"The guy was a contractor. He died of a heart attack. He had bought two Cadillacs owned by Waylon Jennings about 10 years before. The other one was a dark brown Seville with gold trim.
"White was the most popular color for Eldorado convertibles in those years," Hebb said. "I saw this one and it looked good."
In addition to the back seat monogram, Hebb has paperwork to prove the car had once been owned by the country singer with such hits as "Good-Hearted Woman" and "Amanda" and who teamed with country legend Willie Nelson on "Mamas Don't Let Your Babies Grow Up to Be Cowboys" and "Luckenbach, Texas."
Taped to the left rear window is a Tennessee vehicle registration renewal dated Oct. 11, 1983. It listed the owner of the Caddie as Waylon Jennings, 1117 17th Ave., South, Nashville, Tenn. The renewal fee paid was $45.
On the right rear window is another Tennessee Department of Motor Vehicles document that said Jennings had transferred the car to his son, Buddy Jennings of the same address. It was dated Oct. 3, 1984.
The white Caddie has been on the road more than any of the nearly 40 cars in Hebb's vintage fleet. For more than three years, it has carried local dignitaries in parades in Hagerstown, Waynesboro and Greencastle, Pa., from the Mummer's Parade to Christmas parades to Memorial Day to the Fourth of July.
Alvey Ford of Hagerstown, a long-time friend of Hebb's, borrows it to haul fellow members of the 29th Division Association in Hagerstown in area parades.
"It's a real parade car," Ford said. "It's a nice little car."
Little may be a bit off the mark when it comes to the size of the old Detroit behemoth. The Eldorado convertible, which rolled off the Detroit assembly line for the last time in 1976, weighed 5,000 pounds, stretched over 19 feet and is sometimes referred to as the "Eldosaur."
It cost $7,681 new.
"It was so big that when you went over a hill, you couldn't see the road anymore," said Ellen Ternes of Waynesboro, a member of the Prom Queens.
The queens are six local women friends who get together once a year, dress in campy 1950s prom gowns and "do the town," Ternes said.
"Our motto is there's no such thing as too much hair spray or too much glitter," she said.
Last year, the women decided to add charitable work to their night out. They asked Hebb if they could borrow the Jennings convertible so, at the annual cancer benefit auction, they could auction off a night on the town with the prom queens.
"We raised $375," Ternes said.
The top bidders were a local attorney and his retired judge father.
"We drove all around town with the top down. The Cadillac was a big hit," Ternes said.
Hebb sees the Cadillac as just another car in his collection. It's not his favorite.
"I don't have one," he said.
Hebb, a life-long car dealer, sold Buchanan Auto Park, a Chrysler-Jeep dealership east of Waynesboro, in 1998. He opened the first Toyota dealership in the Tri-State area in 1964.
He's been dealing with cars since he was a kid and has been collecting antique and classic stuff for 15 years. Some of the cars in the collection were traded back to his dealership, like an original, super clean, rust-free 1972 Toyota Corolla. He sold the car new to a local woman.
"It only has 39,000 miles on it," he said.
His oldest car is a 1917 Ford Model T; the newest is a 1997 Plymouth Prowler. In between are the average and not-so-average models of the American road from the 1920s through the 1970s.
Hebb owns Dodge roadsters and touring sedans from the Flapper era, Fords built during the Depression, a pristine, maroon '48 Chrysler convertible and a rare '49 Willys Jeepster.
He has a couple of 1950 Ford sedans, several high-finned Chrysler Corp. cars of the mid-and late '50s, two early Mustangs, some Thunderbirds, a sleek '55 Studebaker and a red, '55 Dodge pickup he sold new to a man in Mercersburg, Pa.
Hebb buys his cars at estate sales, auto auctions and from private individuals. All are for sale, but buyers need deep pockets to drive one away.
All are welcome to come in and kick tires, but only one in 50 buy, Hebb said.