Here is your 2019 Hagerty Collector Car Madness Bracket

As much fun as it is to argue with your uncle at family reunions about your favorite cars, the conversation is ultimately about as productive as trying to locate that missing 10-mm socket. Commendable, but pointless. What if there were some way to settle the matter, perhaps by matching up cars from a variety of demographics against one another in a totally unscientific, bracket-style showdown?   

Well lucky for you, that epic clashing of automotive delights is Hagerty’s 2019 Collector Car Madness. To settle the score between beloved cars popular with Boomers, Pre-Boomers, Gen X, and Millennials, we are pitting each demographic against each other and asking you—our adoring readers—to vote on the Hagerty Facebook page in a series of 1-on-1 polls to determine which vehicles advance from each round. As the results roll in, we’ll update the bracket and lay out new matchups for later rounds of the tournament.

So if you are willing to declare to the entire Internet that you think the Bentley Turbo R is the greatest car of our entire 16-vehicle roster, you should first take a good hard look at your life, and then you should vote so your voice can be heard.

To determine which cars made our list, we selected a few cars that Hagerty insurance data indicated are especially popular within each age group. We also inserted a handful of wild card vehicles to keep things interesting, and made sure to seed each vehicle appropriately in their respective demographic “regions.”

Click on the image above for a full image of the bracket, print it out, and fill in your predictions. Post them in the comments, and we’ll see whose powers of prediction are most attuned. Without further delay, here are your 2019 Hagerty Collector Car Madness matchups:

BOOMERS

(1) 1963–67 Chevrolet Corvette vs. (4) 1997–2002 Plymouth/Chrysler Prowler

Chevy’s encore to the original Corvette is when an American sports car became the American sports car. There is no “bad” C2 Corvette—each year improved little by little, and there’s no doubt that the futuristic ’60s Vette look was a worldwide benchmark for design. To this day, many consider the one-year-only 1963 split-window to be the most gorgeous sports car of the era. The C2 Corvette also had a new chassis, independent rear suspension, and—of course—yearly offerings of optional high-performance V-8 engines.

Does the beloved Sting Ray lie awake at night worrying it’ll be unseated from the throne of American automotive icons by the Plymouth Prowler? Probably not. Still, the Prowler was an important vehicle for Chrysler in the late 1990s, as a poster child for the brand’s renewed design and styling energy, as well as a grand experiment for lightweight materials like aluminum. Hot-rodders did not take the V-6 Prowler seriously, but the retro-machine was nonetheless widely considered a success for Chrysler at large, even after Plymouth folded. Looking back, it’s an exceptional moment in automotive history where a shocking concept car actually made it to production with its ethos intact.

(2) 1968–70 Dodge Charger vs (3) 1965–70 Shelby GT350 Mustang

Adored as the villainous bad-guy ride in Bullitt and then celebrated for its perpetual penchant for never-meaning-no-harm shenanigans as the orange General Lee from Dukes of Hazzard, the second-generation Charger reeked of bad attitude. Which is why people loved it. The fact that the ’68 Charger’s Coke-bottle shape was way more attractive than the first-gen car didn’t hurt, despite still riding on the humble Dodge Coronet’s platform. People still go wild for Hemi-powered Chargers, and of course there is still big demand for four-speed cars, as well as unique colors like Panther Pink and Plum Crazy from 1970.

This will be be a tough matchup for the Charger. America loves the Ford Mustang, but there’s an even stronger deep-seated wonder and affection for those pony cars blessed by the hand of Carroll Shelby. Using Hi-Po 289-powered 2+2 fastbacks as the base for the original ’65 GT350, Shelby and his crew went to work packing the car with extra goodies to take output from 271 to 306 hp, and the GT350 benefitted from comprehensive lightweighting, improved braking, and track-tuned suspension upgrades. GT350s are perhaps the most universally desirable and appreciated Mustangs of all, and it is unquestionably the vehicle that cemented Shelby’s legacy as an American performance legend.

PRE-BOOMERS

(1) 1928–31 Ford Model A vs (4) 1985–97 Bentley Turbo R

One of the most widely enjoyed pre-war cars out there, the Ford Model A is an obvious choice as a top seed for the Pre-Boomer generation. When enthusiasm for the Model T was winding down in the late 1920s, Edsel Ford convinced his father to green-light a replacement with modern looks and technology that could ensure the Blue Oval could compete with mounting competition. The Model A got an all-new inline-four engine with gobs more power, the car was easier to drive than the previous T, there were a range of color choices and body styles, and starting at $460 it was still generally affordable. Ford sold nearly 5 million Model As over its production run, and many of these cars are still enjoyed today in a variety of forms, incuding hot rods.

