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Ferrari’s model year at the 2014 Pebble Beach Concours d’Elegance

The Pebble Beach Concours d'Elegance Classic Car ShowThe Pebble Beach Concours d'Elegance Classic Car Show
The 1954 Ferrari 375 MM Scaglietti Coupe owned by Jon Shirley is driven onto the winners ramp after being named Best of Show during the 2014 Pebble Beach Concours d'Elegance in Pebble Beach, California, U.S., on Sunday, Aug. 17, 2014. The annual event, now in its 64th year, raised a record $301.9 million in 2013, the highest total for a series of classic car auctions anywhere in the world. Photographer: David Paul Morris/Bloomberg via Getty ImagesPhoto by David Paul Morris/Bloomberg—Getty Images

Ferrari is a brand that hasn’t had many bad-hair days since its birth in 1947 (if I forgive the company for the 1980s-1990s Mondial era, that is). In fact, the latest record amount paid at auction for a car was the $38 million a 1962 Ferrari GTO commanded at this year’s Bonham’s auction at the Quail Lodge during the Pebble Beach Concours week.

But for all the adoration, accolades, authority in motorsports and sports cars—and yes, elitism—the Prancing Horse has never, until now, won the Pebble Beach Concours’ Best of Show trophy, arguably the most important judged vintage-car event on the calendar and one that quantitatively adds value at resale. It’s also been 46 years since a post-WWII car took the top slot.

And so, this August, when the the winning car turned out to be the 1954 Ferrari 375 MM Scaglietti Coupe owned by Jon Shirley (ex-Microsoft CFO), the news flash-fired around the globe. The sinuous ex-Rossellini two-seater had shattered two firsts at once—make and model year. (The filmmaker had commissioned the car for his wife, Ingrid Bergman, as a wedding present; Ferrari created a unique color, now known as Ingrid gray, for it, while accenting the interior with lipstick red.)

I have a particular affection for the car: In the late ‘90s I participated in a road rally, the California Mille Miglia. Shirley, too, competed that year, in the 375 MM. I will never forget laying eyes on it for the first time and feeling the automotive equivalent of true love. Many years later, the car’s insanely beautiful lines still haunt me; I often use a variant of the car’s name as an online password.

The 375 MM wasn’t the only big Italian O of the concours, however. For the first time in history, 20 of the 21 250 Testa Rossas made from 1957 to 1958 came together. After the GTO, the 250 Testa Rossa is considered the second most desirable Ferrari. As one longtime Pebble Beach judge commented on them: “These are Ferraris made when Testa Rossa was still two words” (the 1980s Ferrari Testarossa is a different breed altogether). Such rarities are owned by lords, Laurens and McCaws, among others (the royalty of car collecting). But the real news was the heart-arresting, outrageous sight of so many together at once. Each is a work of art, each is a snowflake, each is sex on wheels. I’ll shut up and let you feast on the gallery.

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A couple of other, non-Italian highlights from this year’s Pebble Beach Concours:

The 1952 Jaguar XK120 Open Two Seater—a terribly stodgy name for a blinding bullet of a race car. The bubble-topped Jag made a rare U.S. showing—its owner is Swiss—as did factory test driver, 92-year-old Norman Dewis, who in 1953 piloted the car to 172.4 mph to set a speed record. No comment on his twinkle-eyed reference to having had a little bourbon on board.

The 1934 Hispano-Suiza Coupe de Ville and 1934 Hispano-Suiza Coupe Chauffeur. These fraternal twins, with coachwork by the esteemed firm Fenandez et Darrin, were originally commissioned by Gustav de Rothschild, a member of the eponymous banking family. The long flowing lines and teardrop bodies made them some of the best eye candy on Pebble’s 18th hole.