Becoming Debbie

How doing drag connected me to my alter-ego

From the moment I saw her—driving a 500SL Mercedes at high speed, chasing after Uncle Fester—I knew Debbie Jellinsky would be a part of my cultural shortlist forever. With her all-white wardrobe and prickly pink vibe, the character touched something in me.

The film Addams Family Values came out in 1993 when I was just six years old, but it changed how I look at feminine power, humor, and vanity license plates. It also cemented my love of Mercedes-Benz models of the 1980s and 1990s, arguably the brand’s heyday.

I would go on to watch the film over and over—sometimes around Thanksgiving in honor of the summer camp scene where Wednesday Addams, played by Christina Ricci, playing Pocahontas, roasts the white pilgrims who have invaded her native lands—or whenever I need a funny, familiar, comfort-food movie from my childhood.

All of the characters and actors are iconic, but Joan Cusack as Debbie Jellinsky, the scheming, gold-digging black widow is by far the most fun.

I always said that when I got my classic Benz, I’d also get a vanity plate referencing the second Addams Family film, which puts Cusack in both a white Lincoln Town Car (with burgundy leather interior no less), known by its New York vanity plate as DEBBIE1, and the white 500SL, known as DEBBIE2.

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In early 2024, I bought a 1998 Mercedes E320 sedan, a car I have liked since its debut in the mid-90s when I was 11. That generation is called the W210 E-class, and was produced from late 1995 until 2002 with a mild facelift in 2000. I wrote a post at that time explaining my reasons for buying an old car if you’d like to read more about it.

Although it isn’t the SL roadster with a V-8 engine like in the movie, I felt one step closer to my Debbie dream. Shortly after taking possession of the gold over tan E320, I applied for the black and yellow California vanity plate “DEBBIE4”, as DEBBIE3 was already taken. She was thusly christened as Debbie to me, and Debbie to everyone I know.

Old cars have a way of seeming more human-like than brand new ones, in my experience. Their quirks mimic the variety and range of human traits.

As it turns out, the timing was rotten. Purchasing an aging German car always means spending money, and just a few months after taking ownership, I was laid off from my corporate job, which meant tightening my finances significantly. I ended up having to spend thousands to rebuild the transmission and replace elements of the suspension and engine. It wasn’t a frugal choice, and I’ve made similarly bone-headed money decisions in the past.

But I always felt excited to get her back from the shop, freshened and tightened, the same way I feel leaving a dental cleaning and how I imagine Debbie Jellinsky feels leaving the med spa. Not fun, but satisfying.

This year has been a dumpster fire in many ways, for me personally, for the world and for America. But Debbie has been a steady light in my days—stylish, classy, analog. Solid. And largely without protest since I moved back to Tampa.

I had to surrender my DEBBIE4 California plate but replaced it with one of Florida’s most aesthetic specialty license plates—the Rorschach-esque pastel “State of the Arts” plate that supports arts funding. This time I was able to snag DEB BI3. Florida only allows six characters or fewer on its plates.

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This Halloween, it struck me that I could attempt to become Debbie in the flesh and really play up the gag. I thought if ever there was a time to do this, it’s now.

And a gag it was. I regret now not having a full-on photoshoot with me in drag and the car.

My friend Mishou offered to help create the vision of Debbie in all white. Her iconic look is an off-the-shoulder dress with a bow motif around the bosom and a wide belt around the waist.

Mishou used bulk white fleece fabric from Walmart to sew a simple body-hugging number. She also teased my wig (I opted for brunette instead of blond to add my own twist), beat my face (did my makeup), and loaned me jewelry and accessories to round out the ensemble. She was my fairy Halloween godmother (pictured below)!

Debbie Jellinsky is a murderous psychopath, but I decided even a fake revolver might be too much, so I brought along a taser I bought while living in LA. It’s probably the only time I’ll ever use it.

Truthfully, the best part was assembling the look and getting ready. Actually being Debbie was bizarre.

Wearing a short dress and not tucking my junk anywhere—weird.

Not shaving any of my body hair, so having hairy legs, chest, and underarms while in full drag—odd.

Having people tell me I make a really pretty woman—awkward!

But it was a blast. I was a different person. Debbie felt like my natural alter-ego. My first real drag persona and pop culture muse. I stepped into my feminine power.

After all, Debbie Jellinsky doesn’t take any shit. She manipulates men, wraps them around her manicured nails, and then offs them when she’s had her fill—taking their money with her. She’s graceful, delicate. And not joking.

It was exhilarating and exhausting—and totally worth the $50 for fabric, shoes, and a belt.

Playing dress up also showed me what women deal with daily. The pressure to look pretty, to smile, to wear uncomfortable footwear, to cover themselves in product, and to appear effortless while making the most effort. And then be subjected to the looks and stares. It’s ridiculous and maddening and impressive.

Debbie isn’t just a silly character from an old film. She’s a force. It’s been a treat to channel her energy and claim her likeness for my car and my costume.

I imagine we haven’t seen the last of her, via me. Someday I’ll have a fleet of Debbie-dubbed Mercedes and a go-to drag look I can perfect. Stay tuned!