The eve of the Best Supercars 21st Century’s was marked by a palpable sense of uncertainty and impending shift. As is often the case with hundred-year cycles, mankind was facing all manner of cataclysm and possibility on the edge of this new era, from the threat of doom of the Y2K bug to the promise of a bright new millennium.

The supercar microcosm is a sort of mechanical barometer that offers insights into societal trends. Though infinitesimal compared to the auto industry at large, supercars can serve as a proverbial hemline index during unsure times, four-wheeled canaries that speak to the coalmine of the human experience. At their most exuberant, exotic automobiles are unrestrained expressions of lavish style and freewheeling possibility witness the unapologetic ally sexual curves of the 1960s-era Lamborghini Miura or the boggling engineering excess of the 1980s-era Porsche 959. And when malaise prevailed during the OPEC oil crisis years in the 1970s, automakers followed suit with a paucity of compelling offerings and emissions-strangled flagships.

As history unfolded into the early aughts, top offerings from the boldest of carmakers adhered to their own historical totems rather than succumb to the devastating September 11, 2001 attacks. Ferrari, planning to celebrate the hallowed name of its notorious founder, produced the V-12-powered Enzo from 2002 to 2004, building only 399 examples of the insectoid flagship.

Porsche made use of an aborted Formula 1 engine and a Le Mans prototype platform to launch the Carrera GT, an ambitious 10-cylinder–powered two-seater with a near half-million-dollar MSRP that languished in showrooms towards the end of its 1,270-car production run. The brilliance of the decidedly analog Porsche only recently earned the respect and confidence of the most committed brand fanatics in recent years, with some examples trading hands close to the seven-figure mark.

The 2000s marked the strident entry of large manufacturers who saw this rarified space as an opportunity to flex their engineering muscle and glamourize their brands. Is a supercar still super if it’s subsidized by a mainstream carmaker? The question splayed open for debate during this turbulent time, though there’s little arguing the industry’s benefits of deep pockets that stimulated this often tenuous niche. For starters, Ford sought to resurrect the glory of its string of legendary successes at the 24 Hours of Le Mans by rehashing their low-slung GT40 into a retro-modern stunner simply dubbed the GT.

The supercharged 550 hp model didn’t have a real-world race car equivalent that would arrive years later in the GT’s 2016 re-issue, whose competition counterpart reclaimed victory at Le Mans on the 50th anniversary of the original win. But the 2005 model was inarguably a supercar: the two-seater effectively channeled the neck-snapping spirit of its antecedent, and it had the snorty, edgy performance to match. That chemistry did wonders for Ford’s overall brand perception, providing a much-needed morale booster that would help buoy the company as it later struggled for its financial survival.

The Volkswagen Group crashed the supercar party with full force in the 2000s thanks to their acquisition of three iconic brands in 1998. The reinvigorated Lamborghini nameplate launched the Murcielago in 2001, introducing a new design language and modernist spirit. Though the wedge-shaped land missile barely sold over 4,000 units in its nearly decade-long run, the “Murci,” as it was dubbed by aficionados, marked Lambo’s first new design in over a decade.

Its newly engineered V-12 upheld the brand’s core values, while a new emphasis on engineering meant the whole package worked better than any Lamborghini before it. More significantly, the top model opened the floodgates for Lamborghini’s more affordable Gallardo, which would become the brand’s most successful model in history with over 14,000 cars produced. Not only did the German-funded Lamborghinis retain the brand’s signature outrageous styling, they introduced previously alien aspects like build quality and reliability.

Lamborghini wasn’t Volkswagen’s only power play for the new millennium. The conglomerate’s spending spree in the late 90s also involved the acquisition of Bentley and Bugatti, two slumbering nameplates whose mention evoked a whiff of long-lost British and French glamour. Bentley’s claim to fame had long been its elegant and swift grand tourers, a tradition that was reignited with the launch of the Continental GT in 2003.

The re imagined coupe clung to old world traditions of quilted leather and hand-inlaid wood veneers while devouring mile after mile of interstate with ease. It became an unmitigated success, selling nearly 70,000 units over the course of its lengthy production run. But that success also ignited an inevitable debate: do copious sales automatically void inclusion into the exclusivity of the supercar realm? A newly redesigned version of the GT arrived in 2018, an offering that aims to extend Bentley’s relevance well into the 21st century.

At the other end of the spectrum, there was no question of the specialness of the Bugatti brand when it resurfaced into production in 2005. Officially headquartered in the Alsace region of France but developed using German resources, the Veyron was pioneered as a cost-no-object celebration of all things excessive.

The term ‘Super’ was absolutely apt: the egg-shaped Veyron was motivated by no fewer than 16 cylinders, four turbochargers, and a seven-figure price tag. It pushed the limits of what passenger cars were capable of achieving, from its sub-3 second zero-to-60 mph time and 1,000 hp rating to its top speed in excess of 255 mph.

But it also tested the limits of its starry-eyed clientele: though only 450 Veyrons were produced in total (with later 16.4 Super Sport versions pushing 1,200 hp), it took an agonizing 10 years to sell through that paltry production run, begging the question of whether the world’s appetite for obscenely expensive vehicles was intrinsically limited.

