Photography by Matt Seidel
He remembers the lights. The first time Yale Hollander stepped onstage at Helium Comedy Club, they were so bright, he couldn’t see beyond the first row. Peering into the darkness, he quickly realized that reading the audience meant listening for laughs, jeers, silence. “I was just expecting crickets,” he admits.
On that summer night in 2016, some in the audience might have had their doubts, seeing a middle-aged lawyer in tortoise shell glasses and hot-pink chinos at an open mic night. “Sometimes I see guys who look like they’re doing a bucket list, almost: ‘My name is Steve, and I live in Ladue,’” says Tina Dybal, co-host of the Slop City podcast. That was her initial impression of Hollander. “He’s got his nice little smart glasses on. I thought, ‘That’ll be it.’”
Comedian Angela Smith remembers the first time she saw Hollander: Whose kid is his? she thought, sure he was there as a chauffeur. “He’s so official. He’s just very buttoned up. I just didn’t think he was there to do comedy that night—and then he got onstage.”
“So many people come and go in comedy,” says comedian Rafe Williams. “It’s almost like a war movie. You don’t learn someone’s name until you’ve seen him five times, because you think you’ll never see him again.”
Before making the leap, Hollander had written 30-plus pages of material, then edited it down to four minutes. He’d told his wife it was just something he wanted to try—nothing would come of it, he was sure.
Then he picked up the mic.
“It was just one of those things,” he says. “You either run screaming or you end up getting sucked into it. For me, it was the latter.”
When he came home after that first set, he’d already signed up for the next week. Five weeks later, he booked his first paid gig.
But it didn’t stop there.
“He just kept coming around,” recalls Dybal. “This is how good Yale is and how big of a part of the scene he is—I don’t even remember him becoming a part of it. One day we met Yale, and the next day he was running five shows that were very well attended.”
Since 2016, Hollander’s both performed and hosted comedy shows at a range of unexpected venues across the region. He’s on a mission to take indie comedy where it’s never been, to give more people access to standup. He’s also aiming to provide more opportunities for St. Louis standups to practice their art. It’s said that it takes 10,000 hours to master a craft. For standup comics in St. Louis, there are only so many opportunities to log those hours. Typically they’re accrued a few minutes at a time, at open mic nights at comedy clubs (Helium, Funny Bone, The Improv Shop, The Laugh Lounge) and bars (The Crow’s Nest, The Crack Fox). Aspiring comedians might prepare a five-minute set or wing it, then return the next week to polish the material, building a solid enough set over time to perform at a club or independent show. Hollander took it further. In addition to those open mics, he began hosting events in diners, outlet malls, cigar bars, coffeehouses…
Every standup hopes to make it big. Fewer want to organize the shows. Fewer still want to produce those shows beyond the typical venues. Exactly one wanted to put on a show on the Loop Trolley. For every five-minute set you do, produce a show that gives 15 other comics the same opportunity, your five multiplied by 15. That’s the Yale Hollander effect.
Early Material
Comedy always appealed to Hollander.
When he was a kid, growing up in Jefferson City, he’d stay up on summer nights to watch Johnny Carson and the rotating cast of standups: George Carlin, David Brenner, Alan King, Robert Klein, a young up-and-comer named Jerry Seinfeld.
When Hollander was in grade school, his dad bought him his first comedy album, Steve Martin’s A Wild and Crazy Guy, released in 1978. His father knew that Hollander liked the comic for his safe–for–Saturday Night Live song “King Tut.” What he didn’t know: Martin worked blue in his club act, which was on the album. “It’s difficult to go into in mixed company, but what the heck,” Hollander jokes before recounting the setup and punchline. “We’ve kind of gotten desensitized to it these days,” he says, “but for a 10-year-old in the 1970s, that was serious.”
In the fifth grade, Hollander tried out for the school talent show, paying homage to SNL’s “Weekend Update” sketches by creating his own satirical news program. “All of the teachers were cracking up,” he says. “None of the kids were cracking up, because it was just way over their heads.” It was his first lesson in reading an audience, he recalls, but “that’s when I kind of knew that I had something, if I could, as a kid, make adults laugh at something that didn’t involve a bodily function.”
