While lots of people come to gawk at the insanely gorgeous cars on the lawn at the Pebble Beach Concours d’Elegance every August, there are also plenty of men with very deep pockets who come to do some serious shopping. There are a few blue-chip auctions during Monterey Car Week, of which the headliner is the three-day event produced by RM Sotheby’s. This year they’re also staging an auction-within-an-auction, with one of the world’s best car collections, called the Pinnacle Portfolio, going up for sale. RM is billing it as “the most significant and valuable private automobile collection ever presented at a single-day auction,” including everything from early model Ferrari race cars to the final production Enzo, gifted to the late Pope John Paul II.

In addition to the 25 Pinnacle cars, which include both classic and modern machines, are some of the most expensive and desirable cars in the world are set to cross the auction block. Top of the class is a 1953 Jaguar C-Type Works race car (top photo), which finished fourth overall at the 24 Hours of Le Mans in 1953, and is the second of only three “Works Lightweight” cars ever built by Jaguar in thin-gauge aluminum. It’s expected to bring in $9 million or more, making it one of the world’s most expensive Jaguars. It’s easily the most beautiful car in the sale in our opinion, though the competition is fierce – the 1950 Ferrari 275S/340 America Barchetta by Scaglietti (below) isn’t exactly an eyesore either. It could fetch $8 million-plus, in case you were wondering.

One of the most important competition Ferraris ever to be offered at auction, it started out as one of only two 275S Barchettas built, and was campaigned for the factory by legendary Italian racing driver Alberto Ascari in the 1950 Mille Miglia. There are dozens of Ferraris in the sale spanning several decades of production. Next to the 275S/340 America we’d place the bright yellow 1960 Ferrari 250 GT SWB Berlinetta Competizione from the Pinnacle stable. Prepared as a North American Race Team (N.A.R.T.) car, it competed in the ninth annual 12 Hours of Sebring in Florida just a few days after leaving the factory. RM calls it “the finest performing and best looking SWB in the world” – and this one could go as high as $17 million. It’s hard to choose favorites from the full roster of RM’s Monterey monsters, but we’ve waded in and done it for you, so scroll down for the rest.