Only 18 cars have ever sold at auction for more than US$10 million, and 11 of them have sold during the Monterey Car Week auctions surrounding the Pebble Beach Concours d’Elegance in mid-August each year. A few weeks from now, that number will likely rise dramatically as there are 10 cars going to auction over the three day Monterey auction period that are estimated to surpass the $10 million barrier, and several that might achieve the milestone by rising from lesser estimates if more than one ultra high-net-worth individuals (UHNWI) has their mind set on owning them.

For most of us, it's difficult to understand why someone would pay the price of an island for a car not that much different to the 1,200,000,000 others on the planet’s roads? Putting that in perspective, if you earn enough to save $50,000 a year after tax, it'll take you 200 years to save enough for one of these cars (760 years in the case of the GTO record holder, but the bad news is it'll be worth a lot more by then and the really bad news is you won't be around anyway).

Here’s the list of cars that have achieved that feat, and if you follow the links, you’ll see they are astonishing beautiful, rare and usually have a storied history featuring prominent people. We keep an entire Top 100 list with descriptions and links on Gizmag and we're in the process of mining data to provide a great deal more.

The nine cars pictured above achieved the remarkable feat of selling with an eight figure price tag. A 1962 model of the fabled Ferrari 250 GTO ($38,115,000 @ Pebble Beach, 2014) is one of just 39 made and the only one to reach auction, Juan Manuel Fangio's 1954 World F1-title-winning Mercedes-Benz W196R ($29,598,265 @ Goodwood, 2013), a near perfect 1967 Ferrari 275 GTB/4 S N.A.R.T. Spider ($27,500,000 @ Pebble Beach, 2013), a 1964 Ferrari 275 GTB/C Speciale ($26,400,000 @ Pebble Beach, 2014), the barnfind 1961 Ferrari 250 GT Spyder California SWB ($18,465,733 @ Retromobile, Paris 2015), a 1954 Ferrari 375 Plus Spyder ($18,315,361 @ Goodwood, 2013), a 1957 Ferrari 250 Testa Rossa ($16,390,000 @ Pebble Beach 2011), a 1961 Ferrari 250 GT Spyder California SWB ($15,180,000 @ Pebble Beach 2014), and a 1964 Ferrari 250 LM ($14,300,000 @ New York 2013).

The next and final nine cars to broach the $10 million dollar mark are a 1953 Ferrari 340/375 MM Berlinetta ($12,745,707 @ Villa d'Este, Italy, 2013), a 1957 Ferrari 250 Testa Rossa ($12,187,280 @ Maranello, 2009), Baroness Gisela von Krieger's 1936 Mercedes-Benz 540 K Spezial Roadster ($11,770,000 @ Pebble Beach 2012), a 1964 Ferrari 250 LM ($11,550,000 @ Pebble Beach 2014), a 1960 Ferrari 250 GT Spyder California SWB ($11,275,000 @ Pebble Beach 2012), a 1968 Ford GT40 Gulf/Mirage Endurance Racer used in the film "Le Mans" ($11,000,000 @ Pebble Beach 2012), a 1961 Ferrari 250 GT Spyder California ($10,894,900 @ Maranello, 2008), Captain George Whittell's 1931 Duesenberg Model J coupe ($10,340,000 @ Pebble Beach 2011) and Steve McQueen's 1967 Ferrari 275 GTB/4 ($10,175,000 @ Pebble Beach 2014).

It would be easy to dismiss cars that are at the bottom of the "eight figure club" as worth less than those at the top. That's far from true, as the market has been so bullish since the Global Financial Crisis that many cars that are true masterpieces of automotive art and racing legend get buried by the ever higher prices of the last few years. Tenth place on the list above is a prime example. This 1953 Ferrari 340/375 MM Berlinetta, with F1 driver Umberto Maglioli at the wheel, famously averaged 222 km/h (138 mph) for the final 365 km (227 mile) stage of the infamous Carrera Panamericana to ensure Ferrari won the 1953 World Sports Car Championship – an all-time record for a public road stage that will likely stand forever.

The phenomenal growth of the collectible car marketplace in recent times is driving prices forever skyward and the 1961 Ferrari 250 GT Spyder California once owned by actor James Coburn (pictured above) is another illustration of the market growth. It's in 16th place in the above list and was the most expensive car ever sold at auction when we wrote it up in 2008 – all the other cars on this list have sold since. There's also a Bugatti Royale in our Top 100 listing which sold for £5,500,000 (US$9,666,250) in November, 1987 at a Christies auction in London. A decade or two from now, when we publish our $100 million dollar car listing, if the Royale ever comes to auction again, it will be in that list.

