How Does Jay Leno Decide Which Cars to Buy for His Obsession?

Jay Leno poses with a red Ford from his car collection
Jay Leno | Nicole Weingart/CNBC/NBCU Photo Bank via Getty Images

Jay Leno is into cars. It’s a pretty well-known fact about the late night TV star. The average viewer may not know where Leno got his start, where he’s from, or much else about him, but everyone knows he loves cars. 

Maybe love isn’t a strong enough word. He’s obsessed. He has over 200 vehicles in his collection. It’s not just cars. There are motorcycles in his collection, too.

He doesn’t buy just anything. He has very specific rules for which vehicles he buys and which he doesn’t. He’s had a long time to develop these rules, considering he’s been collecting cars since he was a teenager. He’s been into cars since he was very young. 

Why Jay Leno started collecting cars

Jay Leno has been collecting since long before he became famous. He started his classic car collection when he was a teenager. Not many 16 year olds can say they have a classic car collection, but Leno could. 

He was born and raised in Andover, Massachusetts. The small rural town was the perfect place for a young gear head to grow up. He would drive old cars around his backyard, or fix up broken down tractors. He seemed to have a knack for it. 

He then bought his first car at 14, before he even had his driver’s license. He started collecting soon after that. He truly hoards cars. He’s never sold one, although he has donated a few to charity. Individual cars in his collection are worth millions, but he doesn’t know the value of all of his pieces. He’s not even sure how much the whole collection is worth.

Jay Leno’s three rules for buying a car

Over the years, he’s developed three rules for deciding which cars he adds to his collection. He’s said his rules are, “It should be of technical and historical significance. It should be fun to drive. And it should be attractive to look at. If an automobile has those three qualifications, then it’s probably something that would be considered collectible.”

Someone with more than a hundred cars must have regretted some of the purchases, right? Leno doesn’t see it that way. He is a collector. His cars are all historical, so in his mind he can’t go wrong. If he buys a car that’s not valuable yet, it will be eventually. As it ages, it will become historical, and therefore collectible. In his words, “if you buy something that’s rare and valuable, it will always be rare and valuable.”

What does Jay Leno spend his money on?

Even though Leno has enough cash to live large, he lives a pretty normal life aside from his multi-million dollar car collection. Anyone who has seen his all denim outfits knows that he doesn’t spend money on clothes. He’s the first to admit he’s not interested in fashion. He doesn’t take expensive vacations, and in a lot of ways he still lives like he did at the beginning of his career

When Leno first came to Hollywood, he was homeless. He actually just hopped on a plane to LA with no plans for where to stay. Police would pick him up at night for wandering the streets, and once they even put him in the back of a police car right in front of the spot where his Hollywood star now sits. 

There’s not much more to Leno than jokes and cars. He’s a simple guy, and he knows what he wants. He has his three rules for cars, and he also has rules for where he will and won’t perform. He seems to know himself well, almost as well as he knows cars.