Jon Stewart Seems Pretty Chill

Sock puppets, a tiny chair, and some big thoughts.

Jon Stewart on Franklin Street, Tribeca, c. 1993. Photos by Chris X Carroll

My friend Patty and I had stopped at  a pitiful yard sale while on a job down South. You know, the kind where the announcement sign is weathered and faded. Not like, “Hey, everybody go through their closets and clean out the junk for beer money!” No, more like, “Desperate, crushing poverty where people are trying to sell any piece of junk they can find to buy a bite to eat.” Patty and I felt so bad we picked out some stuff just to be able to toss these poor folks some ducats. We tossed everything in the garbage at the rental car return on our way out of town. Everything but the sock monkey. Not the good kind of sock monkey, made from LL Bean ragg socks. The red heel (or toe, is it?) ends up being lips and the pair of socks forms a reasonable simulacrum of a cartoon simian. The sock monkey we bought at that benighted yard sale was just a sock with some googly eyes taped on it. I suppose it was an homage to Kukla, Fran, and Ollie but it was really just super lame. So cheesy I almost couldn’t bear to bring it on set. Patty and I thought it was hilarious, and wore it on our hands to make dinner and walk the dog. Socky had become another member of our quirky little family. Unclear if anyone else would even deign to put their hand inside the filthy thing.

When Jon Stewart comes to your photo shoot, he understands the assignment. He didn’t just agree to work with my psychotic googly-eyed sock puppet, he worked it, hard. Indeed, it was his idea to have Socky smoke a butt. I mean, I allowed (Encouraged? Unclear) him to smoke so probably not much of a jump to the puppet. At that point in his career in the early 90s, (I photographed him twice, several months apart) he was a standup comic. Comedians are a weird breed. Photographing them can be so great when they engage their talents to collaborate and create art. Other times, they are so neurotic and paranoid that it’s all you can do to finish up the shoot and get out of there. 

The hell is this smoking sock business?

Stewart is definitely of the former ilk. We rented a classic retro microphone, planted him in front of a red velvet backdrop, and let him go. As always, he got it and immediately figured out what was best for the picture. Just as with the smoking Socky, Stewart affably listened to the brief, then got with the making of the pictures. He was kind of the opposite of a musical one-hit-wonder; those guys think they’re destined for greatness and really their career is over before it even started. Stewart, on the other hand, was humble, imaginative, and down for any and all wackiness. I think in Zen it’s called “Beginner’s Mind.” Terrific fun to be around, super professional, just fun to hang out with. 

Thus, when he returned to my studio several months later to shoot for a different publication, he was not too nonplussed when I explained that I thought it would be funny to shoot in this weird little child’s chair I’d found while walking Otis that morning. This was, of course, way prior to the bedbug scourge of the ‘aughts. Still, sketchy street furniture was really just an easy step from Socky’s unknown provenance the last time—and that turned out pretty good. 

Kids beware, smoking may make you successful beyond your wildest dreams.

That chair was weird. In typical NY style, I spied it on my early morning walk with Otis. I immediately picked it up and shlepped it home. It was the weirdest thing, fugly beyond all reason. Sturdily made, it encouraged sitters to stuff themselves and their adult hips into this tiny rectangular box. Simultaneously comforting, Temple Grandin’s hug machine for cows comes to mind, yet disconcerting. You know how that Wonder Woman pose, hands on hips, is supposed to lead to greater confidence, bigger paychecks and more fulfilling sex? Yeah, well, this chair was like the anti-confidence maker. Stewart was delighted to traipse downstairs and out into the middle of Franklin Street to plop down in this weird little chair that makes you look positively goofy. As always, he understood the assignment, matching the odd platform with a bemused “What, Me Worry?” expression to match his posture.

My wife, the former wardrobe stylist, tells me the only giveaway to the vintage of that thirty-year-old photo is the shoes. It’s true, the guy doesn’t look any older nowadays (well, the biblical beard aged him, but now that he’s clean-shaven again, my point stands), and that was decades ago. I suppose affability, hard work, and righteous humor keep you looking preternaturally young. Go figure.