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It might not surprise you to hear that Jay Leno began his working life running errands for a foreign luxury car dealership. He was the self-described “lot boy” who delivered Mercedes, BMW, and Rolls-Royce cars to customers. But slightly more surprising is that it was actually the dealership job that was instrumental in kicking off Jay Leno’s comedy career that culminated in hosting The Tonight Show.

Jay Leno got to deliver Mercedes, Rolls-Royce, and BMW cars for the dealership

Closeup of Jay Leno smiling while driving a 2004 Bentley S2 Coupe
Jay Leno in a 2004 Bentley S2 Coupe | Paul Harris/PacificCoastNews via GettyImages

Jay Leno says he was into old cars from the time he found and fixed an abandoned one in his hometown: Andover, Massachusetts. After saving money from summer jobs, 14-year-old Jay Leno bought a 1934 Ford pickup truck.

Leno wrote in Hagerty that he found himself attracted to a dealership called Foreign Motors on Commonwealth Avenue in Boston. The young enthusiast walked into the garage and announced, “I’m the new guy” and the mechanics there immediately found work for him.

Three days later, someone figured out that no one had officially hired Leno. But he must have been doing good work, because they kept him on. That’s how Jay Leno dealership career began.

Leno ended up doing new car prep. He also delivered the BMW, Rolls-Royce and Mercedes-Benz cars Foreign Motors sold. He did not know it at the time, but the cars’ eccentric new owners would leave as lasting an impact as the exotic cars.

Jay met “all kinds of weird people”

Jay Leno gives the thumbs-up while in a 1931 Bentley.
Jay Leno driving a 1931 Straigh 8 Bentley | Paul Harris/BWP Media via Getty Images

Jay Leno’s career at dealerships may have been inspired by beautiful classic cars, but he would remember the eccentric car owners he met for decades.

Sometimes it must have taken all Leno’s self-control to act like these eccentric folks were not. One especially wealthy family ordered Rolls-Royces often, and on one trip they asked Leno to pick up a family member. She hopped in the brand new car with a baby lion.

Leno was able to laugh off his encounter with the lion cub, and even found a tennis ball for it to play with after he dropped the car off. To his dismay, the tiny creature flattened the ball. The woman explained that she got a new cub every six months. The Rolls-Royce cars with shredded interiors made much more sense to Leno.

The young Leno made connections with some of his customers. The Boston orchestra conductor, Arthur Fiedler kept in touch. In fact, he called Jay to drive him around often. It took some getting used to when he called Leno everytime a Boston building caught on fire because he wanted to go and watch the firemen put it out.

“I enjoyed it, and it was great fun, partly because selling those kinds of cars meant you were always meeting all kinds of weird people.”

Jay Leno

Jay Leno’s dealership job kick-started his comedy career

Jay Leno steering a white Jaguar convertible into a driveway.
Jay Leno driving a Jaguar XK120 | Noel Vasquez via Getty Images

In addition to delivering new cars, Jay Leno had to pick up the brand-new Rolls-Royces when they rolled off the boat in Elizabeth, New Jersey. He would drive them 200 miles to Boston where the dealership would put them right on the showroom floor.

But Leno had some interest in standup comedy. And thanks to his job at the dealership, he now had plenty of material. So on his way home, he would stop at Improv in Manhattan to try out a comedy set. Soon Leno was hooked.

One time, a New York City customer ordered a new Rolls-Royce Corniche and insisted in paying with cash. So Jay Leno tucked a paper bag with $34,000 into his pocket, went to the docks in New Jersey, picked up another brand new car, and drove into Manhattan.

He parked the brand new car in “the worst part of Hell’s Kitchen,” walked into the club, and took the stage. Then he set the bag of cash on the piano and told everyone it was his “lunch.”

Jay finished his set and said he heard “all the people laughing.” Then he got in the Rolls Royce and drove all the way to the Connectictu tollbooth before realizing he had forgotten the cash.

Leno booked it all the way back to the comedy club and, miraculously, the money was still on the piano. Jay Leno pursued his comedy career and continued to collect cars. Today he’s as eccentric, and as respected, as the people he once delivered luxury cars to.

See Jay Leno reunite with a 1960s Rolls-Royce in the video below:


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