Return on investment can be measured in many ways. In cars, though, it's almost always twofold: fun behind the wheel and financial prudence (a.k.a., not losing your shirt). The first is easy, especially if you've got a real budget. The second, however, is rare. Getting both in one car is like finding a unicorn in Detroit.
But it can be done.
We found 10 cars (OK, there are a few trucks) that are decidedly cool, hold their value and aren't likely to depreciate while you enjoy them. Heck, we'd even bet you could make money on most.
As always, there are exceptions. Maintenance costs are the big one and it's hard to pin down which car might do the least damage to your wallet in the long run. A good pre-purchase inspection with a reputable mechanic will go a long way in making sure you buy the right car. So will some real research. All of these cars are supported by a library of Web-based knowledge, so there's no excuse. And even though there are no guarantees, there are some pretty solid bets.
So here they are.
1991 Acura NSX
Why: It's been nearly a decade since the last new NSX rolled off the assembly line and early models are now starting to demand higher prices on the used market. The first year (1991) can be found for just over $20,000 if mileage isn't a concern, but any at- or sub-50,000-mile '91 NSX is going to start above $30,000. The 1991 NSX holds its own even among contemporary cars; its precise manual steering and snappy gearbox continue to offer supercar performance while it remains incredibly comfortable (docile, even) as an everyday driver.
With development involving Formula 1 icon Ayrton Senna and its "plucky upstart" status versus the Italian and German supercars of the day, the legend of the NSX grows every year. You'll be hard-pressed to pull up to a Cars and Coffee event in one without drawing a crowd of grinning admirers. As well-maintained early NSXs become rarer, their prices are on the rise: A thorough pre-purchase inspection will help mitigate repair costs of a car that only gets more special with age.
1988 BMW M5
Why: The first-generation M5 came to the U.S. in small numbers (around 1,200), but it made a big noise with enthusiasts and the press, beginning a legacy of "super sedans" that continues today. Each successive M5 vies for the Best Car in the World title, but it's the 1988 original that stands out as the greatest-ever melding of balanced, driver-focused performance and luxurious practicality. And let's be honest, there's no questioning the cool factor of a body that was penned in the late '60s.
Despite their rarity in the U.S., many original M5s are driven daily by outright fanatics. While everything else may fail, the 3.5-liter inline-6 engine tends to be rock solid even with high miles. Featuring individual throttle bodies, the U.S. car pumped out 256 horsepower. Surviving 1988 M5s are rare, but many can be found for less than $10,000 with high mileage and (too often) with questionable modifications. Be prepared to shell out upwards of $15,000 for a lower-mileage example with any kind of service record history, and make sure you know a good BMW specialist.
2010 Ford F-150 SVT Raptor
Why: Merely looking at the Ford SVT Raptor is a visceral experience. It looks as if it just drove out of the Baja 1000, which would be a mere amusement if it didn't actually deliver. But it does. Off-road, the Raptor can handle just about everything a sane driver will want. And it does it without sacrificing on-road comfort or handling.
The interior is as soft and welcoming as any American cruiser and the 6.2-liter V8 (make sure you get the 6.2-liter) cranks out 411 hp and 434 pound-feet of torque, and makes an unholy racket that will put a smile on your face every time you fire it up. Drop some coin on a low-mile Raptor now, or three times that amount in 20 years at some big auction in the desert: your call.
2005 Honda S2000
Why: Honda's beloved S2000 sports car is no longer in production, but its fandom continues. S2000s can be found throughout various model years at fair prices, but it's the post-2004 cars that are truly engaging. And if you want the best S2000, look for a 2005 model. Many fans decried the reduction of the original S2000's 9,000-rpm redline to 8,000 for the 2004 model year, but the shorter 1st through 4th gears along with the increase in usable torque at lower rpm makes the 2005 a more livable car. It simply offers more performance where most drivers actually use it.
With its forward-thinking digital instrument cluster, possibly the best six-speed manual transmission ever made and a naturally aspirated specific output only surpassed when Ferrari released the 458, the S2000 is one of the last great everyman sports cars. Plus, its reliability is exceptional, so feel free to fling a few extra bucks out for a lower-mileage example.
2007 Jeep Wrangler Unlimited
Cost: $17,000-$27,000 (X); $18,000-$33,000 (Sahara); $24,000-$39,000 (Rubicon)
Why: When the four-door 2007 Wrangler Unlimited made its debut, the naysayers came out in force: Four doors went against the ethos of the ultimate everyday off-roader. The stretched wheelbase made the Wrangler too big. It's less capable on difficult terrain. On and on they went.