The Bentley Turbo R is just about the polar opposite of the relatable, everyman Ford. Envisioned as a high-performance, better-handling take on the Mulsanne Turbo, the Turbo R was a major show of renewed engineering prowess from the British brand. Along with the Bentley’s updated dampers, stiffer anti-roll bars, and wider tires, it still had a lovely 6.75-liter turbocharged V-8 engine making an estimated 300 hp. We say “estimated” because Bentley never officially released power figures for the Turbo R or the Mulsanne on which it was based. When you’re buying a car that costs $195,000, it’s simply bad manners to discuss crass specifics like engine output. Power was adequate—not to worry, ol’ chap.

(2) 1955–57 Chevy Bel Air vs (3) 1987–93 Cadillac Allanté

Considered a seminal moment in American styling, the 1955–57 Chevy Bel Air is a permanent fixture of 1950s culture that endures to this day. The car’s exuberant look is nothing short of iconic, but it was the available overhead-valve small-block V-8 under the hood that made the Bel Air a sensation. Starting at 265 cubic inches and growing to 283 for 1957, the small-block in its many forms presented the opportunity to have Corvette power in a family vehicle. On top of the Bel Air’s flair and extensive powertrain options, it came in several body styles—convertible, two-door sedan, four-door sedan, two-door Nomad wagon, four-door Nomad wagon, two-door hardtop, and four-door hardtop. There’s truly a Bel Air for everyone, and these cars are to this day easy to find, customize, and maintain.

The Cadillac Allanté is indicative of a much less celebrated moment in General Motors history, but nevertheless one that is impressively ambitious. Cadillac bravely took on the two-seater luxury market in the late 1980s, hoping to steal away customers from the Jaguar XJ-S and Mercedes SL. Based on a shortened Eldorado frame, Allantés were assembled and painted at famed design house and coachbuilder Pininfarina, and then flown on specially customized 747 jets to Hamtramck, Michigan, for finally assembly. High cost and early reliability issues meant the Allanté was ultimately not a sales hit, although by the time the Northstar V-8 engine arrived in 1993, Cadillac had dramatically improved the car with several convenience and performance features—it was just too little, too late. All that said, the car’s looks are really starting to grow on people as ’90s cars in general become more popular. These two-seat Cadillacs remain rather affordable to acquire, and there is a lively, enthusiastic owner’s community, as well.

GEN X

(1) 1967–69 Chevy Camaro vs (4) 1950–67 VW Type 2 Transporter

By the time the ’67 Camaro finally hit showrooms, GM had its work cut out. The Ford Mustang was already out for a couple of years—to much fanfare—and there was clear demand for another pony car in the market. And we’ve now had the pleasure of watching the rivalry rage on for more than 50 years. When the Camaro launched, Chevy wasted no time introducing performance models, including the track-oriented Z/28 developed with 1967 SCCA Trans Am road racing in mind. By 1968 the Z/28 was available for street use, and there were tons of customizable options so people could spec out their Camaros to their liking, often with sporty pretensions. A renewed, more brawny look came with the 1969 Camaro, along with available four-wheel disc brakes. Today the Camaro retains its performance legacy, boasting a world-class chassis and truly potent powertrains—and it all started with the ’67.

Though it’s about as far as you can get from a sports car, the Volkswagen Type 2 Transporter can bring a smile to just about anyone’s face. The VW bus just brims with personality, and its legacy as a staple of 1960s counterculture is still with us today. Even in 2019, VW buses are in high demand among young people with dreams of traveling America, living the simple life detached from civilization in a Westfalia camper van. Although they’re not exactly bastions of perpetual reliability, as with the Beetle parts are affordable, widely available, and Type 2s are mechanical simple for the amateur wrench. With some TLC, these big VWs can run for a long time under generous use. The world over, Type 2s are sure to win you approval, spark conversation, and unleash a flood of memories from onlookers.

(2) 1966–77 Ford Bronco vs (3) 1978–87 Buick G-Body

If there’s one vehicle that stands out as a blisteringly red-hot example of the market’s current appetite for vintage SUVs and 4x4s, it’s most certainly the first-generation Ford Bronco. This boxy brute is all about rugged utility and durability, introduced as a competitor to the compact International Scout and Jeep CJ-5 SUVs. From the get-go the Bronco earned itself a loyal following, renowned for its capability on dirt trails and snowy roads alike. Completely analog controls, boxy look, bare-bones interior, and 289- or 302-cubic-inch V-8 engine make it a perfect foil for modern trends in. As first-gen Broncos boom in popularity, restomods are becoming popular and later Broncos are coming up to fill in the gaps where people are getting priced out of the first-gen market. Despite the final iteration going out of production in 1996, the current SUV craze is showing that the Bronco name still has a ton of equity, and Ford plans to introduce a new Bronco in 2020.