This year the number of outstanding collectible automobiles being offered at Monterey in mid-August is greater than ever before. Here's our rundown of the 10 cars that will achieve more than $10,000,000 (if they sell – cars in this bracket generally involve a reserve price), and a few "smokies" that are an outside chance to reach an eight-figure sale price.

1960 Ferrari 250 GT SWB Berlinetta Competizione

Official estimate: Contact RM-Sotheby's

Unofficial estimate: more than $17,000,000

Our comments: One of 45 aluminum-alloy-bodied Competizione versions built in 1960, this racing specification car was campaigned by Luigi Chinetti’s North American Racing Team (NART). Nine days after being born in Maranello, it finished seventh overall and fifth in class at the 1960 12 Hours of Sebring, driven by George Arents and Bill Kimberly (the heir to the Kimberly-Clark paper empire). Further racing success followed, but the crowning glory is the car as it now sits on the road. It recently underwent a complete concours-level restoration to original specifications by Motion Products Inc. at a cost of $700,000. Extremely rare, impeccably credentialed and near perfect.

1961 Ferrari 250 GT SWB California Spider

Official estimate: $16,000,000 to $18,000,000

Our comments: Currently owned by the colourful Lord Irvine Laidlaw, founder of the world's largest conference company (IIR) and owner of a fleet of the world's most desirable automobiles, including at various times, a Ferrari 250 GTO, Porsche 904GTS, Porsche 904/6, Maserati 250S, Maserati 6CM, Bugatti Veyron, Ferrari 275 GTB/C Berlinetta Competizione, Maserati Tipo 61 "Birdcage", and a works Jaguar D Type. Lord Laidlaw sold a sizeable part of his collection at an RM auction in September, 2013.

This particular car is very original according to auctioneers Gooding & Company, and "has not been the subject of a full restoration, nor has it made the rounds at various Concours’ d’Elegance, offering its new owner the pride and pleasure of being the 1st to exhibit this car at the most exclusive international events."

In addition to Lord Laidlaw's contribution to the provenance, it is believed to have been owned by Gunther Sachs, the prominent German playboy with family links to both Opel and Sachs. It's quite likely Gunther courted his second wife, Brigitte Bardot, in this car.

1964 Ferrari 250 LM by Scaglietti

Official estimate: contact RM-Sotheby's

Unofficial estimate: more than $15,000,000

Our comments: Fifty years ago, an LM won the race it was built to win (the 24 Hours of Le Mans, hence the name), becoming the last Ferrari to do so. Despite an extensive and very chequered (in a good sense) race history, this car has never had a major bingle and retains all of its original mechanical components. Formerly part of the Matsuda Collection, Ferrari Classiche certified, and shown at the 1964 and 1966 Earls Court Motor Shows, this "weapons-grade Ferrari", as the beautifully presented Pinnacle Portfolio catalogue terms it, ticks all the boxes.

Only 32 LMs were ever built, combining beautiful balance and handling with a 3,286 cc aluminum V12 producing 320 hp. LMs rarely go to auction, and those that do have made the top 10 global annual prices every time going back for two decades.

The world record price for a Ferrari 250 LM of $14,300,000 was set in New York at RM-Sotheby's Art of the Automobile auction in November, 2013 and a second 250 LM sold for $11,550,000 at Pebble Beach last year, with another 250 LM selling for $9,625,000 in Scottsdale earlier this year, so this car could potentially give the model three entries in the top 20 most valuable cars ever sold.

Cars like this rarely come to auction, with previous million dollar sales of the 250 LM fetching $7,014,433 (Maranello, Italy, May, 2008), $3,674,680 (London, U.K., October, 2008) and the three previous occasions are so long ago that auction internet links never existed: $2,310,000 (Lot 249) at RM's Amelia Island auction in March, 2000; $2,147,500 (Lot 24) at Christie's Pebble Beach auction in 1999 and $1,797,334 (Lot 172) at a Bonhams & Brooks auction in Gstaad, Switzerland in December 1998.

