Calling it the Mona Lisa of the automotive world is not an exaggeration. Like Leonardo’s subject, the old Roller isn’t an exquisite beauty, but its significance goes beyond purely aesthetic attributes. Chassis No. 60551, registered on the road as AX201, demonstrated its reliability on a 3218-kilometre run, forever earning the marque a reputation as “the best car in the world.”

Rolls-Royce Motor Cars’ parent company, the Volkswagen Group, sold it to a private collector last year for a reputed $105 million-plus, a not unreasonable sum in the grand scheme of things for the most famous car in British motoring history. The notion of AX201 coming to market again someday suggests that those with the resources and the urge to acquire it should put a note to themselves on the refrigerator.

Bugatti’s Type 35—also produced in A, B, C and T variants—was the most successful race car from the French marque, garnering more than 2,000 motorsport victories from 1924 to 1930, among them the 1926 Grand Prix Championship and first-place finishes in the Targa Florio for five years in a row.

The diminutive racer was powered by a 2.0-litre inline-eight engine (larger in the 35T) that, when eventually supercharged, developed 100kW; an impressive figure for the day. Not so impressive was Bugatti’s insistence on cable-actuated brakes—uncompetitive with then-new hydraulic brake systems—which founder Ettore Bugatti reputedly defended, saying, “I make my cars to go, not to stop.” Still, a Type 35 is a treasure in any collection.

The big blower Bentley, so named because of its supercharger, won the 1928 24 Hours of Le Mans and further established the reputation of W.O. Bentley’s brutes as being the fastest trucks of their time. Bentley chassis wore bodies from a variety of coachbuilders, with its motorsport cars earning the company a reputation for rugged durability and speed.

The antithesis of their lithe, nimble French and Italian competition, the 4½ Litres were the heavyweight champions of their day. About 720 examples were produced from 1927 to 1931, 55 of which were supercharged and developed a whopping 179kW in racing form. Driving one improves one’s biceps.

With only four built between 1936 and 1938, and just three extant, the remaining examples of the SC Atlantic are some of the most valuable cars in the world. Though with many other Type 57 models made from 1934 to 1940 in coupe, two-door, four-door and convertible form, Bugatti dreamers can aspire toward a Type 57 of less rarified provenance.

Beneath the long hood of each was a 3.3-litre inline-eight derived from Bugatti’s Type 59 Grand Prix car. Powering the aerodynamic SC Atlantic, it gave speed to the fluid shape that expresses the spirit of Art Deco and makes it the greatest Bugatti ever, though proponents of the Type 41 Royale may demur.

Surely Italy’s greatest prewar automobiles, the Alfa Romeo 2300, 2600 and 2900 series commanded a presence on tracks across Europe throughout the entire reign of Alfa’s most powerful cars. The 2900 and 2900B models, with 2.9-litre, Vittorio Jano straight-eight engines, were primarily developed for endurance in competitions like the Mille Miglia and 24 Hours of Le Mans. A number of coachbuilders—mostly Italian—crafted bodies in long- and short-chassis versions, with Carrozzeria Touring creating some of the most desirable. Whether one prefers an elegant streamlined coupe or dashing low-slung roadster, the 8C 2900 in any form was an Italian dream car more than a decade before the first Ferrari was ever made.

French Talbot-Lago developed its T150-C for racing, using a 104kW, 4.0-litre inline-six in a light, low-slung SS (super sports) chassis featuring independent front suspension. One model expressed French streamline design unlike any other and is, according to some opinions, the most beautiful car ever made.

Launched at the 1937 Paris Motor Show, its body was by French coachbuilder Figoni & Falaschi, who produced Talbot-Lago “Teardrops” in two series; the latter showcased in New York features an uninterrupted fastback profile. Eleven examples of those were made, and on the rare occasion one comes to market, it commands formidable interest and a price commensurate with its rarity.

Derived from the successful Mercedes-Benz W194 race car of 1952, the street-going 300 SL raised every bar for engineering, build quality and performance. With its mechanically fuel-injected inline-six and the ability to reach a top speed of 262km/h, it delivered performance unmatched by any other car of the period.

