, I’m just getting started and you don’t want to miss where things go from here. For the last time in 2022, welcome on Down the Pipes.

“The last safe harbor for the truth is a comedy club.”

I don’t remember who said that and Google isn’t being particularly helpful, but having spent nearly a year working in one of the world’s most iconic comedy clubs, I can undoubtedly attest to that statement’s veracity without source. Yes, before I went to Futurism, TAO, Gawker, Mr Youth, or MTV, I answered the phones and checked guests in at Caroline’s On Broadway, a club that has long been considered a kind of comedic Grand Ole Opry in the heart of Times Square.

A few weeks ago, it was announced that after over 40 years, the club would be closing for good at the end of this month. “Rent hikes” was the stated reason, but comedy clubs are tough businesses to sustain even without Qatari landlords jacking up your rent. Like a restaurant, you only really make any money when every seat in the house is full for a series of seatings every evening. Anything less and you’re lucky to break even on your talent, to say nothing of your staff (who mostly works for tips), your hard costs, and your marketing/promotion budgets. Pair that with the fact that anyone can get an endless stream of algorithmically calibrated chuckles on their cell phone these days, and all of a sudden dingy basement comedy clubs just don’t appeal like they used to.

Comedy wasn’t always a losing proposition. Caroline’s first opened in the early 1980s when Caroline Hirsch was just an unemployed, up-and-coming NYC socialite. She first opened her cabaret in the hip but seedy Chelsea neighborhood before moving to the Seaport, and then ultimately landed in Times Square, down the block from the Wintergarden Theater.

From the start they helped build up the careers of some of the biggest names in comedy. This was the era of the 80’s comedian rockstar: Eddie Murphy, Robin Williams, Sam Kinnison, Rosie O’Donnell, Jay Leno, Jerry Seinfeld, Roseanne Barr, Bill Maher, Ellen DeGeneres, Paul Reiser, Paula Poundstone, Andy Kaufman, Andrew Dice Clay, George Carlin, and just about every SNL cast member past, present, and future. They all took the stage at Caroline’s at one point or another, and the club has been the backdrop for numerous TV shows and stand up specials ever since. Here’s one of Norm MacDonald’s first television appearances on the A&E Caroline’s Comedy Hour in 1991. And here are some clips of the roast they produced of Anthony Bourdain.

Hirsch is generally not a friendly person if you are not one of her star comics or a member of the deep-pocketed NYC donor class (I should point out, she is a prolific philanthropist and has donated many hundreds of thousands of dollars, if not millions, to charitable causes). Drew Grant did a stellar interview with her about a decade ago if you’re interested in getting deep with her. But Hirsch ran the joint day to day like an unlaughing ice queen with her stoic business partner, lover, and lawyer, the quietly intense and mildly threatening Andrew Fox.

The bosses.

Each Sunday morning at 10am I was expected to be in the phone booth answering the reservation line, often times Andrew would call at 10:02am and ask demandingly: “What are the numbers?” If I didn’t have a satisfactory answer ready, may god have mercy (at the time, 2005, reservations were still written in a large book like the one they still have at Peter Luger’s, in pencil. Tallying reservations was a manual act of arithmetic that was simple but time intensive and easy to fuck up while fielding 4 lines of phone calls).

It was inside that frigid booth I worked with insanely talented theater director (and fellow Seaford alum/my longest college roommate) Danny Gorman, Fox & Friends country songstress Rose Falcon, Chelsea Clinton’s personal maternity nurse Beth Traflet, Comedy Central rising star Christina Galston, government spokesperson and Silicon Valley whistleblower Eileen Carey, and the guy who should have been a role model for incels but instead just went on to get a bunch of tattoos (and dogs), Ray Gootz:

raygootz

A post shared by Ray Gootz (@raygootz)

That was just the group of folks I worked with in “the booth.”

The girl who got me the job, Jenn Krinsky, is one of the sharpest political communications strategists in New York, having recently worked for Eric Adams as comms director while he was Borough President. The nerdy marketing guy, Kirill Bichutsky, now goes by Slut Whisperer on Instagram and gets paid good money to pour champagne on people at nightclubs. Just before my time, Idris Elba was a weed dealing bouncer. Star Trump pool reporter and scooper of the Mark Meadows texts Hunter Walker used to be a barker, one of those guys forcefully asking if you “liked comedy” in Times Square.

