When Legends Drop In – Hemispheres Magazine, May 2015

The next time you’re at a comedy club in New York or Los Angeles, don’t be surprised if Jerry Seinfeld or Chris Rock stops by for a surprise set

by Larry Getlin (originally appeared in Hemispheres Magazine, May 2015)

On a typical night in the mid-1970s at The Improv, a comedy club in the then-sketchy Hell’s Kitchen section of New York City, rookie comic Elayne Boosler would serve as the club’s door person and often get saddled with the 3 a.m. slot, stand-up’s version of paying dues.

But as a newbie, Boosler didn’t always get to do that spot, because if more famous comics dropped in unexpectedly, her set was the first to be cut. And as a new comedian at a time when places dedicated to performing comedy were rare, Boosler was bumped by the best, including Richard Pryor, Lily Tomlin, Rodney Dangerfield and Jay Leno. The strangest, though, were the nights when her time was cut so that Andy Kaufman could take the stage. At the time, he was Boosler’s live-in boyfriend.

“Not only were we in love, but he taught me everything about comedy. He’s the reason I’m a comedian,” Boosler says. “When he had something special he wanted to try, he’d apologize to me and say, ‘I don’t think you’re going to get a spot tonight. I need to do an hour.’ Of course, I understood and rooted for him.”

Not only were we in love, but he taught me everything about comedy.

So did the audience, as Boosler’s loss was their gain. And it continues to be so, as the celebrity drop-in has become a tradition, one that is enjoying a golden age. At shows throughout New York and Los Angeles, comedy fans are treated weekly to unexpected sets by the likes of Chris Rock, Dave Chappelle, Aziz Ansari, Louis CK and Jerry Seinfeld. A-list comedians use these sets to work out new material, connect with audiences in an intimate club environment and stretch their creative muscles in between larger theater shows and other show business endeavors.


The Improvisation club opened in 1963, initially show-casing singers. But within a year or so, the emphasis switched to comedy, making it the world’s first dedicated comedy club. Founder Budd Friedman has seen Milton Berle drop in at 3 a.m. and ad-lib onstage for hours, and Friedman recalls the first time he met Rodney Dangerfield, around 1964 or ’65, during that legend’s first drop-in at the club.

“He comes in for the first time, and he’s this drunk walking in at about two in the morning,” Friedman says. “He introduces himself and says, ‘I’d like to go up.’ And he bombed, because he was so drunk. He came back the next night, sober, and went onstage as if to say, ‘I’ll show these punks.’ He mopped up the room and became a regular at the Improv after that.”

As the club developed competition throughout the ’70s, drop-ins became more common. By the early ’80s, the form found a master, unsurprisingly, in Robin Williams. Bill Grundfest co-founded New York’s Comedy Cellar, known today as the primary spot for A-list drop-ins, in 1982, and recalls Williams as the first big comic to drop into the club unannounced, about a year later.

“I was onstage, emceeing,” he recalls. “In the doorway, in a yellow rain slicker, there’s this guy, and he gives me this little wave. I say to myself, ‘Holy s***, it’s Robin Williams.’ I say to the audience, ‘Our next guy has been doing very nicely. You may have seen him on several TV shows. Please welcome Robin Williams.’ The audience thought I was putting them on, and they kinda giggled. But then they see who’s walking to the stage, and there’s this collective ‘Holy s***,’ and the place just burst. For five minutes they would not stop.”

This reaction is the norm for drop-ins. When MCs announce surprise sets by superstars, there’s always a brief lull—since the crowd isn’t sure it’s not a joke—until they see the performer. Then they go wild. Sometimes the drop-in surprised even Williams himself. Caroline Hirsch, founder and owner of Carolines, recalls a night in 2006 when Jeff Garlin of “Curb Your Enthusiasm” was headlining. His “Curb” castmate Cheryl Hines was in New York promoting the movie RV, which she co-starred in with Williams, and the two came to the club to see Garlin.