The “Gullwing” coupe, built from 1954 to 1957, was followed by a roadster in 1957 until 1963. While the roadsters are more user-friendly, the Gullwing remains the most iconic model in the history of the Silver Star. Exactly 1400 examples were made—enough to fill a space in major car collections around the world—and the fact that this blue-chip collectible can still run with contemporary automobiles makes it more astounding still.

The wickedly elaborate tubular space-frame chassis that gives this Maserati its unofficial name was made up of more than 200 thin steel tubes, making it lighter and stronger than conventional race cars. Made to compete at Le Mans, Tipo 60 and 61 models were respectively powered by front-mounted 2.0- and 2.9-litre inline-four cylinder engines, tilted over at a 45-degree angle for a lower centre of gravity.

Despite the brilliant engineering of Giulio Alfieri and drivers like Carroll Shelby, the car was plagued with reliability issues. Of the 22 examples made from 1959 to 1961, none are identical, and today, imposters abound, so provenance is king.

With only 75 made, Aston Martin’s DB4 GT is on the radar of many well-heeled collectors. But those with four times the budget will be seeking a DB4 GT Zagato, the most desirable Aston of them all. A shorter-wheelbase version of the street-going DB4, the GT Zagato was made for competition, and features a drop-dead gorgeous body penned by Zagato’s Ercole Spada and hammered by the carrozzeria in Milan.

Not a single one of the 19 originals made between 1960 and 1963 looks identical to the other, but any one of them will gain entry to the most exclusive concours or—for the brave—vintage racing event. Continuation examples made by Aston Martin satiate the need of collectors not able to acquire one of the originals.

Corvette enthusiasts point to Chevrolet’s 1963 Sting Ray as proof that America could design a car as breathtaking as anything coming from Europe, while outperforming them as well. The shark-like, split-window coupe was designed by Larry Shinoda, inspired by preliminary concepts done a few years previously by colleague Peter Brock. Under the Corvette’s fibreglass body was a 327 ci V-8 engine that, with Rochester fuel injection, made 268kW.

Examples ordered with the Z06 special performance equipment package also featured a bigger fuel tank for racing, and with only 199 examples made, they are the most desirable C2 coupes among the almost 10,600 made in 1963. Today, few sports cars from the era are as rewarding to drive. And for cost, reliability and performance, no car from the 1960s beats a ‘Vette.

Aston Martin’s DB5 connection to Agent 007 saved the company’s financial bacon at a time in the early 1960s when the small manufacturer was teetering on the verge of bankruptcy. With that model, the marque became synonymous with the film franchise.

Made from 1963 to 1965, the DB5 evolved from the DB4 Series V and is distinguished by an aluminium 4.0-litre inline-six engine and a stunning aluminium body designed by Italy’s Carrozzeria Touring. With 886 examples, there are enough for many would-be Bonds clamouring to have a DB5 in their garage. One well-regarded restorer even related finding a Goldfinger cassette in quite a few DB5s in the shop for a restoration. The example pictured here once belonged to Paul McCartney.

Upon first seeing one, Enzo Ferrari called it “the most beautiful car ever made,” a claim that’s hard to argue. Debuted as a coupe and roadster in 1961, the Jaguar E-Type was designed by Malcom Sayer and appeared light-years ahead of its bulbous predecessor, the XK150 (ignoring the rare D-Type racers and XK-SS models sandwiched in between).

The Series 1 XK-E, with its covered headlights, elegant tail lamps and thin bumpers, looks best, and the earliest “flat-floor” models made through 1962 are the collector’s preference. The powerful inline-six engine was enlarged from 3.8 litres to 4.2 litres in 1964, and carried on through 1967. That it’s powerful, drivable and relatively reliable counts for much, considering that nothing this exquisite in appearance—coupe or roadster—deserves to be so user-friendly.

Some guy named Shelby stuffs a Ford V-8 into a lightweight aluminium British roadster and creates magic. Raw, unrefined and just plain stupid fun, the Shelby Cobra is the automotive equivalent of Miesian reductionist architecture, and proof that “less is more.” No sports car better asserts the spirit of the American hot rodder.

In its era, when brute power and handling finesse were mutually exclusive objectives, the Shelby Cobra delivered both, proving to be a formidable foe on street and track. Introduced with a Ford 260 ci V-8 in 1962, it was soon replaced by Ford’s 289, while the 427-powered monster came along in 1965. For owners who want to really drive, the 289-powered, rack-and-pinion Mark II models are the way to roll.