1962 Ferrari 250 GT SWB Berlinetta Speciale

Official estimate: $14,000,000 to $16,000,000

Our comments: There are no ugly cars that sell for more than a million dollars and in this category of $10 million plus automobiles, we’re somewhere near the intersection of automobiles and art, with a riveting back story mandatory. This is a genuine one-of-a-kind 250 GT SWB Berlinetta Speciale designed by a collaboration between Nuncio Bertone and a 23–year–old Giorgetto Giugiaro and built by Nuncio’s legendary house of Carrozzeria Bertone as his personal car.

Inspired by Ferrari’s "shark-nose" 156 F1 world-championship-winning Grand Prix car, with recognizable elements of the 330 TRI LM and 246 SP sports racing cars, the signature feature of Giugiaro’s design was its “shark-nose” front-end treatment.

A prime example of the coachbuilder’s art, the Berlinetta Speciale was introduced at the 1962 Geneva Auto Show, then at the annual carrozzerie exhibition at the Biscaretti Museum in Torino where it was showcased alongside Pinin Farina’s Superfast III, a Touring-bodied Maserati 3500 GT, and a Dual-Ghia L6.4. Auto Italiana.

A revised design was implemented by the time the car (3269 GT) was displayed as the centrepiece of the Bertone stand at the Torino Auto Show in November, 1962.

Despite all the accolades Nuccio’s Berlinetta Speciale received during its tour of the motor show circuit, Enzo Ferrari never formally acknowledged the car that had so beautifully re-imagined his classic 250 GT SWB, Bertone was never engaged by Maranello and Ferrari production cars remained built or designed almost exclusively by Bertone's Torinese rival Pinin Farina.

This car is being presented at public auction for the first time in its history and will almost certainly enter the top 10 most valuable cars ever sold at auction when the hammer falls on Sunday evening at Gooding & Co.’s official Pebble Beach auction.

1998 McLaren F1 "LM-Specification"

Official estimate: contact RM-Sotheby's

Unofficial estimate: more than $12,000,000

Our comments: The McLaren F1 is almost certainly destined for the same sort of superstardom as the Ferrari GTO on the auction block, being the most significant supercar of the modern era. The rationale behind this statement is clearly elaborated on in our top 100 cars article, but it boils down to its naturally-aspirated motor (still the fastest, non-forced-induction car ever), pioneering composite construction, drivability and racetrack success ad infinitum. The most valuable McLaren F1 of all will be the LM, because there were only five ever made (and the Sultan of Brunei bought two of them). This car is exceptional because, although it was the second-last road-spec F1 built, it was one of just two cars upgraded by McLaren Special Operations with an LM-spec engine. This means it retains its luxury interior and all modern conveniences, including satnav and the Extra High Downforce Package plus a Le-Mans-winning engine.

1959 Ferrari 250 GT Comp Alloy Berlinetta

Official estimate: $9,000,000 to $12,000,000

Our comments: Estimated by Bonhams to sell between $9,000,000 and $12,000,000, this car might well sell for more as it is one of the legendary seven "interim" cars (in the transition from the 250 GT TdF Berlinetta to the 250 GT SWB Berlinetta) and has been the subject of a no-expense-spared restoration. Such a restoration included finding and purchasing the original motor, sending the chassis to Ferrari where Vaccari e Bosi (the original chassis builder) restored the chassis while Modena's Carrozzeria Autosport Bachelli & Villa did the body.

Last year was an eventful one for this car as it received Ferrari Classiche certification and appeared at both the Concorso d’Eleganza Villa d’Este (pictured above) and the Goodwood Festival of Speed (pictured below).

In 2015, it took out the Platinum Award Class I Excellence Cup at the Palm Beach Cavallino Classic, an Excellence in Class at Mar-a-Lago and Best Ferrari at the Greenwich Concours d'Elegance.

We'd give you details of previous auction results for this ultra-rare model if there were any, but there aren't. The "interim" model is so coveted that they tend to be kept for long periods by those that have procured them, and those that have changed hands, have done so privately.

1956 Ferrari 250 GT Berlinetta Competizione "Tour de France"

Official estimate: contact RM-Sotheby's

Unofficial estimate: more than $11,000,000

Our comments: Only 77 of Ferrari's "Tour de France" models were ever built, with every one sold in the last five years fetching more than $3,000,000 and the two most recent highlights being a 1956 model which sold for £4,872,000 ($7,862,554) in London last September, and a similar car which fetched $6,710,000 during Monterey Car Week in 2012.

This isn't just any Tour de France model, though – this is the car that gave the model its name through winning the 1956 Tour de France Auto, an automotive equivalent to the famous bicycle race that predates it by four years and indeed, was France's equivalent to Italy's Mille Miglia or Sicily's Targa Florio.