“They’re watching Jeff, and somebody heckles him,” says Hirsch. “All of a sudden, from the back of the room you hear an Irish accent start to heckle the heckler. It was Robin. Jeff said to the heckler, ‘Hey, you’re no match for this guy.’ Then he introduced Robin, and Robin went onstage.”

Early on, the etiquette of the drop-in was unclear even to those who ran the clubs, as Grundfest realized the first time Jerry Seinfeld dropped into the Cellar, around 1984.

“It was during the week, and we were paying $15 a set,” he says. “I couldn’t decide if I should pay him or not. Would I insult him by not offering to pay him anything, or would I insult him by paying him $15? So I said, ‘Jerry, I feel compelled to offer you this $15.’ Under great duress and eye-rolling, and Jerry’s saying, ‘It’s completely not necessary,’ I relieved myself of the $15, which I believe found its way onto a waitress’s tray.”

Chris Mazzilli, the co-founder of New York’s Gotham Comedy Club, which has served as a favorite drop-in spot for big names since it opened in 1996, recalls how the first time Seinfeld dropped in, around 1999, his set created great buzz for the club. “This was pre–Internet boom, pre-Facebook, pre-Twitter,” says Mazzilli. “I was playing on a soccer team then, and I showed up to practice, and two guys in completely different businesses were like, ‘Hey, I heard Seinfeld was at your club last night.’ It didn’t hit the news. They just heard through word of mouth. That’s how big a deal this was.”

Sometimes, audiences are blessed with multiple drop-ins in the same show. Mazzilli recalls a night in the early aughts, when Robert Klein was doing a regular Wednesday night run at Gotham. Seinfeld and George Carlin came to see him, and both wound up taking the stage. Then, the three congregated in the club’s bar after the show, swapping stories as audience members hovered around them trying to catch every word.

“The whole [crowd] came out of the showroom and surrounded the guys. It was amazing,” says Mazzilli. “One woman started to hyperventilate. I got her a chair, and she said, ‘You know, I’m from Ohio, and things like this don’t happen in Ohio.’ I said, ‘You know what? You’re right.’”

Over the past few years, comedy and pop culture blogs have swelled with accounts of drop-ins from Rock, Chappelle, CK, Seinfeld, Jim Gaffigan, Dane Cook and many more, as at least one seems to grace a small club stage every week. The most legendary drop-in in recent times took place at the Comedy Cellar, on February 27, 2013. That night, Rock—probably the most prolific comedy dropper-in today, and such a fan of the surprise club set that he featured one as a plot point in his recent film Top Five—wowed a stunned audience with a set. Then on came Chappelle for a 45-minute drop-in. And then, Chappelle called Rock, Kevin Hart, Bill Bellamy and Marlon Wayans onstage to riff with him, pass the microphone, and share funny tales of their years of experiences with each other. While the night garnered major press coverage, including an oral history–style retelling in GQ, those kinds of magical nights are not unusual at the Cellar.

“One night, a few years ago, I had Jerry Seinfeld, Chris Rock and Ray Romano back to back, on the same show,” says Estee Adoram, the club’s longtime booker and manager. “Leaving the show, people were on their cell phones, like, ‘You’re not gonna believe what just happened.’”

Part of what makes the drop-in so special is that it’s almost entirely unique to stand-up comedy. Unlike other performing arts, such as acting or playing music, stand-up cannot be workshopped or rehearsed without an audience, so performing live is the only true way to gauge timing and feedback on a routine. Drop-ins, therefore, give A-list comedians the chance to work out new material in front of audiences that didn’t drop big bucks on tickets and baby-sitters, and therefore won’t feel cheated by a set that’s not as tight as an HBO special.

“The expectations for a set like this are completely different,” says Sean McCarthy, who runs the comedy website The Comic’s Comic. “If you’re working Radio City Music Hall or the Beacon Theatre, people have carved out their whole night to see you, and they’re coming with expectations. But if you’re dropping in and surprising them, then you have the advantage, because misdirection and surprise are at the heart of comedy.”