Kirill, Jenn, and our drunkest bartender, Troy.

To say that the staff was wildly talented, funny, and smart is an understatement. And we were surrounded by some of the funniest, smartest, bravest comics on earth; it was only natural that we would absorb some of their wit and sense of humor. They say the best comics are “always on,” always in search of an “angle” or a “bit” in every waking moment. It’s true, it’s exhausting, and when you’re surrounded by that, you can’t help but turn on a bit too.

Case in point: Christmas Week, 2005. I was working the famed “Dave Attell Holiday Shows.” Each year during this week dating back decades, Attell has maintained a standing set of marathon shows, sometimes doing as many as three a night (with the last one starting as late as 12:30am and ending as late as 3am, at which point he’d take the staff to the bar across the street, Playwrights, where he’d do Jager shots and tell jokes until the sun came up).

The sets were never the same, maybe a few jokes would come back around but that man was just an endless pit of comedy. Working this week was like getting a master class in laughs from one of the all time greats, the shows would sell out to the gills but those of us working would squeeze into the sound booth or peer out of the kitchen to watch. I once watched him workshop the below Jäegermeister bit, hurling an endless amount of potential ideas before landing on the polished three you see below. It was one of the funniest things I’ve ever seen in my entire life, the laughter was painful.

Now this particular year, an up-and-coming comedian named Chelsea Handler was opening for him. She was probably around 30 and just starting to get some real looks by major bookers, and she was just slaying it as an opener. She was at a critical inflection point that all famous people experience, a kind of “ready to launch” moment where she just knew she was destined for greatness. She was just waiting for her ticket to get punched and she’d be selling that room out in no time.

After her sets, she’d hang out in the lobby and drink, making small talk with the staff and the other comics buzzing around hoping for a guest slot if Chelsea suddenly and mysteriously fell ill. She had very little patience for their type, the worst of them were a kind of desperate older male comic who looked down at her as something beneath them because she wasn’t as bitter or unfucked or ugly as they were. Her lack of amusement for their backhanded insults and sloppy passes was a thing of beauty, as were her acerbic rebukes.

One evening after a set littered with Katrina jokes (it was 2005, after all), she and I struck up a casual conversation across a high top while she sipped her drink in the lobby. She was effortlessly charming and witty, and we had some clever repartee about global warming that I’ve long forgotten the substance of, but I will never forget the look she flashed me when I managed to make her laugh. It was sexy and electric, we were clicking.

Our back and forth continued for some time across a few different shows and evenings, until late one night when she (somewhat drunkenly) asked, “Hey, it’s the last show of the night and you’re off the clock, where’s your drink?” It was that Gen X brand of implied consent silently offered through batted eyelashes that we just understood (or thought we understood) in those days. A flawed mating habit learned from decades of teen romance movies, where the precursor to a kiss wasn’t a conversation about yucks and yums, it was a long, speechless, circular pan shot in the rain with locked eyes and bated breaths.

It was “the look,” and I was not prepared for it.

I instinctively and immediately made a stumbling joke about not drinking at the office, she scoffed and listed out the array of drugs and alcohol the vast majority of my coworkers and bosses had been consuming all evening. I knew everyone around me was turning up or turning off, but the bosses knew something about me that Chelsea didn’t:

I was profoundly, deeply underaged.

Everyone else was allowed to drink at Caroline’s, but not those of us who were under 21. Their liquor license was everything, and they weren’t about to lose it over one of their minimum wage employees trying to fuck an opener.

Stumbling further as I clumsily rejected her advance, I sheepishly told her I wasn’t old enough to drink yet.

At first she thought I was joking, I was 6’1” and smart, I think she thought I was probably 23 or 24, maybe. But I wasn’t. I told her was “18…turning 19 in the spring,” and she proclaimed “YOU’RE A TEENAGER!” loud enough for everyone within earshot to realize what was going on. And just as unforgettable as her flirty look was, equally frozen in my memory is the look of disgust she had on her face when she realized I was far too young for her. Not disgusted with me, mind you. I think she was disgusted with herself for having entertained the idea. She put her hands up, backed away from the high boy we were huddled over, and said repeatedly, “This isn’t happening. This can’t happen.” It did not happen.

