The sky blue ’56 Continental Mark II glints like something from the set of Mad Men. One of the most expensive cars of its time, the Mark II saw only 2,550 produced. “It looks like a piece of jewelry,” gushes Dale Matthews, owner of Matthews Memory Lane Motors. The dealership displays dozens of collector cars, ranging from a black 1915 Ford Model T to a yellow 2002 Chrysler Prowler.

Cars are not just an occupation for Matthews but a lifelong romance, beginning in the late 1940s when he was an Oregonian newsboy watching Buicks, Cadillacs, and Henry’s V8 Fords hurtle down 82nd Avenue. “Eventually I could tell a Hudson from a Mercury from three blocks away,” Matthews wrote in his autobiography, Every Deal’s Different.

At age 12, Matthews entered the car business, washing used Packards, Oldsmobiles, and Fords at Rathbone’s Cars for $7.50 a month. At 13, he bought his first used car, a ’31 Chevrolet two-door sedan, for $35. Later, in his first new car, he spent nights “dragging the gut,” racing other drivers across the Burnside Bridge to downtown and then south on Broadway.

Meanwhile, Matthews worked his way up to salesman, head mechanic, general manager, and, by age 19, co-owner of Tom & Dale’s Used Cars, City’s Youngest Car Dealer. In 1979, he opened Matthews Car Company at SE 52nd and Foster with eight collector cars.

As his inventory grew, so did his reputation. In 1994, he bought Memory Lane Motors at SE 26th and Holgate, his current location. Outside, a local muralist painted his most notorious acquisition, a ’30 black custom-bodied Lincoln rumored to be involved in a Portland socialite’s homicide. (“Every car has got a story,” says Matthews.)

His business has withstood car thefts, shotgunned windshields, and outré client requests. One came in 1994, when his right-hand man forded the Willamette in a ’66 Amphicar—a German land-water hybrid—to verify the car could float. (He was lucky; other Amphicars sank like anchors.)

Matthews, who turns 77 this December,  has sold more than 10,000 collector cars, including a 1916 Buick to a 96-year-old man in 2017. “Most people have an inexplicable desire to have their first car again,” Matthews wrote. “Or have their father’s car, the first one they learned to drive. That year, that make, that model, and that color.”

He keeps 14 personal cars in his private heated garage, including his company mascot, a ’36 Ford, “Rodney the Roadster.” One of Matthews’s original poems, engraved in brass and mounted on the dashboard, begins, “On this little car / there is not one part / that I don’t love / with all my heart.”