In fact, Adoram says that when Rock—who’ll often take the stage for drop-ins holding a yellow pad with notes for new jokes—drops into the Cellar, lowering expectations is his first order of business. “Chris starts his show, everybody’s screaming, and he says, ‘Calm down. It’s not gonna be as great as you think.’ Which, by itself, is funny.”

Given that comedians are usually trying new jokes when they drop in, these sets give crowds a chance to see stars do something they rarely do in public: fail.

“I’ve seen CK and Gaffigan drop into the Upright Citizens Brigade Theatre in New York and struggle, but they were trying new stuff,” says Adam Newman, a comedian who’s had his own half-hour special on Comedy Central and who’s been bumped at a club by Seinfeld. “So I’ve seen those guys struggle, but how great is that? It shows us that the process continues, no matter how long you’ve been in the game.”

New York Times comedy critic Jason Zinoman recalls a night he saw CK drop into a popular show called “Whiplash” at the Upright Citizens Brigade Theatre.

“When he went onstage, it was absolute pandemonium. People were going insane,” he says. “What was interesting to me was that his set wasn’t that good. It was not terrible, but he was clearly working some stuff out, and it really wasn’t working. And yet, the audience went berserk over every joke. It was fascinating to see how sometimes you can’t trust the audience, and how fame is a challenge, because CK has to figure out whether his stuff is working or not by the audience applause.”

The other side of the drop-in equation is the lesser-known comics, like Boosler in the ’70s, who get bumped for the A-listers, then have the pressure of having to follow the greats.

New York comic Sam Morril, who’s performed on “Conan,” has been bumped by Seinfeld, CK and Gaffigan, but his greatest challenge came when, at the Cellar, he had to follow consecutive sets by Rock and Chappelle.

Rather than feeling the pressure of inflated audience expectations, Morril says the grandeur of what had come before actually lightened the load.

“The crowd is in a good mood, because this is what they dreamed of. When you go to the Cellar, that’s what you hope happens. So I’m going up there with house money,” he says. “Anything I give them is a bonus.”

As most in this situation will do, Morril made light of the circumstance, giving him a laugh right out of the gate.

“You have to address the elephant in the room,” he says. “I said something along the lines of, ‘You just saw two of the most iconic comics of our time, and now, some dips*** you never heard of.’ That got a huge laugh.”

The presence of A-listers can even turn into career opportunities for newer comedians. Jim Tews was performing in a “Whiplash” show at the Upright Citizens Brigade in 2013 on a night when CK dropped in. The famous comic watched Tews’ set and wound up hiring him to perform on his wildly popular FX show, “Louie.”

“Luckily, I had a good set,” Tews says. “That was a weird added pressure, since I knew he was there. I was like, well, I better not suck. I came backstage after and he was very complimentary.” Tews got a Twitter message from CK a month later; CK asked to see more of his material and eventually hired him to perform on the show’s Emmy-winning episode “So Did the Fat Lady.”

But as great as these sets are for clubs, crowds and newer comics, their deepest value is felt by the superstars themselves. Several years into her career, Boosler was still living with Kaufman and still scrounging for spots, but she had more confidence in her abilities and her place in the stand-up community.

“One night, Andy came in and said, ‘I have to do an hour tonight,’” she recalls. “The club owner looked at me and said, ‘OK if your boyfriend takes your spot?’ I said, ‘No!’ Andy said, ‘Right answer. Now you’re a true comic. I’m so proud of you.’ And he kissed me, then said, ‘But I’m still taking your spot.’”

Larry Getlen has written for New York magazine, Time and Esquire, and is a regular contributor to the New York Post. He once saw Dave Chappelle surprise a half-empty bar in Manhattan with a half-hour set riffing on the DJ’s albums.

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