Buick actually makes a Regal today, but it’s nothing like the car that made performance junkies twitch with excitement in the 1980s. For the better part of a decade, starting with the Regal Sport Coupe for 1978, Buick was hard at work spicing up the Regal into various performance variants in accordance with the brand’s success in NASCAR. The tinkering proved fruitful, and when the quarter-mile-devouring Grand National arrived in 1984, it made the Regal a full-blown sensation. By 1986 the Grand National made 235 hp and had an available sport suspension package to boot. Other boosted G-bodies, like the Regal turbo-T, offered similar performance, but to this day, when people think of what car Darth Vader would drive, it’s a black Grand National. The holy grail arrived in the form of the GNX—a Garrett-boosted hot-rod powerhouse developed with the help of ASC/McLaren. Buick claimed 276 hp for the GNX, but that figure was widely considered to be underrated.

MILLENNIALS

(1) 1967–72 Chevy C10 Pickup  vs 2004–06 Pontiac GTO

Vintage pickups are becoming more desirable than ever, and C10 trucks are about as simple, attractive, reliable, and easy to drive as it gets. In 1967, Chevy released its second-generation C/K pickup, and the trucks made a huge leap from being purely work vehicles to more everyday comfort by including a lot of the convenience features GM previously afforded only to family sedans. Looking at the tech- and comfort-focused, do-it-all trucks of today that Americans positively adore, it’s easy to see the so-called “Action Line” C10 as the originator of these values. There are endless variations, options, drivetrains, and colors for the second-gen C10, which sold more than 290,000 units every year of production. That means you can find the perfect Chevy truck for your tastes.

Just remember—cars don’t have to be old to be collectible. People might think classic muscle when they hear “GTO”, but among Millennials, there are plenty of horsepower fanatics who think of the thunder from Down Under—the 2004–06 Pontiac GTO. Built in Australia and based on the rear-drive, Corvette LS1 V-8-powered Holden Monaro, the reborn GTO was the brainchild of GM President Bob Lutz. “Maximum” Bob got it done, although switching the Aussie car to left-hand drive and making it pass safety regulations too so long that the GTO’s stateside arrival was long overdue. And although it didn’t look like much, the 350-hp 2004 GTO was a monster, and its independent rear suspension meant it could do a lot more than just go in a straight line. Today, people especially prize the six-speed 6.0-liter LS2 cars that launched in 2005 with 400 hp and bigger brakes. Modern GTOs were niche cars that didn’t sell as well as GM hoped, due largely to the high $34,000 base sticker price and lackluster styling. These days, the coupe is an excellent performance bargain and one of the meanest sleepers on the street.

(2) 1989–94 Nissan R32 Skyline GT-R vs (3) 1984–93 BMW 3 Series (E30)

Sixteen years passed between the last “Hakosuka” Nissan Skyline GT-R and its successor, the R32. Like in the original GT-R, Nissan kept a straight-six under the hood, but the performance beast that became known as Godzilla packed twin turbos for its 2.6-liter twin-cam motor, pumping out north of 300 hp (although Nissan officially rated it 276 hp). What really made the R32 special, however, was its advanced electronically-controlled all-wheel drive, four-wheel steering, and multi-link independent rear suspension. It was a car bred for mountain roads and racing circuits alike, and the GT-R was an indomitable force in Touring Car series. For years it was impossible to get an R32 legally in the U.S., but since 2014 there’s been an explosion of cars arriving stateside as 25-year-old models exempt from most importation rules. Now, the people who as kids worshipped the GT-R as forbidden fruit, only attainable in Gran Turismo, can drive the real thing.

A successor to BMW’s 2002 sport sedan, the E30-generation 3 Series is the car that ingrained BMW in the American market, when the brand really took hold in the 1980s and got its reputation as a “yuppie car.” The yuppies had good taste though, because the E30’s fantastic chassis, strong powertrains, and timeless styling remain benchmarks for a lot of BMW fans today. Worldwide BMW sold more than 2 million units of the E30 3 Series, spanning wagon, coupe, sedan, and convertible body styles. Performance models like the six-cylinder 325is and the all-wheel-drive 325iX remain desirable for enthusiasts, especially now that the M3 is a blue-chip collector car out of reach for most people. The M3 debuted with the E30 generation, homologated for racing, and its on-track dominance is the foundation of the BMW M brand we know today.