The car is one of only seven Scaglietti-bodied first-series competition berlinettas, but in historical terms, it is even more significant because it was owned and raced by one of motorsport's larger-than-life figures, the Marquis Alfonso de Portago.

Born to a long line of Spanish nobility that included famous explorer Álvar Núñez Cabeza de Vaca, de Portago’s grandfather was the Governor of Madrid, and he was named for his godfather, Alfonso XIII, the last King of Spain.

High-testosterone males are a family tradition, and de Portago’s father led a famously hedonistic existence, but it paled in comparison to the handsome, dashing, unspeakably wealthy, devil-may-care young Marquis.

Alfonso was an accomplished equestrian and considered one of the world’s leading steeplechasers in 1951-52, competing twice in the Grand National Steeplechase at Aintree, but he was far too large to become a jockey. His ability to conquer new challenges is best illustrated by his brief affair with the sport of bobsledding, where he learned the sport’s nuances in roughly two weeks in order to lead the Spanish national team to the 1956 Winter Olympic Games. With de Portago steering, the two-man bob finished fourth, missing out on a medal by 0.16 seconds. A year later he took the bronze medal in the world championships at St Moritz in the same event.

Portago's sporting exploits were more than matched by his legendary womanizing. He married New York socialite Carroll McDaniel in 1948 at the age of 20. Though the couple had two children, the Marquis could never resist the lure of the feminine chase, and he was known to be a regular philanderer. His courtships of Revlon spokesmodel and one of the first supermodels, Dorian Leigh (said to be a partial inspiration for Truman Capote’s Holly Golightly character from Breakfast at Tiffany’s) and actress Linda Christian (the first "Bond girl" on a television version of Casino Royale) were his most high-profile affairs, though the more you read of his exploits, the more rampant the philandering appears to have been.

De Portago began midget car racing in Paris in 1953 and a chance meeting and instant rapport with Scuderia Ferrari driver Luigi Chinetti at the Paris Salon de l'automobile in October 1953 considerably accelerated his participation in the sport. The famed North American Ferrari importer invited Alfonso to be his co-driver at the infamous Carrera Panamericana to be held two weeks later. He accepted Chinetti’s offer and his adrenalin addiction reached new levels as he watched Chinetti pilot a Ferrari 375 Plus across 2,000 miles of Mexican roads at breakneck speed from the passenger seat.

Portago immediately purchased his own 4.5-liter Ferrari and in January, 1954 claimed second place outright in a Ferrari 250 MM at the 1,000 km of Buenos Aires. Rather than rise though the rankings, de Portago took a meteoric leap and a year after sitting beside Chinetti as passenger, he retired from the 1954 Carrera Panamericana when his Ferrari 750 Monza broke down – he was in the lead at the time.

A month later, de Portago placed second at the Venezuelan Grand Prix in a Ferrari Monza, behind Juan Manuel Fangio’s Maserati 300S. Fangio would later say of de Portago, "I considered him one of the most courageous of all the racing drivers … a good driver and an excellent comrade." In December 1954, barely 12 months after his first ride as a passenger in a race car, the swashbuckling Marquis took three victories at the Bahamas Speed Week.

In early 1956, de Portago became an official Scuderia Ferrari driver, enabling him to campaign an assortment of Ferraris (857 S, 860 Monza, 500 TR, and 625 LM) as well as getting access to purchase one of Maranello’s new 250 GT racing berlinettas, (this car – 0557GT), in which he won the Tour de France Auto and Coupes du Salon, as well as the Coupes du USA in April 1957. That's de Portago pictured on his way to winning the Tour de France Auto in this car below.

De Portago's outsized personality played well in the media, where he was endlessly quotable, and his regular "punch ups" made for great newspaper headlines. By the time of his death while competing in the 1957 Mille Miglia, he was widely considered to be among the best drivers in the world. He competed in just five Formula One Grands Prix, with three DNFs, a fifth and a second place in the 1956 British Grand Prix, a drive he shared with Peter Collins.

While de Portago tempted mortality once too often, his legend and this car have endured, been restored to concours condition, and it has won first in class at Pebble Beach and Meadow Brook, the Prix Blancpain Award at the Louis Vuitton Concours d’Elegance and a Platinum Award at the Cavallino Classic.

