Throughout its 68-year history, Ferrari has made some of the greatest cars the world has ever known. But if you had to pick the greatest era, just one period where the company could do no wrong, it would have to be the ’50s and ’60s. No disrespect to the La Ferrari, Enzo, F40, Daytona, Dino, or any of the mid-engined greats that have come since, but no company before or since had a run quite like Ferrari at mid-century. Back when every car it built was sexy and chrome-bumpered, the line between road cars and racers was permanently blurred, and every car that rolled out of Maranello was beautiful. When cars like the Testa Rossa, California, GTO, and Lusso weren’t just museum pieces for billionaire collectors, but real machines driven by movie stars, and world-class racers alike.

They were the cars that gave the Ferrari brand its beguiling sense of romance, and effortlessly capture an essence that the company has tried to hold onto in the six decades since. And while these mid-century cars might not look like they have much in common, many of them are variations on a common theme. For as different in style and temperament as they all were, many were built on either a long-wheelbase (LWB) or short (SWB) chassis, had the legendary Colombo V12, which was the jewel in Ferrari’s crown from 1947 to 1986, and were all sold under the “250″ model designation.

Especially during the company’s early years, Enzo Ferrari looked at his road cars with contempt. Scuderia Ferrari was founded in 1929 to win races, not to build cars. The company initially competed Alfa Romeos, but was forced to build its own cars when Alfa took control of its factory racing team. After World War II, the company rebuilt its destroyed factory and launched the 125 S road car in 1947, which Enzo believed he could sell in order to fund the racing team. The Ferrari road cars of the 1940s were coarse, cobbled together with parts borrowed from race cars, and had old-fashioned styling that looked like it came out of the pre-war era. But Ferraris kept winning races, and people kept clamoring to buy them, so Enzo reluctantly kept building road cars.

By the early 1950s, the company’s road cars were becoming must-haves among Europe’s elite, and with it came Ferrari’s evolution into the company we know today. In 1952, the company first teamed with Battista “Pinin” Farina for body design. While the company was working with a number of coach builders (a holdover from the pre-war era), Pininfarina soon became the company’s design partner of choice, and created a partnership that still endures. With the Colombo V12 now bored out to 3.0 liters, and healthy relationships with Italy’s other premier coach builders (including Scaglietti, Zagato, and Vignale, among others) lined up, the 250 was launched in 1953, and was the most powerful and refined model the company had ever built.

Like the Ferraris that came before it, the 250 cars had their initial success in racing, but with gorgeous looks, and seemingly limitless power, they began to catch on in a big way. The first Ferraris built for the U.S. market came in 1954, and quickly became the car of choice for Hollywood’s biggest names. By the end of the decade, the radically styled 250 Testa Rossa had come to dominate racing, and as the ’60s dawned, the 250 GT was desired as a luxury grand tourer as it was an internationally-feared racer.

Between 1960 and 1965, Ferrari dominated international racing, taking the 24 Hours of Le Mans every year, with 250 variants taking four of those six victories. Launched in 1962, the 250 GTO was one of the most accomplished (and feared) racers of the era. With its lightweight aluminum body and V12 tuned to 300 horsepower, it dominated international GT-Class racing. It was so good, in fact, that it continued to win even as rivals switched over to a mid-engined design. Not to be outdone, Ferrari followed it up with the 1963 250 P, which had its powerplant mounted amidships. By 1965, however, the 250 cars began to show their age, and newer cars with bigger Colombo engines took their place in the company’s lineup.

Back in the beginning of the decade, an owner of two 250s personally complained to Ferrari about his cars’ clutch issues. When he took these issues to Enzo Ferrari, he was given the brush off. Angry and offended, the man decided to build a car that would beat Ferrari at his own game. The man’s name was Ferruccio Lamborghini, and by 1966, his mid-engined Miura supercar spelled the end of front-engined flagships, and kicked off the wave of mid-engined Italian supercars. Since the early ’70s, nearly every big Ferrari has had its engine mounted amidships, and the Ferrari versus Lamborghini rivalry is one of the most entertaining in the automotive world.

It’s been 50 years since Ferrari built the last of its 22 different 250 variants, for a total of just over 2,300 cars. But their legend looms larger over the prancing horse brand than ever before. They represent the first truly successful marriage between Ferrari’s unmatched racing pedigree with its world-class elegance and luxury, and as the collector car market has spiraled out of control, some of these cars are now worth more than their weight in gold. A 1962 GTO that sold in August 2014 for $38.1 million holds the record for most expensive car ever sold at auction. An unrestored California Spider (the model immortalized in the 1986 movie Ferris Bueller’s Day Off) sold for $18.5 million in 2015, and a 1957 Testa Rossa sold for $16.3 million in 2011.

While they’re all cars that unquestionably blend art with engineering, it’s almost a shame that they’re so valuable. It means that the majority of them will end up as museum pieces, blue chip investments, and status symbols locked away to be ogled by the world’s wealthiest, their tremendous power and handling being consigned to history as they become all but impossible to insure. In short, the 250 cars have become what Enzo Ferrari feared: cars to be looked at, not driven.

Follow Derek on Twitter @CS_DerekS