The Chiron, the long-awaited sequel to the Veyron, offered increased power, more responsive handling, and more elegant styling. It also proved more desirable, selling with more vigor than its innovative but less stirring predecessor, a fact that lends more credence to a product’s pull than an audience’s automatic acceptance of a name brand.

Supercars and collector cars can be one of the most direct barometers of discretionary spending and emotional purchases. And though global financial crises have historically had a direct effect on the supercar market, the 2000s also saw a remarkable climb in collector car values. Despite the economic downturn in 2008, Hagerty says that collector cars outperformed the real estate and stock market between 2005 and 2009.

Particularly notable within the collector market is the Ferrari brand and its seeming imperiousness to larger scale trends. Though every bubble can and will eventually burst (including the Ferrari craze of the 1990s, which escalated when Enzo Ferrari’s 1988 death triggered rumors the brand might fold), the prancing horse brand has been enjoying an unprecedented run in the 21st century. Fueled by charismatic mechanical chemistry and limited production numbers, Ferrari has managed to defy the odds by continuing to create unprecedented demand for its sports and supercars.

While new models invariably invoke lengthy wait lists and hefty dollar signs above sticker price, classic Ferraris command an even dearer premium: a fabled Ferrari GTO, of which only 39 were built between 1962 and 1964, traded hands in 2018 for $48.4 million, making it the most expensive car ever sold at auction. The priciest car to privately exchange ownership was also—you guessed it—a Ferrari GTO that transacted for $70 million the same year. The long wait lists and limited production numbers of Ferrari flagships promise to continue the trend of high dollar future sales, though that exclusivity is under threat by the marque’s 2015 move to becoming a publicly traded company and their stated intentions for higher volume production.

While the 21st century rules of engagement may appear to have been dictated solely by major players, the supercar story is not always so cut and dry. As much as the big boys have solidified the marketplace with their economic, engineering, and marketing fortitude, a small but crucial element of the supercar world remains stoked by the inventiveness and independent spirit of a select few. There’s an element of the scrappy, edgy and artistic cheekiness that characterizes the spirit of these groundbreaking boutique cars.

Consider the case of two tiny firms formed in the fringes of the supercar power stream. Pagani was founded in 1992 by Horatio Pagani, a Lamborghini veteran who departed from the Sant’Agata carmaker when they stubbornly refused to embrace his suggested incorporation of carbon-fiber components. Recognizing the benefits of the strong, lightweight material, Pagani formed his own car company in Italy’s so-called Motor Valley, a stone’s throw from Ferrari and Lamborghini headquarters.

Unlike the household name manufacturers, Pagani embraced a counter intuitive engineering philosophy that has yielded some remarkably executed vehicles. Powered by Mercedes-AMG V-12s, Paganis have astounded both with their innovative engineering (which includes cutting edge implementation of carbon fiber and active aerodynamics), and their stunning visual style.

The shapes and textures recall the shock of the new when vehicles like the Lamborghini Countach first emerged on the scene head-turning, salacious, extreme. The reception has gotten no less rabid over the years, with each new model breaking fresh ground and shocking pundits anew. Complementing the novel mechanical bits are exquisitely finished details that betray exacting hand craftsmanship and an emphasis on traditional coachwork.

Similarly counterculture is Koenigsegg, a low volume Swedish builder that was established in 1994. The brainchild of Christian von Koenigsegg, the brand embraced extremely forward-thinking engineering and took a full eight years to build its first car, the 655 hp CC8S. Despite the lengthy process, its advances were so far ahead of its time that it only took one more year for the model to become recognized by the Guinness Book of World Records as the most powerful street legal car on the planet, in 2002.

Koenigsegg continued to disrupt the establishment with the release of the One:1, an extreme exercise in lightweighting that achieved a brutal 1:1 horsepower-to-kilogram ratio. Even more noteworthy was the 1,360 hp Agera RS’s shattering of the land speed production car record in 2017. The twin-turbo V8-powered RS took full advantage of a shut-down stretch of Nevada highway, peaking at a stunning 284.55 mph and averaging a top speed of 277.87 mph in two runs. The record upset the old guard Bugatti Chiron by a considerable margin, a startling reminder of how big-name manufacturers can be put on alert by whipsmart upstarts.

Nearly two decades into this century, the supercar appears to be thriving now more than ever, weaving a diverse and vibrant fabric of options across a myriad body layouts, engine configurations and styling directions. Bolstered by the momentum of an ever-growing upper class that can afford to upholster themselves lavishly in four-wheeled couture, the global appetite for supercars and their latest taxonomic spinoffs, hypercars, has afforded manufacturers the ability to dig deep into the wells of possibility and create increasingly complex and intriguing kinetic sculptures.

And while some critics might harken back to the heady days of the 1960s and cite a time when raw horsepower and knee-high, bumper-free bodywork was the order of the day, those traditionalists should also be reminded that safety features like crumple zones and anti-lock brakes were also woefully absent in those visual masterpieces.

Whether you credit the evolution of the breed or the inevitable march of progress, there is an undeniable element of wonder in the breadth and depth of exceptional vehicles available today, and the staggering performance they are capable of delivering. Add to that the double-win of hybrid drivetrains which use “torque fill” to create even fatter, more emotionally charged power delivery and you’ve got a perfect storm of speed, sexiness, and exclusivity, elements that come together to make our century the best of all supercar periods yet.