Years later, while working as an attorney, Hollander fine-tuned his ability to read people. During the first decade of his legal career, he worked in debt collection, traveling all over Missouri, sometimes working with hostile audiences. “I spent a lot of time in the car on a lot of very, very boring rural highways,” he says. “It gives you a lot of time to think about things. I’d be listening to the radio, riffing on current events and trying to find sarcastic angles. But back then, I didn’t have the time to go out, turn it into anything.”
Eventually he found an outlet through writing, penning a column for the now-defunct St. Louis Globe-Democrat: “My editor finally said, ‘Your business columns are really funny. You should just write a humor column instead.’” Then he wrote for the St. Louis Jewish Light and the razor company Harry’s Five O’Clock magazine. Hollander mused on life as an ambitious lawyer, rising at 3:45 a.m. to put in a few hours of work before eating breakfast at the since-closed Layton’s. “Every now and then I drive past it and can see inside its vast plate-glass windows where the counter, the stools, the tables, chairs, and booths all remain in place—a monument to the mornings when I learned that the right breakfast can provide sustenance in both the physical and spiritual contexts,” he wrote.
His column on colonoscopies offered even more depth. “When you awaken, you will be greeted by a doctor eager to show you some pictures that he or she has just taken,” Hollander wrote in an essay titled “Here’s Lookin’ in You, Kid,” which provided both serious reflection on losing his mother to colon cancer and comedic relief about the actual procedure. “At first glance, these pictures may look like the inside of an abandoned mineshaft but, no. You, in fact, are the star of these pictures, only instead of your smiling face, what you are looking at is the inside of your colon.”
He also gained a social media following, forming a friendship with Ted Allen, who’d just completed his run on Queer Eye for the Straight Guy and was hosting the Food Network’s Chopped. “He told me that I should try getting into standup, because he really liked my stuff on Facebook and Twitter,” Hollander says.
Around the same time, Hollander started incorporating humorous asides in his work training other attorneys to make the sessions more engaging. A couple of people suggested that he try an open mic.
“When more than one person suggests something to you, unless it’s eating healthier, I’m probably gonna try it,” he jokes.
Photography by Matt Seidel
Dad Jokes
After that first open mic at Helium, Hollander thought, “There’s something here, and this isn’t very terrifying. I’m actually pretty comfortable up here. It was kind of relaxing.”
Several months later, he tried a different approach: opening with a greeting that lasted nearly two minutes—and that was the whole bit.
“Give it up for all the comics you’ve seen tonight,” he said, taking the stage. “Give it up for all the comics you’re gonna see tonight. Let’s give it up for your servers. They’re working hard for you tonight, yeah? All right. Let’s give it up for Terry the bartender, mixing up those drinks for you. We’ve got Helium corporate in the house. Let’s give it up for them. Let’s give it up for the people in the bathrooms right now, because there’s a PA system in the bathroom. Let’s give it up for the guy in the third stall…”
Hollander’s style has been described as storytelling, as that of a fiftysomething noticing the world around him and pointing out how ridiculous it is but still accepting of it—and self-deprecating. He jokes about his wardrobe, weight, age, his children. On Twitter, Hollander describes himself as a comedian, media gadfly, and “certified 93% funny.” While encouraging followers to support #STLComedy, his presence is a mix of bits (“Hear me out on this—a unicycle, but with TWO wheels”), observations from life as a dad (“If you ever want to REALLY try your patience, spend 10 minutes explaining what a bidet is to a 14 year old.”), and live-tweeting Donnybrook.
At Yale and Shari Hollander’s ranch home, in Ballwin, the lawyer/comic has just finished a task uniquely suited to his background: mediating an argument between two parties, his teenage daughters, and defusing a tense situation with humor.
Has he always been funny? Shari remembers Yale carrying Brett Hull and Wayne Gretzky hockey cards in his pocket during their wedding ceremony, 23 years ago, and, right before breaking the glass, yelling, “Let’s go, Blues!” (“It was during the playoffs,” Yale reasons.)
She loves that he makes the kids laugh. Both Mia, 18, and Faith, 15, attended Yale’s trolley shows. Mia’s let it slip that she and her friends watched some of her dad’s sets on YouTube. Mia and Shari are traveling to Tampa this spring, staying on the TECO Line. “Maybe Dad can do a show there,” their daughter joked.
“Which is really funny,” Yale starts, “because there is a comedian in Tampa who made a short film about him and a friend who took a microphone and a PA system onto the inter-terminal tram at Tampa airport. They told jokes on there, just as a complete pop-up type thing.”
