If there’s one thing that rivals former The Tonight Show host and career funny man Jay Leno’s delivery of a well-timed quip, it’s his insights into all things auto. A lifelong gearhead, Jay’s comedy chops slide to the back burner when it’s time to talk rummaging for old car parts, hitting heavy traffic in a restored 1909 Baker Electric Coupe and what makes a Porsche 911 great.
A big-time collector, he maintains nearly 200 cars (including classic models, muscle cars and modern marvels) and more than 150 motorcycles in his Burbank, California, garage. The iconic space, lined with illustration-style murals of vintage cars, serves as the backdrop for Jay’s CNBC-turned-YouTube series, Jay Leno’s Garage, where the automotive aficionado reviews anything that rolls, tackles car-related challenges and interviews his famous friends.
This month, both sides of Jay’s repertoire are on full display during the Naples Automotive Experience, running February 6 to 8. On Thursday, the comedian headlines an opening night performance at Estero’s Hertz Arena to benefit St. Matthew’s House, with proceeds supporting the nonprofit’s work to turn the tides on hunger, homelessness, addiction and poverty in Southwest Florida. The following afternoon, Jay hosts an exclusive tour of the car collection at Naples’ Ultimate Garages, an exotic and luxury car storage facility and event space. The weekend culminates with Cars on 5th on February 8. “It's one of the great car shows,” Jay says.
Jay leans into the nostalgia behind older models—the feeling of wrestling with manual steering holds a special place in his heart—but doesn’t shy away from progress. While many classic car collectors are sticklers for original parts, he appreciates that some aspects, like brake systems and seatbelts, are logical places to introduce modernity. “Mark Twain said, ‘I like progress. It's change I don’t like.’ That's the trouble with a lot of old car guys. I have some car magazines from the turn of the century. [In one], this guy was saying, ‘What's going to happen? Are they going to replace all the blacksmith shops with gas stations?’ Well, yes,” Jay says with a chuckle.
Among his myriad classic and historic models, the car enthusiast keeps an electric Tesla for daily use—it’s low-maintenance and offers bang for your buck, he says—and has a 2025 Ford Mustang GTD on the way. “I think we're living in the golden age for cars right now,” he says. Still, don’t be surprised if you catch Jay cruising Naples in a classic Cadillac during his stay along the Paradise Coast. The “big and slow” behemoth makes for a stylish tour of the slow-paced, flat landscape, he says.
If you see him, don’t be scared to pull him aside for a chat about horsepower. “This is what I do. I go to car shows and events,” he says. “When people stop me and say, ‘Hey, Jay, I got a 66 trans,’ I say, ‘Oh, great. We can talk about cars.’ I enjoy meeting the public because I'm exactly who they expect me to be. That makes it fun."