Ford garnered its most famous racing victory at Le Mans in 1966, when Ferrari’s American nemesis finished first, second and third with the Mark II version of the radical GT40. Its low profile—a mere 100cm high—hinted at sports car–design trends to come. Ford 289 ci V-8 engines originally powered the mid-engine racer, but a big-block 427 V-8 shoehorned into the Mk II proved the secret to success in long-distance events like Daytona and Le Mans.

Built from 1964 to 1969 in Mk I through Mk IV versions, about 105 examples were made in total. The little-known Mk III was for road use only, and of the mere seven made, one was owned by conductor Herbert van Karajan. Talk about Ride of the Valkyries, albeit a cramped one for anyone much taller than the maestro, who topped out at 5 feet, 8 inches.

Any of Ferrari’s 250 GTOs would seem the obvious choice for a Dream Machines garage. But one model launched in 1964, while not the fastest or the rarest of the Ferraris, is the quintessential road-going GT of its era. With its covered headlights, shark gills and upturned Kamm tail, the 275 GTB is beautiful but burly, and does that front-engine V-12 “thing” like no other car.

Bodies designed by Pininfarina and made by Scaglietti adorned a range of twin- and four-cam models, totalling more than 800 examples, including some rare racing versions. The 275 GTB/4 (from 1966 through 1968), of which 330 were built, is the most collectible, unless one covets one of the ten 275 GTB/4S NART Spiders made in 1967.

The Lamborghini P400, named Miura after the Spanish breeder of fearless fighting bulls, shook the automotive world when first seen parked in the Monte Carlo Casino Square in 1966. With 762 produced from that year until 1973, in three successive series of P400, P400S and P400SV, the Miura is the quintessential low-slung, two-seat Italian sports car of the 1960s.

The first road car to feature a transversely mid-mounted V-12, it was undeniably beautiful, thanks to a timeless body designed by Bertone’s Marcello Gandini. Unquestionably the most collectible Lamborghini in the marque’s history, it is the inspiration for every Lamborghini model made since. The prize bull is the P400SV, made from 1971. Every Miura cabin is a snug fit; a diet and stretch classes for some prospective owners may be in order.

Really, any early 911 is great, but the 1973 RS hits the sweet spot. Light, nimble and rare, it is the model that every 911 nut wants, for good reason. Built as a race car for the road, the RS was developed for homologation into Group 4 of the FIA’s motorsport classification system, though the company sold sufficient numbers to qualify for Group 3 Grand Touring homologation.

Essentially a hopped-up 911S, it carries a 2.7-litre flat-six engine that makes 156kW and is good for about 241km/h. Its look is unmistakable, distinguished by a chin spoiler, a ducktail rear spoiler and the now-famous Carrera script along its side. In addition to a few original homologation cars, 1,360 Touring and 200 Lightweight examples were made, the latter being the most desirable of the bunch.

Perhaps more rewarding to look at than to drive, the Lamborghini Countach is still the poster car to beat. Chances are, more kids went to sleep dreaming about a Countach than any other car in history. The successor to the Miura had a V-12 engine positioned longitudinally behind the two-seat cabin, and the space-age shape was the work of master designer Marcello Gandini, whose Lancia Stratos Zero show car of 1970 ushered in the wedge that dominated car design for almost two decades.

Fewer than 2,000 Countach examples were made through 1990, and of those, the first series LP400—with 158 built from 1974 to 1977—is the purest in form and the most collectible, by far. The bloated 25^th Anniversary Edition models, from 1988 through 1990, recall Elvis in a white leisure suit.

If Porsche is getting a lot of parking spaces in our Dream Machines garage, it’s only because the marque’s cars are so deserving. With its extraordinary power, the 959 charted the course for the modern 911. Created in the early 1980s to compete in the Group B rally series, the 959 soon developed into the ultimate Porsche road car.

Powered by a water-cooled, sequentially turbocharged flat-six engine derived from the 962 racer, the 959 also incorporated technical advancements, like all-wheel drive, that led Porsche road cars into the 21^st century with the 964 series Carrera 4. Officially produced from 1986 to 1988, a few stragglers left the factory through 1993, for a total of 345 examples made, according to some sources. By every standard, the 959 is still considered modern today; back then, it was something from another planet.