You can see the wheels turning.
The Show Rolls On
Here are the “Five Stages of Reacting to the News That Yale Hollander Is Going to Stage a Standup Comedy Show on the Loop Trolley,” as told by fellow comic Chris Cyr:
1. Roll your eyes.
2. Kick yourself for not thinking of the idea first.
3. Feel immense disappointment that you can’t perform in the show, because you’re already booked.
4. Feel a little jealous at how much publicity Hollander and his show are getting in the leadup to the event.
5. Realize how out-of-the-box your pal’s idea is and admit you’re proud of him.
Last August, Hollander announced that he was partnering with the Loop Trolley Company on a new venture called Laugh Tracks. The event was billed as a monthly standup night on the streetcar, which before closing, at the end of December, ran on a 2-mile stretch along Delmar Boulevard.
“The trolley seats 45,” Hollander says. “My hope was that we had no open seats. My hope was to get 45 people. For an independent comedy show, that’s pretty decent.” The first show had 65 people, standing room only.
Outside The Pageant, the line waiting to board the trolley stretched down the block. KMOV showed up. Once aboard, a gaggle of comics performed their sets on the PA system as the trolley rolled along. Twice during the show, when the trolley reached the end of the line, everyone had to do an about-face, and the comics and driver moved to the other end of the car.
“What I envisioned was this big sloppy show where everybody would have fun, including the comics and the driver,” he says. “It was semi-chaotic but exactly what I wanted.”
Several months later, performing at the Happiest Hour Comedy Series at Sophie’s Artist Lounge & Cocktail Club, Hollander wears a T-shirt emblazoned with the outline of the streetcar and the words “Rolling Comedy Club,” St. Louis County Executive Sam Page’s name for the trolley. It’s just been announced that the trolley only has enough cash to operate until December 29, 2019—after that, it’s looking for new management. So Hollander works the news into his act: “Who else do you know shuts down a line of mass transportation by having comedians come on?”
Although Laugh Tracks is at least temporarily suspended, Hollander is working on other venues, including the Gaslight Theater, in the old Gaslight Square district. “And I’m never going to give up the quest to bring more comedy to West County,” he says. “That’s been a bit of a challenge and will probably continue to be a bit of a challenge, but I’ll land venues where I can for as long as I can.”
Smith is also performing at Sophie’s that night. She puts it simply: “As long as the owners want us to keep doing this and comedians are getting to work out their stuff, we’ll keep doing it. Then we’ll pack up and take the circus somewhere else.”
Photography by Matt Seidel
Funny Business
When Hollander started pursuing comedy, many indie shows had a short shelf life, and the idea of hosting one was appealing because, he says, “My goals are very modest.” He was looking to build not an hour but rather a tight 15- or 20-minute set. “Especially as other shows were kind of dying out, I wanted to start my own.” He pitched Zach Gzehoviak, co-founder of the Flyover Comedy Festival, the idea of a monthly show that would be half open mic, half longer-form showcase at Brennan’s. He took over another at Foam that later moved to The Monocle.
“Without people like Yale, we would still only have a couple of rooms,” Smith says. “We’d have our comedy clubs, and we’d have a handful of open mics. But with Yale doing these things, I think, it inspires other comedians to run their own mics and their own showcases.”
That Hollander is running shows in non-comedy venues and areas without an abundance of standup is even more remarkable. In a non-comedy venue, Williams notes, comics perform for audiences who might not be used to comedy shows. And it’s not like a concert, where the audience can drift in and out; if you miss the setup, a punchline’s not going to land. “You’re really going to find out if the material works or not,” Williams says, “because you have so many other obstacles and challenges. I mean, you’re on the Loop Trolley on a CB radio.”
Hollander’s greatest contribution to the scene is creating stages, says Williams: “I know a lot of really good comics who’ve never run their own show, never provided one second of stage time for anybody but themselves. If we all thought that way, where would we get better? How would we improve the scene?”
Cyr chalks it up to Hollander’s maturity. When you’re older, there’s a deeper well to draw from: “You start thinking about how to create stages as well as use them. You have to have something in the pot to take something away.”