We exchanged messages on MySpace a few times later that year, but lost touch as her career began to skyrocket. I am and will always be a fan of her work and her sharp perspective on life (and on that note, you should listen to her on Liz Plank’s Race to 35 Podcast, she’s just as brilliant and funny as she was 17 years ago).

There are so many other absurd stories, maybe one day I’ll get my shit together and pull together a proper oral history of everything that went down in that shoddy basement. Nearly getting frostbite working in Times Square on NYE, stealing Paul Mooney’s empty Hennessy bottle from the night Richard Pryor died, seating Bo Burnham’s parents for the first time, all the drama in the back office around which comics were banned, or just shooting the shit with the great Big Jay Oakerson or the late Charlie Murphy outside of Playwrights. It’s an impossible task to collect every moment that club created of course, so many of the best stories there were personal moments of revelation between an audience and a performer. Like a retold joke that doesn’t hit the same on the second telling, you just had to be there for it.

Comedy exists in the fuzziest part of our brains, the part that understands society’s shared reality and then willingly shatters it by surfacing the infinite cracks and absurdities that underlie our daily existence. The unspoken truths we all know to be true but never say out loud, good bad and indifferent. “It’s funny because it’s true” type stuff that you couldn’t tweet in a million years, but you can almost always get away with in front of the right comedy club audience.

There’s a kind of pink elephant in the room of comedy, which is that “cancel culture” (a term I abhor) is eroding some of comedy’s pantheon. Rightly so. Bill Cosby and Louis CK are the ones who got nailed first and hardest for truly detestable behavior, but they were not alone in their misdeeds. Many were (and still are) sloppy drunks and tortured addicts, their darkness knows no bounds and lines are often crossed onstage and off.

Truly, for people who ostensibly laugh a lot, comedians are some of the darkest, most complicated people I’ve ever met. Sometimes that darkness is funny, but sometimes it’s sexist, racist, ableist, homophobic, transphobic, and ignorant. These are troubled people who have learned to turn their troubles into laughs, and sometimes that means going too far or missing the mark on a point. Some of them are just plain cruel and ignorant, and they’ve built an audience to match.

Even with those literal clowns stirring up controversy after controversy, the fact that a place exists where the perceived absurdities of our world can be interrogated, deconstructed, and poked at in front of a laughing public is a great thing. If comedy ceases to offend, then comedy ceases to exist. Not because all comedy is offensive, but for any comedy to matter it’s important that a space exists for such material to get workshopped safely. In fact, having worked in concert venues, night clubs, restaurants, and comedy clubs, it was comedy clubs that always had the most diverse audiences. It was generally a space to laugh at our perceived differences and struggles, not a place to hurt people with hate.

As George Carlin once said (paraphrasing), people are vulnerable when they laugh. We convulse, we gasp for air, we weep, we flail, we fall over. The noises we make when we laugh are often all it takes to make others laugh along with us. It is infectious, and it is medicine.

In that moment of involuntary spasm and pure joy, we are susceptible to having our minds changed. We are laughing because we see the world differently for a brief moment, but those absurd ideas often stick with society like modern philosophy. The jokes transcend us, and our view of the world may never be the same.

So farewell, Caroline’s. You taught me so much about New York, comedy, the entertainment business, and you’ve given me some of the greatest lifelong friends and philosophies I could ever hope for.

Last week, a small group of us old timers went back for the last time. After close, we did karaoke on stage, stole some glassware and t-shirts, lifted some busted table tops that were going in the trash, and had one last nightcap at Playwrights in the rain.

Comedy isn’t dying…if anything, there are more brilliant comics on the internet now than we ever had space for at Caroline’s. But the IRL spaces where comedy gets worked out in real time are going the way of the NYC pay phone, and I just hope everyone here can make some time to show up and pay for jokes (with a 2 drink minimum) while you still can.

Until next year!