Joel Karie was returning from a trip to Maryland on Thursday, having left that morning to make rehearsals at the Minskoff Theater, where he is a singer in The Lion King. He had just pulled over on 10th Avenue and 44th Street to hop out so his partner, Derek, could take the wheel. Just then, a red-and-black Mini Cooper pulled up behind them, and an older gentleman with a salt-and-pepper mustache got out.

“He wanted to know if I actually liked it,” Mr. Karie told The Observer. “People seem to have a very positive reaction, but then they want to know if we enjoy the car as much as they seem to.” It was the same reaction Mr. Karie has gotten not only driving around the five boroughs for the past two months, but also on the streets of West Baltimore and at a Delaware rest stop. “It’s kind of ridiculous” how much attention the car draws, Mr. Karie said.

He is the proud owner of a brand new Fiat 500, one of only a few hundred in the metro area. He opted for the 500 the sport model, because it came in the color he was looking for, Tropicalia Yellow. “It cost a few thousand dollars more, but that’s what I like about the Fiat,” Mr. Karie said. “I didn’t get a small car because I couldn’t afford a better car. Really, really both of us wanted to buy an American car. However, when you go under $20,000 in an American car, it feels like you get what you pay for. I don’t get that pop I get with the Fiat. You can buy the baseline 500 and it doesn’t feel like the baseline.”

Mr. Karie is one of a growing number of New Yorkers making this very calculation, buying what the auto industry refers to as A-type or “city cars,” but what The Observer prefers to think of as clown cars. The Smart Car has been tooling around our streets in almost laughably limited numbers since 2006, its two seats reminiscent of latter-day Phaeton buggy. The following year, another European import arrived, BMW’s re-engineered Mini, and it has colonized every corner from the broad avenues of midtown to the brownstone streets of Brooklyn.

Now, the Cinquecento, as it is fondly called, has been popping up all over the city, part nostalgic coincidence, part cutting-edge Euro-cool, all concerted marketing push.

“The whole thing started in New York,” said Ariel Gavilan, head of communications for Fiat North America. “When they started to research the car, one of the places they did their research was in New York, even before they ever knew it would be for sale here. New York is a cultural hub, a megacity. It is the epiphany—the pinnacle of a modern city. It is a global icon. Like the Fiat.”

Why the Fiat 500 Is Perfect for America: ‘It’s the Obama Car!’

The new 500 Cabrio convertible was first unveiled at the Javits Center in April, at the annual New York International Auto Show, and not at the typical conventions of Geneva or Detroit. The first North American media availability was here—O.K., so is every media availability—but so too was a public meet-and-greet in Times Square two weeks ago, a public art installation of full-size fiberglass 500’s and giant pots for pear trees (It’s green!), and, on Sept. 8, Fiat will debut its Gucci-branded 500 on the opening night of Fashion Week. A major media campaign is underway, reaching TV, radio, billboards and—this being an Italian car—the cinema.

Nationwide, Mini sold 28,273 cars between March and July of this year, compared to 7,982 Fiats. The companies do not break out sales figures by city, but it does bare mentioning that the Mini is available in far more. The Mini is also having its best year ever, up 37 percent since the period in 2010.

Still, in a city with “New” in its name, where having the latest designer bag or rarest cut of heritage beef is a critical status symbol, the Mini’s popularity may be stalling. “The Cooper’s been the ‘it’ car for too long,” Jalopnik editor Ray Wert wrote in an email. “It’s time to see a shift for folks who are fashion-conscious, and this car’s got all that and a bag of artisanal chips.” In his review of the car, Mr. Wert declared, “The Fiat 500C is neither fast nor sporty. But how can you not have a blast driving a convertible this cute?”

New York has never been much of a driving town. Even after Robert Moses plowed a few dozen freeways across the cityscape, car owners have never been a majority. Yet car ownership has risen slightly over the past decade, according to the U.S. Census, from 44.3 to 46 percent, after seeing virtually no growth the decade before that. As gentrification brings more suburbanites to the city, they are bringing their cars with them. And while New York has never been much for car culture, it loves all things continental. As the city trades in its gritty streets for cute and cuddly byways, there is ever more room for cars.

“It’s a great rendition of the Cinquecento of the past,” said automotive designer Jonathan Kim. “I don’t think it’s the same as the original, because that is a different animal. That was a go-cart on wheels. The new one is like an adult version of that. It’s smart and well-tailored.”

