News & Politics

What Was It Like Sharing a Beach House With Jon Stewart?

Amazingly, he wasn't always the funniest guy.

The author (front row, in red T-shirt) was one of Jon Stewart's earliest fans—he's at the far right—thanks to fun weekends at the Delaware shore. Photo courtesy of Sherri Dalphonse.

While Jon Stewart’s final episode of The Daily Show last night has caused loyal viewers to reminisce about his 16 years at the satirical news show, I’ve been awash in memories of a different sort. Sure, I loved “Indecision 2000” and his brilliant jabs at “fair and balanced” Fox News as much as the next fan. But sometimes when I watched his show, and Jon would laugh that great cackle of his, it would take me back to the late 1980s and early 1990s, when I had the pleasure of occasionally sharing a beach-house weekend with the man we then knew as Jon Leibowitz.

The amazing thing is: Jon wasn’t always the funniest guy in the beach house. Anthony Weiner often made me laugh just as hard.

How did I get into a beach house with a soon-to-be TV star and a future congressman? My housemate at the time was dating Weiner’s housemate. Anthony and the housemate had befriended some guys who all went to the College of William & Mary, Jon’s alma mater.

Jon Stewart, Bethany Beach, August 1993. Photo courtesy of Sherri Dalphonse.

For several years, I went in on a share of whatever summer house they rented in Dewey and later Bethany Beach. When I met Jon, he lived in New York City—he was trying to make a go of standup comedy. That included gigs on most weekends, so he only came to the Delaware shore now and then. But even today I have memories of the times he visited.

We weren’t a particularly wild bunch. Sure, some of us probably drank too much, but we never trashed the houses (although I do recall occasional sand-clogged showers). Even now, I have more recollections of dancing to the English Beat and REM, of afternoons of beach volleyball, and of long Scrabble games than of playing quarters (although we did that too). Every summer now, when I think about those carefree weekends, it brings a smile.

We were an ambitious lot, and some were already fairly accomplished for their ages. That’s Washington for you—even in your twenties, you could see who might be a future leader, and who was whip-smart. But did we envision Jon becoming such a mega-star? I certainly didn’t.

In the early 1990s, a few years after we stopped doing summer rentals—people were moving away, getting married, having children—some of us gathered for a weeklong reunion in Bethany. Jon came, armed with a VHS tape of a new comedy segment he was working on, I believe for MTV. It was an exciting time for him—shortly after that, he’d be a finalist to take over David Letterman’s position (a job he lost to Conan O’Brien). Even then, maybe because it’s hard to imagine someone you know as a celebrity, I never predicted the heights to which he’d rise.

We were so young then, in our twenties, with so much of our lives ahead. This was before spouses and kids and mortgages, before deaths that came too soon, and before international fame and Twitter missteps. Not to say those days were all idyllic—your twenties come with their own set of challenges, usually involving money or romance. But looking back now, my biggest concern was often not big at all: getting to the beach house early enough on a Friday night—many of us drove there after happy hour at the Fox and Hounds in Dupont Circle—to get a bed for the weekend. (Although, I do recall some men gallantly sacking out on the floor to give a woman a bed.)

I once asked Jon why he had changed his name—he was born Jon Stuart Leibowitz. He said it was after he had auditioned for someone who cracked, “Great, another Jewish comedian.” I don’t know if that’s true; maybe it was a joke. The beach-house crew included some very sharp, quick wits—of which I admit I was not one. Even then, it was fun for me to sit back and be part of the audience. And laugh. A lot.

Editor in chief

Sherri Dalphonse joined Washingtonian in 1986 as an editorial intern, and worked her way to the top of the masthead when she was named editor-in-chief in 2022. She oversees the magazine’s editorial staff, and guides the magazine’s stories and direction. She lives in DC.