Gerald Isaac "Jerry" Stiller (1927-2020)

post number twenty six

It’s an odd question, but have you ever thought about the moment you learned that you love to laugh? As in, when it became clear that your life going forward would involve seeking out people and experiences that could potentially cause that feeling?

My gateway into knowing I needed laughter as a frequent visitor came from an unlikely place (for a 7-8 year old black boy from Atlanta): The Dean Martin Celebrity Roast infomercials.

Roast informercials were my first binge watch. They’d be on for hours at a time on Sundays on like, channel 31. And I’d sit there, laughing at everything — both the jokes I didn’t understand and the people I didn’t know. Life became a journey to both understand these jokes and learn about these celebrities (and the connections they all had), while eventually figuring out if making people laugh would be part of my story.

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This love of roasts expanded into the New York Friars Club roasts, which they began televising on Comedy Central in 1998. The second televised honoree, in 1999: Jerry Stiller, who passed away today at 92.

The perfect honoree of a roast is someone who could properly roast his or herself. You know, real Oh, that’s your embarrassing story about me? You don’t even know the half, let me tell you about the time I did that, but this time in Bend, Oregon at 4:45am-type of energy. When that’s the case, the crass and crude jokes are welcomed, because you know they come from a place love, all in the name of the celebration.

That’s Jerry Stiller, sitting in his throne, for the duration of his roast.

The video is a true Y2K-eve time capsule. In the first two minutes, there’s Jeff Ross interviewing Max Weinberg, which gets interrupted by Dr. Ruth (who Weinberg calls his favorite dance partner) and Janeane Garofolo interviewing Stiller’s son, Ben. Soon after, roastmaster Jason Alexander (who plays Stiller’s son on Seinfeld) walks on the stage and immediately starts singing.


His song is about about how he got a voicemail about hosting a roast for “Jerry” and then the message abruptly cut off. People, in his song, he assumed the roast could be for:

Jerry Springer. Jerry Falwell. Gerald Ford. Jerry Garcia. Jerry Zucker. Jerry Lewis. Jerry Lee Lewis. Jerry Mathers. Tom and Jerry. Jerry McGuire. Jerry Brown. Jerry Van Dyke. Jerry Hall. Jerry Seinfeld.

This is how George Costanza began. Below, how he wrapped it up.

“Jerry, I love you and I adore you. I am your greatest fan. I am privileged to have shared a stage with you. I think of you the way I think of my own real father. As an old and seemingly endless drain on my patience and my pocketbook.”

Like every roast from an era ago, 20 percent of the jokes are completely irresponsible. But unlike many roasts (especially in the roast revival of the past 15 years), the person of the hour remains the most important figure. Even when Susie Essman is making fun of Chris Noth, it still comes back to Jerry.

The increased presence of death in our lives since COVID can make us numb. Chances are, when you find out about one person’s passing, you haven’t even spent proper time thinking about the last person. It’s hard. And I don’t know how to make it easier. It’s just where we are right now.

When it’s today, the fear of tomorrow’s news can show up early and announced. On this Monday afternoon, however, I feel grateful that that moment hasn’t arrived just yet. To honor that fleeting reality, it feels nice to honor Jerry — a man who made us laugh for so long.

Before the roast began, many of the guests were asked about one word they’d use to describe Jerry Stiller. At the end, Jeff Ross asked Jerry for an answer.

It wasn’t profound. It wasn’t a joke. And he didn’t even properly answer the question. But it was still beautiful.

“I’m still trying to do it right.”