Leno: The best cars are the ones with great stories

The thing I like about my taste in cars is that I have no idea what it is. Really, if I had to define it, I would say I like to buy a good story more than I like to buy a particular vehicle. I’ll tell you what I mean with a couple of recent purchases.

About a year ago, I got a call from an elderly woman—and by elderly, I mean probably in her 90s. She tells me she lives in Beverly Hills, three miles from my house, and that she and her sister were roommates with Marilyn Monroe before Marilyn was famous. There are pictures of her with Marilyn and everything. She has a 1966 four-door Lincoln Continental convertible that she bought brand-new, with all the options except FM radio, because FM cost extra and she didn’t know if FM was just a fad or would stick around, so she didn’t want to pay for something that might not be here in a couple of years. She asked me if I wanted to come see the car.

Honestly, my first thoughts were: That’s a giant car, it’s 53 years old, and it probably needs everything. Do I really want it? But I had to go look at it.

Well, I go to her house, and although I wouldn’t say it was a brand-new 1966 Lincoln, it looked like maybe a four-year-old 1966 Lincoln. There were a couple of supermarket dings because she used to go from the Beverly Hills Country Club to the hairdresser to the grocery store to home. She must have put about a thousand miles a year on it, because it was showing 60,000 miles. Otherwise, everything looked and worked perfectly. I drove it around the block, and it drove perfectly, too. It also sat right, like a girl who had gone to finishing school. This Lincoln handled like a bowling ball on a water bed, but it was so much fun to drive. I loved this car, and I really had no choice. I had to buy it.

Now, I admit stuff does kind of find me, because people know I don’t flip anything. I hear a lot from old guys—and by old guys here, I mean people my age—who call up and say, “I just want it to go to a good home.” Nobody wants to sell something and then see it later in one of the auction catalogs for three times as much and feel like an idiot. But I really do go for the stories.

A while back I got another call, from a guy 93 years old. “Jay!” he shouts, “this is Leo Pupkin! I’ve got a ’67 Chrysler Imperial, two-door, Crown, dual air conditioners front and back! You should come take a look at this car!” I say, “Okay, where do you live?” He says, “Sunset Boulevard!” I say, “Where on Sunset?” He says, “Beverly Hills!”

So now I’m William Holden, driving out Sunset to the old mansion. It’s right near the Beverly Hills Hotel, a pretty ritzy neighborhood, and as I go up the drive, the gates open to a long driveway. I pull up to the house, and I’m greeted by this elegant fellow in a smoking jacket with an ascot, plus another gray-haired guy.

Leo says, “This is my mechanic! He’s serviced this car every month for me here at the house, but he’s retired, and I can’t drive it!” Turns out Pupkin was a movie producer, and he made African American films for African American audiences when films were segregated. He’s taking me through his house, and the décor probably hasn’t changed since maybe 1953. It’s immaculate, but very old. We head out to the garage, and Leo says, “Before I show you the car, if you want the car, you gotta take all this crap!” He opens the garage door, and there, in boxes, is every spare part for the car you would ever need. There are spare wiper motors, spare window mechanisms, extra switches—everything. Just in case the car ever broke, he didn’t want to be stuck.

Again, I wouldn’t say the car was a brand-new 1967 Imperial, but it was pretty darn close. It had 140,000 miles on the odo, and Leo had had it serviced by his guy every month, so it’s immaculate. It took me right back to high school because it was the car Mr. Drysdale drove in The Beverly Hillbillies—even the same color, gold with the black roof.

Well, now I have to buy it—the story is just too good. And in my experience, if there’s a good story, it’s usually a pretty good car.

The article first appeared in Hagerty Drivers Club magazine. Click here to subscribe to our magazine and join the club. 

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    I have 1991 limited edition xjs Jaguar 12 cylinder in great shape but I never see anything about them. I saw Jay recently found a clear and is renovating it. Would love to see it completed.

    OH! how I miss my black-on-blue suicide Lincoln. I got it in return for a Chevy Manza, what a deal! We had another gas crisis brewing at that time so the car sat for quite a bit, wish I never let it go.

    A while back I made a presentation on why I collect cars. During the creation of the presentation, I discovered that nearly every car I own had a unique story either how I acquired it or its own story. My most recent was a 1914 Moyer bought from an estate. The deceased, age 95, died 12.21.2021, owned the car since 1957. He and his wife drove it in many tours and in 1995 he put the car up on blocks inside a trailer which he put in a barn and it too on blocks and padlocked the trailer. It never came out of the trailer until I bought it in March of 2022! I have the name and business of the original owner then there is a gap until 1951. That owner sold it to the man whose estate I bought it from.


    Great article!
    Would you be interested in a 2002 Lexus SC430 Neiman Marcus Edition? I own number 17 of 100. Only 35k miles!

    I love these old car stories as these cars become family members and live in your heart forever.
    The car that really lives in my heart was my Aunt and Uncles 1938 Chevy two door sedan that my cousin and I grew up with.
    One of the many memories I have in that Green machine was riding down Broadway in San Diego the morning of December 7th 1941 as we took my Uncle Pete, a Chief in the Navy to his waiting Destroyer.
    The whole family was in that Chevy.
    There were Sailors running down Broadway and my Uncle yelled out “What Ship you on, Get On!!. By the time we time we reached the pier we had Sailors on the running boards, the back back bumper and sitting on the front fenders and that Chevy never missed a beat. They kept the Old Chevy until sometime in the late 1960’s. My cousin drove it to college and i often wished they could have kept it and restored it.
    I’ll always wonder what ever happened to it and if it is still maybe tooling along on some roadway today.

    Being a third-generation car/dealer son and an owner of a vintage Chris-Craft, I have to say that it seems to be axiomatic that the more distiguished the car or boat model, the more distinguished the back-story. It must be nice to be Jay to attract so many high-end pieces that seem to come with high-end tales and presumably high-end prices!
    Have fun!

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