25. PONTIAC FIREBIRD TRANS AM
It was the dream car for the generation of American men who came of age in the 1970s—the ultimate expression of masculinity, like driving a fist down the road. When the Trans Am debuted in 1969, it came in one color: cameo white with blue accents. Price: $3,887. Engine: a Ram-Air 400-cubic-inch V8. Pontiac made the Trans Am until 2002, but its ultimate expression was the 1977 TA Burt Reynolds drove in Smokey and the Bandit. Worldwide Auctioneers sold Reynolds’s personal black Bandit mobile in 2011 for $57,750.
24. BMW 2002
The late David E. Davis Jr. launched this car’s (and BMW’s) fortunes in North America with his rousing 1968 Car and Driver article headlined turn your hymnals to 2002. This Bimmer (1968–1972) could outcorner the era’s British roadsters, with four aboard and Blaupunkt blasting. Early cars are the best (go for a fuel-injected 2002tii), around $20K today.
23. CHEVROLET BEL AIR
The 1957 Chevy is an American icon—a stylish ragtop with frenched headlights, pert fins and an attitude that says “Cruising or racing, I’ve got you beat.” With its panoramic wraparound windshield, gold-anodized side trim and proud V8 badges, the Bel Air was the desirable ride in the Dinah Shore days. At $113K for a top example today, it’s still “the Hot One.”
22. VW BEETLE
The Beetle has dubious beginnings. When Adolf Hitler took power in 1933, he turned a nation ravaged by the Depression into an economic juggernaut by empowering Germany’s auto industry. The Volkswagen (“people’s car”), brought to life by lead engineer Ferdinand Porsche, was part of Hitler’s plan. Had he lived, he would have eaten his rug on seeing the car appropriated by peace-loving hippies in the 1960s. The Bug to have today? An original from the first year of production (1946), notable for its split rear window. Expect to drop about $37.5K.
21. MAZDA MIATA
The best-selling two-seat sports car of all time, the Miata (or MX-5) was unveiled in 1989. It was an affordable, lightweight Japanese sports car inspired by the great 1960s British roadsters (the Lotus Elan in particular). Today the Spec Miata is the best entry-level SCCA competition car money can buy. Pick up a 1990 convertible for $7K and go racing.
20. PONTIAC GTO
Okay, so its actual name is Tempest LeMans GTO. Bypassing a General Motors edict on engine displacement in midsize cars (330 cid was tops), Pontiac’s engineers stuck a 389 cid V8 into a 1964 Tempest, and voilà—the muscle car was born. Some say the GTO is still the greatest muscle car of them all. A 1964 Tri-Power (three carb) today will run you a mere $71.5K.
19. CHRYSLER 300
Built to battle the new Corvette and Thunderbird, Chrysler’s first 300 (the C-300) was the fastest American production car of its time (1955). The race-proven hemi V8 could power this baby over 130 mph, and bodywise she was a stunner. Only 1,725 C-300s were built. More powerful Chrysler “letter cars” followed, but the 1955 is the purest and the best—about $78.2K today.
18. DATSUN/NISSAN Z
The “Z” blazed a trail for Japanese autos in America when it appeared in 1969. The original 240Z had a raked Ferrari-like nose, plenty of agility and a price ($3,500) within reach of the masses. The Z continues to blaze; the 390, the seventh iteration, is rumored to debut next year. But the simple, elegant lines of the original 240 still delight. Expect to drop about $24K.
17. FERRARI 458 ITALIA
A modern Classic, the 458 is the current mid-engine rocket in Ferrari’s lineup, a singular sports car that’s an amalgam of all the technology amassed by the most exotic of motoring companies in its 65 years of production and racing. Cornering in this car, with its 562-horsepower V8 screaming in your ears, makes you feel superhuman. The Pininfarina-designed body is as luxe and Italian as can be. Like a gorgeous model, however, the Italia is a tease. Only the superrich get their hands on this $230K supercar.
16. CHEVROLET CAMARO
Unveiled as A 1967 model by GM chief Pete Estes (who called it “a four-passenger package of excitement”) on June 29, 1966, Chevy’s Camaro was created for one reason: to topple Ford’s fast-selling Mustang. The pony-car wars have been with us ever since. Our pick of the Camaro litter is the first-year 1967 Z28 with a 302 V8 (602 were made), built for customers to race in the Trans Am series. The original sticker was $3,226. Today it’ll cost you about $67K.