It’s that last point that resonates with Hollander. He views comedy as a passion, a “self-financing hobby” (though he’s quick to backpedal on the use of the word “hobby,” like people who play golf a couple of times a week, when there are people pursuing the sport as a career). “I kind of have guilt,” he says, then pauses as if to consider whether that’s true. “Well, yeah, I mean, I’m Jewish, I have guilt. But I feel like every time I take up a spot at a club, I’m taking an opportunity away from somebody who’s trying to make a living doing that. Kind of like replacing a divot on a golf course, I always want to make sure that I’m creating as much, if not more, time for others as I’m taking up somewhere else. It’s not just for the comics—it’s the people who run the venues, it’s the people who come out and support the shows around town. I have such a great affinity for them that I love being able to do positive things to give them another opportunity.”
Off the Rails
It’s 7 p.m. on a Friday at Back Door Comedy & Events, and Hollander is hosting a show with headliner Kenny DeForest, a Springfield, Missouri, native who’s performed on Late Night With Seth Meyers.
The first sign that the evening might get a little lawless is the man in the audience wearing a “Keep America Great” trucker hat and Canadian tuxedo. The second sign: This gentleman is holding a small white dog. The third sign is a literal sign, bearing a message of misguided self-confidence, under which the man sits: “‘Trust me, you can dance.’ —Vodka.”
It takes DeForest exactly six minutes to comment on the canine presence.
“It’s my service dog,” the man replies, trying to joke. “It gets me serviced.”
DeForest replies, in a singsong voice: “This is a verrryyyy straaaange staaaaart.” He playfully prods further: “I can’t believe you’re a free man. Is there a prison around here?”
The man, game, replies, “I’m on work release tonight!”
“Oh, good,” DeForest fires back. “That’s the kind of guy who offers you moonshine made in a bathtub.”
The crowd, small, around 10 people, is in stitches. Hollander is bent over the DJ booth in the back of the venue, laughing into the crook of his elbow. Then DeForest makes a critical error: He mentions high school. Not even high school, really, but high schoolers. Doesn’t matter. The audience picks up on it, and two women strike up a side conversation about Timberland High School.
“Welcome to my meet-and-greet,” jokes DeForest. He can hear everything the audience is saying. “We call it a comedy show, but what it really is, is a PTA meeting for Timberland High School. This is wild.”
“Michael”—DeForest calls out the club’s owner, Michael Tobin, seated near the far end of the room—“I’m having a blast.” Can Tobin get things back on track?
Tobin can’t help himself. He lobs a grenade: “You know what, Kenny? I did all the infrastructure at Timberland High School. Fiber optics...”
“Oh, shit!” DeForest exclaims. Now he’s laughing at the audience.
“I’ve never seen people get so excited about a school district,” DeForest says. “All right, well, I’m just gonna let you guys descend into madness.”
Hollander gets back onstage to close out the show: “You guys, one more time for Kenny DeForest. One of these days, he’s going to have his own hour-long Netflix special, and dammit, we’re going to be the first 20 minutes of it.”
Last Laughs
During a recent open mic night at Helium, Hollander needs little introduction. “I don’t know if we should thank him or hate him,” the host quips, “because he intended to keep that damn Loop Trolley going.”
Stepping onstage, Hollander retorts, “Murderer of mass transportation—I’ll take it.”
He continues: “It’s good to be back at Helium. It’s been a while. This is the most unique comedy club in the United States. How many comedy clubs can you go to that have a f—ing two-story shopping mall in their attic?”
The set is a mix of new and reworked jokes, plus some tried-and-true ones. He claims that his comedy career is actually just a way to escape watching Lifetime movies and Dr. Phil with his wife at night, “or, as I like to call him, Mr. Phil,” he says. “He’s got a Ph.D. in clinical psychology, OK? OK, technically, yeah, you can call him a doctor, but come on, his doctoral thesis—I kid you not—his doctoral thesis was Psychological Interventions of Rheumatoid Arthritis. OK, so if you’re going on Dr. Phil, the only family problem you better have is that Grandma screams every time she tries to pick up a skillet. And yeah, I wrote that joke just so that I could use the word skillet. I have a J.D., I have a doctorate of jurisprudence. I’m a lawyer, OK? I don’t go around calling myself a doctor, OK? I mean, yes, I can fix your traffic ticket. I cannot fix your f—ed-up family.”
Four more minutes in the books.
“You guys have been a great audience. Thank you so much. My name is Mrs. Maisel.”