Today, the performance of Ferrari’s first supercar pales in the shadow of later models like the Enzo and LaFerrari. But the F40 was a game-changer for the Prancing Horse. Like its immediate predecessor, the 288 GTO, the F40 set the stage for the future with a mid-mounted, twin-turbo V-8 engine—the first for a road-going Ferrari—which has become the dominant configuration of Ferrari sports cars today.

Pininfarina designer Leonardo Fioravanti appropriated styling cues from his 288 GTO, distilling them into a shape that was purposeful, pure and unadorned. With 1,315 examples built between 1987 and 1992, the F40 is a must for those with an itch for the last project initiated under the direction of Il Commendatore himself, founder Enzo Ferrari.

There’s really nothing else to say; this three-seat wonder is certainly the most fastidiously engineered car of the 20^th century, and is the supercar by which all others will forever be judged. Of the 106 examples made between 1994 and 1998, 65 were road-going versions, with others built for competition in various states of tune and trim.

What set the F1 apart was its designers’ no-compromise approach to concept and execution. Gordon Murray and Peter Stevens realized a three-seat Formula 1 racer for the road, delivering speed, finesse and safety in a tidy package that looks as modern today as it did when new. With a top speed of 386km/h, it remained the world’s fastest car for well into the mid-2000s. Eye-wateringly valuable today, a McLaren F1 is the crown jewel of any supercar collection.

Yes, it’s déjà vu, as Porsche comes back to mind with the most evolved air-cooled 911 of them all. The last model powered by the oil-and-air-inspired flat-six engine—made from 1994 to 1998—is also the best performing, and a car that so many original owners wish they had never, ever sold.

The wide-body C2S, C4S and Turbo models are the best looking of the bunch, and of those, the rare 1997 Turbo S (year unknown on the example pictured here) is the gold standard. Unicorn hunters may go on safari for a Euro-spec Carrera RS or GT2. Any 993 one chooses is sure to be a weekend plaything of choice.

The Bugatti marque was resurrected in 1998 during the reign of VW’s chairman, Ferdinand Piëch. The aim was to build the ultimate luxury supercar. His vision came to life with the Veyron, launched in 2005 and powered by an 8.0-litre, quad-turbo W16-cylinder engine. Making 736kW, it set the production car speed record in 2005 with a speed of 408.46km/h.

Robb Report created a new category in its Car of the Year contest, voting it Car of the Decade in 2010. Grand Sport, Super Sport and Grand Sport Vitesse variants were built through 2015, by which time the engine developed 883kW. A total of 450 units were produced across all models, a staggering number considering the price of admission to the Veyron Club. Not exactly thin on the ground, there should be plenty available on the gently used market for years to come.

Featuring a carbon-fibre chassis and optional carbon-fibre wheels—the first in the industry—the mid-engine Koenigsegg CCX was designed to conquer the supercar market with a twin-supercharged, 4.7-litre V-8 engine developed and manufactured in-house. Combining 806 hp and serious attention paid to aerodynamic efficiency, the slippery supercar could reach 100km/h in 3.2 seconds and achieved a top speed of more than 394km/h.

Setting the stage for the Swedish marque’s future models, such as the record-setting Agera RS, the CCX was a limited-production masterpiece built from 2006 to 2010. Only 49 examples were produced over four model variants; including the CCXR Trevita that featured elaborate diamond-weave carbon-fibre and developed a whopping 760kW. Its price of approx. $6.5 million was as staggering as its performance.

For those who want an Italian supercar whose name ends in “i” but doesn’t begin with “F” or “L,” the rare offerings of Horatio Pagani should fill the bill. The Huayra Roadster, named for an ancient South American wind god, resembles its coupe predecessor but somehow, remarkably, weighs less. But then it does have an aerodynamic carbon-fibre body—built with surgical precision—that is claimed by the manufacturer to produce 816kg of downforce.

The Huayra Roadster is powered by a mid-mounted 6.0-litre Mercedes-AMG V-12 engine that develops 562kW. Production has been underway since 2017, and is limited to 100 examples. A substantial price of approx. $3.6 million ensures that the model will command a prime spot in any supercar collection for quite some time.