The auction description calls this car a "once-in-a-lifetime opportunity to acquire one of the most historically significant competition Ferraris of all time" and that pretty much sums it up – TdF models rarely appear at auction and this one last saw the auction block at a Brooks Olympia (UK) sale in November, 1992 when it sold for £528,000 (US$802,560). It might be a long time until it comes around again.

1959 Ferrari 250 GT LWB California Spider

Official estimate: $9,000,000 to $11,000,000

Our comments: Sold new in 1959 to Prince Alvise Hercolani of Bologna, this car (1307GT) was one of 50 LWB California Spiders built by Ferrari. After six months of ownership, Hercolani sold the car to German F1 driver Wolfgang Seidel, and the ownership lineage is fully recorded to 1999 when the car underwent a complete resoration at Carrozzeria Autosport, Bacchelli & Villa in Italy. In 2004, the car was stripped to its bare metal and refinished in dark blue with silver hardtop, the same colors it sported during Seidel’s ownership.

The car was shown at the Meadow Brook Concours d’Elegance in 2005 and the 2008 Pebble Beach Concours d’Elegance before another $115,000 was invested to take it to Ferrari Club of America Platinum award-winning standards. Ferrari specialist Greg Jones was commissioned for a complete motor and suspension rebuild, and the entire car was detailed to concours standards before being shown at the Cavallino Classic in 2011. At this time, the car was certified by Ferrari Classiche and confirmed to be matching numbers throughout.

1953 Jaguar C-Type Works Lightweight

Official estimate: $9,000,000 to $12,000,000

Our comments: There were just 53 C-Type Jaguars built. Three lightweight works cars (of which this car is one), and a run of 50 cars to satisfy customer demand after the factory cars finished first, second and fourth in the 1953 Le Mans 24 Hour event. The biggest difference to the competition were the disc brakes. Endurance racing was born to demonstrate reliability and validate new automotive technologies for the masses and just as it has done more recently with hybrid and diesel drivetrains, Le Mans heralded the coming of age of a new braking technology with this car and its works siblings.

The winning C-type was the first to average more than 100 mph for the 24 Hours of Le Mans (105.8 mph, 170 km/h), and this car, which finished fourth, also broke the ton, averaging 104 mph (167 km/h).

Equally at home in any of the world’s finest concours or vintage rallies, this car represents a landmark in Jaguar history.

1950 Ferrari 275S/340 America Barchetta by Scaglietti

Official estimate: $7,500,000 to $10,000,000

Our comments: One of nine Scuderia Ferrari (factory race team) barchettas from the 1950s, this 12-cylinder Lampredi-engined car was one of only two Works Ferraris of its kind ever built. It was a factory Mille Miglia entrant in 1950, then subsequently competed under the Scuderia Marzotto banner in the 1951 and 1952 Mille Miglia, the 1951 Targa Florio and the sports car race at the 1952 Monaco Grand Prix. It was raced by such luminaries as twice-F1 champion Alberto Ascari, Giovanni Bracco, and Gianni Marzotto. The car was shown at the 1950 Salon de l'Automobile in Paris by Ferrari and the auction description tells its full history, including how it came to be owned by a 14-year-old automotive enthusiast who translated his love for vintage cars into a thriving restoration business. It's a great story, an incredibly important Ferrari and a rare chance to own a car of such historical gravitas.

1982 Porsche 956

Official estimate: $7,000,000 to $9,000,000

Our unofficial estimate: Could crack the $10,000,000 mark if the right gentleman racer wants to go racing in fashion.

Our comments: This car finished second in the 1982 Le Mans 24 Hour Race in the hands Jochen Mass and Vern Schuppan, taking part in the iconic 1-2-3 victory (pictured above), then served as the Porsche team’s top car for the remainder of the season, primarily driven by Ickx, Mass, and Bell. In September and October of 1982, this car (956-003) won the last three World Endurance Championship (WEC) races (Spa, Fuji, and Brands Hatch) of the WEC season and a non-championship race at Kyalami (South Africa), securing the WEC Drivers’ Championship for Ickx and the Manufacturers’ Championship for Porsche.

It returned to Le Mans in 1983, starting in seventh position on the grid behind the two other Rothmans Porsche entries (956-005 and 956-008), but won the race in thrilling fashion (read the catalogue description), leading a near-whitewash of the results and enabling the inspired and famous Porsche advertising poster that many readers might remember from the day (pictured below).

As the auction description says, "Among the Most Important Porsches in Existence."

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