Jay Leno Takes A Look At Three Defining Icons Of American MotoringGuessing HeadlightsAndre NalinFri, September 11, 2026 at 7:30 PM UTCAdd us on GoogleImage Credit: Jay Leno's Garage / YouTube.Few things show how dramatically American cars evolved after World War II better than placing machines from the 1940s, 1950s, and 1960s side by side. Styling changed, performance exploded, and buyers' expectations changed almost beyond recognition in barely two decades.That's exactly what Jay Leno and automotive appraiser Donald Osborne did in the latest installment of Assess and Caress on the Jay Leno's Garage YouTube channel. Their subjects came from the Audrain Automobile Museum in Newport, Rhode Island.Representing the three decades were a 1947 Buick Roadmaster, a 1956 DeSoto Fireflite Sportsman, and a 1966 Oldsmobile 442. Each tells a very different story about what American buyers wanted from their cars at the time.AdvertisementAdvertisementLeno and Osborne didn't simply admire them, either. After digging into their design, engineering, and driving characteristics, the pair compared how values for similar examples have changed over the past five years.1947 Buick RoadmasterImage Credit: Jay Leno's Garage / YouTube.The Roadmaster featured in the video is a remarkably original 33,000-mile example, retaining its original interior despite portions of the exterior having been repainted. Its Harley Earl-penned styling originated before World War II, yet Osborne argued the design was remarkably forward-looking for its time.Power comes from Buick's Fireball straight-eight paired with a manual transmission. Osborne also praised the Roadmaster's road manners, recalling a relaxed drive through Rhode Island on two-lane roads where its character made far more sense than it would battling modern interstate traffic.Market values have treated cars like this surprisingly well. According to Osborne, a comparable Roadmaster might have been worth about $27,500 five years ago, while today it could require around $42,000.1956 DeSoto Fireflite SportsmanImage Credit: Jay Leno's Garage / YouTube.The DeSoto is almost the stylistic opposite. Finished in an eye-catching coral-and-charcoal color scheme, it embodies designer Virgil Exner's famous "Forward Look" and the optimism of 1950s American automotive design.AdvertisementAdvertisementUnder the hood sits DeSoto's own 330-cubic-inch Hemi V8, while gear selection is handled through Chrysler's wonderfully period-correct push-button transmission controls. Osborne noted that DeSoto's relative obscurity hasn't prevented mid-century styling from finding a new audience among younger collectors.That appears to have helped its value. Osborne estimated that a similar Fireflite Sportsman has climbed from roughly $55,000 five years ago to about $65,000 today.The Oldsmobile 442 Is Leno's FavoriteImage Credit: Jay Leno's Garage / YouTube.The 1966 Oldsmobile 442 takes the performance crown of the trio. This particular example features the rare factory L69 setup with three Rochester two-barrel carburetors and a four-speed manual transmission.Leno was especially enthusiastic about how usable the Oldsmobile still is today, saying he would happily drive it across the country. The triple-carb setup operates primarily on the center carburetor during normal driving before bringing the outer pair into play under heavier throttle.AdvertisementAdvertisementCuriously, market values haven't shared Leno's enthusiasm. Osborne said an equivalent 442 might have commanded around $85,000 five years ago but could be closer to $75,000 today.Three Cars, Three Different ErasThat makes the Buick the biggest percentage winner despite remaining the least valuable of the three. Leno still chose the 442 as the car he'd most want, followed by the unusually original Roadmaster and then the DeSoto.It's a useful reminder that collectibility doesn't always follow enthusiast preference. Each car represents a distinct chapter of American motoring, yet the market has rewarded them very differently — and sometimes in ways even experienced collectors like Leno might not expect.If you want more stories like this, follow Guessing Headlights on Yahoo so you don't miss what's coming next.
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