Mr. Kim actually drives a white Smart car, from which The Observer caught him unloading groceries on Wythe Street on Friday night. He is an inveterate gearhead who spent seven years designing cars for Ford, including the new Mustang—the interiors are all his—and a Bronco concept car that eventually became the new Land Rover LR3. After a stint in Europe, he returned to New York around the time the Smart Car was being launched Stateside and fell in love, especially for its park-anywhere capabilities. “Everyone is jealous,” he said. “Everyone.”

He does appreciate the appeal of the 500 for New Yorkers who might not be able to commit to the Smart Car. “The position in the Cinquecento is high, just like in the Smart, which is good, especially in urban situations. You can always see a little bit over the traffic, which is what we call in the industry the H-point,” Mr. Kim said. like the design-centricness of it, it’s quite nice. There’s a nice color palette and just an array of choices to fit your modern tastes. They’ve got a great marketing component, they’ve really targeted it to the modern, urban 20- and 30-something. And they avoided the pitfall of the Volkswagen Beetle. They made the Beetle a little too retro-cutesy, whereas the Cincquacento is the kind of the modern interpretation of the older version. So you don’t get the people who grew up with the Cincquacento; you get people who don’t even know what the Cincquacento is.”

There is also the advantage of the New York’s ethnic heritage. “The Mini is more sporty, it’s a bit bigger than the Cinquecento. When you drive a Mini, it’s good; when you drive a Cinquecento, it’s passion” said Claudio Coronas, proprietor of DOC Wine Bar and DOC Wine Shop on the north and south sides, respectively, of Williamsburg. “I’m Italian. It’s my first car, I learn to drive with a Cinquecento when I was 15 years old. For me, maybe it’s something that’s more than a car. It reminds me of when I was younger.” The native Italian bought his car through a limited-edition auction last year. It is number 487 out of 500, and it was delivered in May. He laments its inability to fit more than one stroller in back, as the two Minis he owned before could, but in addition to his BMW, he said it was the perfect city car, and one he drives far more often.

“Especially in Brooklyn, they don’t like the big S.U.V.,” Mr. Coronas said. “It’s all old Volvos and Suburus, the electric, hybrid. The first thing everybody asks is how many miles on a gallon. The first thing—‘Cool, cool. How many miles?’” The answer is 30 in the city, 38 on the highway. That is in five-speed manual. Opt for the more American automatic transmission and it’s 27 miles per gallon in the city, 30 on the highway.

“The Fiat 500 is absolutely poised to become the new ‘it’ car for BroBos,” Jalopnik’s Mr. Wert said. “It’s cheaper than the Mini, smaller than the Mini, and, while still looking retro, doesn’t look at all like the Cooper.”

Yet the bigger challenge may be converting those who are not automotive or Italian devotees—one Fiat is having no trouble with. “The aesthetic is very sensible,” Mr. Karie said. “I hate driving, I’m not a huge fan of it, so anything that enhances that experience is good. I feel very comfortable in this car. It’s like an Apple computer. Aesthetics and design can make something boring fun. It’s not just how it looks but how it works. It’s nice to know someone has put some real thought and care into the product, instead of just stamping it out on an assembly line. If I’m caught in traffic, I want to feel good being stuck.”

It is a small sample group, to be sure, but three of the four new Fiat owners The Observer spoke with happened to have owned a Mini previously, including Mr. Karie. “I can get more bang for my buck this way,” he said. There is roughly a $5,000 spread between the two. Beyond that, the 500 is smaller, albeit by five inches, and with a smidgen more head room but half an inch less leg room. There is better fuel economy. Most important, and almost unquantifiably, there is what the Italians call sprezzatura.

Even Fiat dealers have picked up some Mini converts. At the new Fiat studio at the corner of 11th and 51st—a block down from The Daily Show studios—George Gaeta has been closing deals since the dealership opened in April. “I used to work up the block,” he told The Observer Monday evening, referring to the BMW/Mini dealership at the corner of 56th Street, on the other end of Manhattan’s automotive row. He had just finished selling twin sisters from Michigan on the car. “It’s not that powerful, but it’s a lot of fun to drive, especially in the city,” said Lianne Rinaldi. “We remember it from going to Italy as kids,” added Carla Rinaldi.

As for concerns about “Fix It Again Tony,” the notorious reverse-acronym from Fiat’s first entry into the States, Carla noted, “That was before we were even born.” With the current offer to pay down parking to $99 a month, for some it is too good a deal to pass up. Caleb Denis, the dealership manager, said one man called the car free because he was paying $350 per month in car payments on top of $450 in parking. He drove home in a Fiat that day.

mchaban [at] observer.com | @MC_NYC

• 1
• 2
• 3
• All

Matt is The Observer's real estate editor. Follow Matt on Twitter or via RSS. mchaban@observer.com