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I like to lie awake at 3 a.m. By like I mean “endure” and by lie, I mean “toss restlessly” and by 3 a.m., I mean 3 a.m. I usually combat this wakefulness by putting on Jake Gyllenhaal’s reading of F. Scott Fitzgerald’s The Great Gatsby on Audible, which I’ve listened to more or less every night since March, 2020. Fitzgerald’s genius sends me to slumber.

When that fails, I accept my lot and I ask myself a question. Why waste insomnia? Such was the case last Sunday, when in the darkness I wondered, “What is the ugliest car?” It seemed like a simple question. After all, it’s easy to start a list of objectively beautiful automobiles:

  • Steve McQueen’s 1967 Ferrari 275 GTB/4
  • Diana Dors’ 1949 Delahaye Roadster
  • Jim Rockford’s 1974 Pontiac Firebird Esprit
  • James Bond’s 1963 Aston Martin DB5
  • A 1928 Duesenberg Model J Convertible J-531
  • American Graffiti’s 1958 Chevrolet Impala
  • A 1971 Chevrolet Chevelle
  • John Wick’s 1969 Ford Mustang Boss 429
  • A 1926 Ford Model T

Does this mean the ugliest car ever built is simply the opposite of a 1928 Duesenberg Model J Convertible J-531?

Not quite. Beauty is in the eye of the beholder. Ugliness goes much deeper - especially when discussing cars - because beauty and ugliness are both so subjective. Italian author Umberto Eco wrote in On the Shoulders of Giants, “Once you set a criterion for beauty, a corresponding criterion for ugliness always seems to present itself pretty much automatically … Like beauty, therefore, ugliness is a relative concept.”

Top 10 ugliest cars ever built

So, the question was not:” What is the ugliest car?” but rather “What is the ugliest car I’ve ever ridden in, either as driver or passenger?” It’s not about a universal gross, it’s about a personal revulsion. “Ask a toad what beauty is,” wrote Voltaire. “He will reply that it is his toad wife, with her big round eyes protruding from her little head, her broad, flat throat, her brown back.”

I settled on the following criteria:

  • The car triggered a physical revulsion
  • If the vehicle were food, I would have spit it into a napkin
  • It was so ugly that even to this day remembering it makes me sick

I began by considering family cars. There was a Volkswagen Beetle in California, then a 1967 Volvo, followed by a 1979 Toyota Celica Supra and a 1982 Rabbit. These automobiles had charm. The Beetle was an icon, though I was in diapers in the backseat secured by a thin leather strap and didn’t know it at the time. The Volvo too was a classic. Black, manual transmission (of course), leather bucket seats, no radio, no air-conditioning. The white Celica Supra was terrific. It had a cassette player. The 1982 Rabbit is my favorite, the car of my dreams.

To the outside observer, several of my beauties would be beasts, but to my subjective eye they had charm.

Next, the cars I’ve owned:

  • “Champagne” 1991 Volkswagen Jetta – good car, got divorced and lost it. Bad memories but can’t blame the car.
  • White 1990 Dodge Spirit - Certainly ugly to look at. Put a lot of miles on it. Had heart.
  • Black 1999 Camry XLE V6 – Good-looking car. I gave it to a stranger named Kim Coffin who had been diagnosed with breast cancer and endured six rounds of chemo followed by bilateral mastectomies and lymph node dissections, 32 more rounds of radiation and a prophylactic hysterectomy. She needed the car to get to treatments.
  • Various black Dodge Grand Caravans – Ugly, yes, but good memories.
  • 2021 Mini Cooper Countryman – I love this car.

It occurred to me that the most “objectively” ugly car I’ve ever ridden in was my friend Peter Jupp’s 1979 AMC Pacer, which we nicknamed the “Moon Unit.” The AMC Pacer (the same kind you see in Wayne’s World) looked like a giant jellybean suffering from nuclear radiation poisoning. It was ghastly. The Moon Unit had a small hole in its flooring which we used as an ashtray. We would take it to parking lots and spin donuts. It was as ugly as a toad and I loved its bulging front headlights and its misshapen frame.

As an hour of sleeplessness passed, I was coming up with nothing. I’d found traces of beauty in most of the automobiles I’d ridden in, or at least nothing truly objectionable. Then I recalled the limo I took from Toronto’s Pearson airport back in 2014. I was coming off a delayed flight and my luggage was lost. I was burnt out, irritable and impatient. I’d had enough delays and frustration and decided I’d take a limo home. I stood in the line and waited my turn.

As I stepped forward and a black minivan (like the one I owned) pulled up. The attendant gestured to it. I could almost smell its “minivan interior.” Sweat, in the form of disbelief, tricked down my neck.

“What’s that?” I asked.

The driver was out now, getting ready to open the trunk. The attendant was confused.

“I’ll be goddamned if I’m getting in that car,” I said. “Get me a new one.”

Thus rejected, the minivan driver moved on and a sleek town car pulled up. I took that one. There was no way I was going to pay premium to take a minivan. Looking back on it, that town car was the ugliest automobile I’ve ever ridden in, not because of the way it looked but because of the ugliness I brought inside. I was the ugliest thing in it.

That was my three o’clock epiphany. Whether it’s relationships, sculptures or automobiles, it’s not what you see that determines beauty or ugliness, it’s what you bring that casts the world in shadow or in light.

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