Money can't buy you happiness, so they say, but it can buy you a piece of automotive history at Monterey Car Week, if you have enough of it. Each year, at the country's most prestigious gathering of classic cars, collectors take note of everything that crosses the block at Pebble Beach's myriad auctions. Here are the top earners at Monterey that have had the ultra-rich digging deep into their pockets over the years.
Sold for: $38.1 million in 2014
Talk about pedigree: This particular 250 GTO Berlinetta made a name for itself as a competitor and a winner, before ever falling into the loving hands of collectors. With under 40 ever produced, it's no wonder that the 250s top this list—and it holds the record for the most expensive car to ever be , in Monterey or otherwise.
Sold for: $27.5 million in 2013
Until the sale of the 250 GTO Berlinetta, this '67 275 GTB soft-top held the record for of a non-race car in the United States. Anyone who puts down eight figures for an automobile should be able to dispense related trivia, like an explanation for the 275 GTB's seemingly unintelligible suffix (which stands for "North American Racing Team").
Sold for: $26.4 million in 2014
What makes this 275 GTB different from some other fine Ferraris to in Monterey? Like fine artwork, it's been cared for and preserved, and it belongs to a very prestigious and rare lineage. Oh, and because it took third at Le Mans in 1965. Try saying that about most modern garage-queen collector cars.
Sold for: $17.6 million in 2015
Like some of the others in this cadre, this Ferrari 250 LM was coach-built by Scaglietti, adding to its prestige and . For some perspective, see below for how much a McLaren F1 sold for, just the same year. It's reported to be number 23 of 32 produced, making this list some-thing of a homecoming for a storied few Italian superheroes.
This Ferrari comes from an era when "California" evoked images of endless summer and drop-top weather: a dream for most of us. The lucky owner of the '61 250 GT California Spider is likely in a dream world of his own. Don't think of it as worth half as much as the 250 GT that sold for $38 million—envision this spectacular convertible as the smart-money investment.
Sold for: $16.5 million in 2015
What has a V-12, a 4-speed manual, disc brakes, and all of its paperwork in order? This 1962 Ferrari 250 GT, a short-wheelbase coupe, painted a gorgeous cerulean. It slips in just under , in line with the average sale price for the vehicles with the highest price tags. In addition to having taken top honors at concours events in past years, the 250 GT is reported to have served as personal car of Mr. Bertone himself. Come prestigioso!
Sold for: $16.4 million in 2011
Diversity is one of the only characteristics separating the most exclusive cars, and this Ferrari Testa Rossa is rolling proof. When it sold for in 2011, it set a new auction record—not just in the U.S., but the world over. Today, its "low" price tag likely reflects the sentiment of a nation coming out of recession—hey, even a billionaire has to eat—and the '57 Testa Rossa could become even more valuable while off the block.
Sold for: $15.2 million in 2014
There are only so many variations in the lineage of the Ferrari 250 GT, and a collector pays dearly to own the exact one that he wants. Of the 56 Scaglietti-built 250 GTs, only 37 had covered headlights, and this California Spider is among them. A bonus item, most definitely included in the , is a "rare and desirable hardtop." You know, in case you take out the weekend car and it starts to rain.
Sold for: $13.8 million in 2015
Of the classic cars that earn their keep the most in Monterey, only one isn't a Ferrari. But this McLaren F1 is hardly showroom-spec (or as off-the-lot as McLarens get): It started life as a road-going F1 before undergoing a conversion to the vaunted LM spec (this is not one of the original six F1 LMs), including those models' bespoke V-12 and aero equipment. Was the new owner satisfied with the purchase? Likely, as the F1 was of Monterey mere hours after the transaction.
Sold for: $13.2 million in 2015
Last, but certainly not least, is a Ferrari 250 GT Tour de France: the curvaceous hardtop progenitor of Ferrari's most memorable cars of the last century. Like so many of the other highly collectible Ferraris on this list, was entered as a race car multiple times, including stints at the eponymous Tour de France and the Rome Grand Prix. Just because the TdF's sale price was lower than some of the others here, that doesn't mean it isn't worth a buck. It's the '50s model that set the tone for the even more desirable '60s models.