Here’s Waldo: A Day with an American Icon

Anthony DeThomas
Oct 19 · 4 min read

For my latest piece, I spent a day with the red-and-white-striped icon of “Where’s Waldo” fame, Waldo, for a Q&A about what it’s like to influence so many.

The text on my phone says, “hot dog stand. Times Square.” Another text comes, “this is Waldo, btw.” That must be from Waldo, I think to myself. My feet shuffle with excitement and I can barely contain my smile. Waldo has been my idol since I gained the cognitive ability to have an idol. He has millions of followers, gets to travel all around the world, and always attends the coolest events with so many people! Truly the American Dream.

Once amid the neon and flesh of Times Square, I realize Waldo didn’t say at which hot dog stand to meet him. I spend 20 minutes combing through the crowd. Finally, I see his red and white striped shirt and beanie peeping out from a group of Germans, who I can tell are German by their shirts, which say “We’re German.”

“Can you get a candid of me with that dog in the background?” he asks, handing me his phone and assuming a pose amid the bustle. “I’m getting to take Waldo’s picture!” I say out loud, to no one.

Fifteen minutes later, Waldo is happy with the angles I’ve managed to get of him in his fair-labor shirt and beanie, made by actual sheep (the sheep make the clothes AND are compensated fairly for their labor — what a progressive consumer Waldo is!)

Wandering into Williamsburg, we run into not one but two guys dressed just like Waldo at the same brunch spot. Once Waldo has satisfied their requests for pictures, he explains to me the burden and sacrifice of influencing so many people, “It’s, like, a civic duty I’m doing. I share my creativity and my unique look with the world. Yeah, it’s annoying when people appropriate it, like Warby Parker knocking off my incredibly round Waldo frames but nobody will ever be me.” I ask him what his inspiration is but he’s too engrossed in his phone to notice (people aren’t going to influence themselves!)

We’re navigating Central Park. Waldo has somehow managed a wardrobe change. I follow my court-jester-clad interviewee through a Renaissance Festival entrance. Waldo lets me take pictures of him amid the spectators of the jousting tournament, where he insists on capturing footage of himself next to an impaled jouster, who asks for an ambulance while clutching a hole in his abdomen. “Ew, people are so awkward,” Waldo says as he walks away.

I’m then deputized to capture Waldo amid the crowds of runners at the starting and finishing lines of a charity 10K in the middle of the city. He doesn’t run in the race and he didn’t donate. That “misses the point,” he explains to me as he repositions his now sweatband-covered arms to mimic a running motion. “See, nobody wants that canned b.s. influencer stuff. It’s so overdone. I enjoy being in the moment too much, and meeting people, having real conversations,” he says at me while checking the comments on his post of the now-deceased jouster.

We hop off our diesel powered scooters (thanks Uber!) and Waldo lets me snap some shots of him among the drum and hum of a large climate protest. I even get a funny shot of him tossing a plastic water bottle close to a trash can. I follow as Waldo films himself boarding a private jet to a concert two blocks away. (It’s hilarious when he uses a furry animal filter!)

I grab a few dozen more pictures of Waldo in the riffraff of what appears, in the pictures, to be an amazing time at the concert. As further evidence of the unreal time Waldo is having, I snag an incredibly poor quality video of the band, of which Waldo has just learned the name (what a life!)

Waldo and I stand in line at a new, tiny-pie shop. After I document his attendance of the shop’s crowded line, he says he’s tired and live streams himself moon-walking home (he’s so talented!)

I sit alone eating six tiny pies and just smile. What an unbelievable day with a national treasure, I think to myself, brimming with fulfillment. And even without a single real question answered, I will go on the record saying Waldo is truly an American icon.

. . .

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Anthony DeThomas

Written by

innovation consultant | breakfast sandwich authority | hand hygiene enthusiast

The Startup

Medium's largest active publication, followed by +539K people. Follow to join our community.

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