But Jeep pulled it off.
The Wrangler Unlimited is not only a great off-roader worthy of the Wrangler name, but it's a unique SUV setup that can't be had with any other brand. On top of all that, the modern Wrangler is among the leaders in resale value: and somewhat surprisingly, nowhere is this more evident than with the 2007 Unlimited. It's difficult to find a sub-50,000-mile 2007 Wrangler Unlimited for less than $20,000. For a rough-and-ready SUV that can take you where you need to be with rear seats that fit actual humans, it's hard to argue with a 2007 Jeep Wrangler Unlimited.
1997 Land Rover Defender 90
Why: The 182 hp from the Defender's 3.9-liter V8 sounds underpowered today, but when mated to the tried-and-true all-wheel-drive setup of the Range Rover it proves more than enough to do what the Defender was built to do: go anywhere.
The 1997 model-year Defender 90 was the last to be brought to the U.S. market. The niche appeal of its old-school off-roader aesthetic combined with ever-shrinking numbers of well-maintained cars conspires to keep prices exceptionally high. When you see a Defender in person it's easy to understand why they're so coveted: the square-ish, bulky body mated to big, mud-stomping tires tickles just about all of the basic instincts of off-roaders. Built to get you wherever you need to go in all conditions, the Defender 90's high cost of ownership is outweighed by its cool factor, scarcity and raw capability.
1992-1994 Mercedes-Benz 500E/E500
Why: In the early 1990s as BMW's M5 established itself as the performance sedan of choice, Mercedes-Benz needed a competitor. W124 E-Class chassis (upgraded with big brakes and the 5.0-liter V8 from the high-end 500SL) were shipped to Porsche's Zuffenhausen plant for assembly.
Only 1,500 were brought to the U.S. during a three-year production run (for its last year in 1994 it was re-designated the E500) so it's becoming harder to find well-maintained low-mileage examples. Diligent searching will pay off with a "sleeper" classic, featuring the grunt of the 5.0-liter V8's 322 hp, a fascinating history and the quirky charm that comes with being "the other guy." Overlooked even by many Mercedes fans, the 500E is a cool divergent footnote in automotive history that also happens to go really fast.
1995 Porsche 911 (993)
Why: For many Porsche devotees, the 993-era 911 represents the pinnacle of what a "real" 911 should be: air-cooled, small and focused. Its replacement — the water-cooled, daily-driver-focused 996 — was bigger and heavier. The culmination of more than 30 years of innovation and refinement, the 993 offers classic 911 handling while its air-cooled flat-6 makes all the right noises.
As a benchmark 911 model, the 993 retains its value on the used market. As the years go by, more 993 owners either decide they can't part with their treasures or they have "off-road incidents," so expect more scarcity of selection and higher premiums to buy into the club.
2011 Porsche Boxster Spyder
Why: A fitting last hurrah for the 987-era Boxster, the Spyder edition was produced as a 2011 and 2012 model before the introduction of the current-generation 981. It is nearly 180 pounds lighter than the 987 Boxster S and brings 10 additional horses to the table (320 in all). The Spyder was (and some still say is) the hot roadster to own.
Sitting 1 inch lower than the regular Boxster and with a stiffened suspension, the Spyder enhanced the already excellent driving characteristics of the Boxster to miraculous levels. The 2011 Boxster Spyder entered the market as a production model, so for now at least it's not terribly difficult to find a used one with low mileage and a clean maintenance history: but it is expensive. Buying and babying one of these now may prove to be a sound investment as they become rarer in the future. In any case, it'll be a fun investment.
2004 Subaru Impreza WRX STI
Why: The first-year of Subaru's rally-inspired WRX STI stuffs 300 hp and an impressive all-wheel-drive system into the restrained and practical Impreza sedan. Few cars yield the STI's combination of high performance and four-door utility.
The inconsistent availability of Subarus in various U.S. markets means that used pricing is all over the place, but look to spend at or near $20,000 for an example with fewer than 100,000 miles on the clock. Lower-mileage 2004 examples can climb into the mid-$20,000 range: impressive considering the $31,525 MSRP of a new 2004 STI. The 2004 STI did more than establish Subaru with American enthusiasts; it created an entirely new segment of performance car made to handle alternative roads and weather. And families fit, too.
Grab a 2004 STI now before it is officially deemed a modern classic.
Note: Not every car pictured is the exact year specified, but each does represent the correct generation.