No joke: This lawyer moonlights in comedy spotlight

Local attorney and stand-up comedian Yale Hollander performs at an open-mic night at Fitz’s in University City. Photo: Bill Motchan

By Bill Motchan, Special to the Jewish Light

In the 150-year history of Congregation Shaare Emeth, Yale Hollander holds an unusual distinction. A few years ago when he was on the board of trustees, it was his turn to serve as Shabbat greeter.

“I always took the opportunity to strategically throw a little bit of humor in to get everybody into that relaxed Shabbat mood,” Hollander said. “That week, Rabbi (emeritus Jeffrey) Stiffman was hosting a screening of ‘Blazing Saddles,’ and I announced, ‘This event is BYOB — bring your own beans.’ ”

The reference to the movie’s signature campfire scene was probably the only time anyone had ever told a flatulence joke on the bimah. Hollander’s offhand remark even prompted Rabbi James Bennett to burst into laughter on a solemn occasion.

Hollander, 49, knows how to get people to laugh. He’s a lawyer, but for the past year, he’s been moonlighting as a stand-up comedian.


In mid-June, he took the stage at Fitz’s in the University  City Loop for an after-hours open mic night. The small audience consisted primarily of a dozen other local aspiring comics. Most of them were half Hollander’s age. He gamely attempted a joke that might fall flat with millennials. 

Here’s the set-up: Hollander describes his experience working intermission at a West County classic rock gig with a baby-boomer audience.

“I said, ‘Hey does anybody here like Bob Seger?’ A huge roar went up. Somebody threw a whiskey bottle in the air. Somebody pulled out a gun and shot the whiskey bottle! It was pandemonium. I said, ‘If you like Bob Seger, I have a joke about him!’

“The room fell silent. But I was invested. So I told the joke. ‘You know it’s a pain when you play chess with Bob Seger because every time he picks up the little horse, he says, ‘Ain’t it funny how the knight moves?’

“This joke got about the same amount of silence that you’re giving me right now. Because as unfamiliar as you are with Bob Seger, this crowd was unfamiliar with chess!”

The gag drew a few random chuckles. A few nights later, Hollander did the bit again, for a larger but relatively young audience at the Improv Shop in the Central West End. Hollander coaxed some laughs out of the 20-something crowd. He told me later that the age of the audience has a definite effect on whether a joke resonates.

“I don’t expect to have people rolling in the aisles for all of my set,” he said, admitting that comedy can be hit-and-miss. “I recently did two open mics in a row that were dreadful. If I had bombed any worse than that, Henry Kissinger would have sent me to Cambodia.”

Fortunately, Hollander usually draws laughs easily from friendly St. Louis crowds. It helps that Midwesterners are polite. Another plus: St. Louis has a burgeoning stand-up comedy scene that is very welcoming to newcomers.

“There is an unbelievable network,” Hollander said. “The people have been great. Within five weeks of engaging in this little endeavor, I already had an invitation to perform at a showcase at the Helium club. I would never in a thousand years have expected to be five weeks into something and have somebody say, ‘We’d like to pay you to do stand-up.’ ”

Even other local comics give Hollander high marks. Chris Cyr says Hollander’s big advantage as a newcomer is his comfort speaking in front of people.

“He has a great casual manner on stage,” Cyr said. “When you’re comfortable on stage, the audience feels it, and they’re more receptive to you. I think that’s a big help for Yale.

“He also writes a lot, which I personally respect. A lot of people don’t realize how much writing goes into crafting what might end up being just a minute-long joke. Yale takes that part very seriously, and that comes across in his performance. It’s been fun watching him find his voice and figure out the material he enjoys performing most. He has a lot of great experiences and insights that trans late well to stand-up.” 

Hollander is an easygoing guy with a ready smile and a wry outlook on life. He immediately puts people at ease, which has been a useful, disarming tool at his day job. Hollander, a former litigator, trains new lawyers for Cordell & Cordell. Often, he’ll toss in some humor to liven up a dry presentation.

He grew up in Jefferson City, where his late mother always left him and others laughing.

“She was often compared to Totie Fields,” he said, referencing the comic who was a fixture on the “Ed Sullivan Show” before her death at age 48. “She was one of those boisterous people, with a sing-song delivery, just generally silly. She had that reputation in high school, starting at Soldan and finishing in U. City.”

Hollander graduated with a law degree from Oklahoma City University and moved to St. Louis to began his career. He’s always loved comedy, but work and raising a family were his main priorities. He and his wife, Shari, have been married for 21 years; they have two daughters, who are now 12 and 15.

“I’m of no use to them whatsoever when it comes to doing their homework,” he said. “When they were off at camp last summer, I thought, well I have some free time, and I went to an interactive comedy show at Helium called Comedy Smackdown. 

“I started getting laughs! And one of the hosts came up to me and had some complimentary things to say about my wisecracks, so I went the following week to an open mic night at Helium and the rest is history. I was bitten by the bug.”

Hollander often tries out new material at open mics. He also is an in-demand host at comedy showcases. You can get a taste of Hollander’s humor and puns from his Twitter feed @YaleHollander. A sample: “I just heard a story about a guy who hit a 10-point buck with his car. It was an end-deer-ing story.”

Viewers of the local news commentary show “Donnybrook” on KETC-TV (Channel 9) may also be familiar with Hollander’s barbed tweets. The show’s panelists consider Hollander almost part of their family. Regular panelist and Post-Dispatch columnist Bill McClellan said Hollander is a welcome off-kilter correspondent.

“One of the neat things about ‘Donnybrook’ is the interaction with viewers,” McClellan said. “Some of the regular callers have become part of the show. Yale is the first of the tweeters to accomplish that. He’s good with words.”

Being funny comes naturally to Hollander, but he says writing jokes is tough.

“It comes out of nowhere, and the harder you look the more elusive it becomes,” he said. “You set aside time and say,  ‘I’m going to go down in the basement and write jokes,’ and then nothing happens. Then I’ll be in the middle of rinsing shampoo out of my hair and something will come to me and I have no notepad or pen to write it down, so I’ll write it with my fingers on the mirror.”

Hollander loves the stage and making people laugh. He’s worked clubs, bars and any other venue where he can ply his newfound love for comedy. A gag he’s used to good effect is actually about working the clubs. It goes:

“I’m glad I get to work a comedy club. I used to work nursing homes, and half the crowd thought I was their doctor and the other half thought I was their grandson. When I worked the Jewish nursing homes, they thought I was their grandson the doctor.”

Hollander will be one of the contestants — a compuntitor — in the pun competition Punderdome on July 29 at Blueberry Hill.