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The $5,000 Challenge, from the ’60s to the ’00s edition

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Every generation of auto enthusiast has a decade that resonates with them, for better or for worse. While the cars of the 1970s may have been crippled by emission regulations and plagued by occasionally indifferent quality control, few would argue that they were more distinctive, style-wise, than contemporary automobiles. For someone who came of age in the 1990s, perhaps it’s the cars of the 1980s that are most appealing, and somewhere, someone is pining for the good old days of the aughties, the dawn of the 21st century.

This $5,000 Challenge (and yes, we’re adhering to that price CEILING this round) runs the gamut from the 1960s to the early 2000s. Some vehicles need restoration, while others need little more than a tank of gas, a thermos of coffee, two bags of beef jerky and a sense of adventure to enjoy. Which one, or which ones, do you find most appealing?

1966 Chevrolet C60 dump bed

1966 Chevrolet C60

How many times have you wished that you owned a dump truck? Not the full-on-industrial-size Mack, which is expensive to run and difficult to park at the shopping mall, but rather a more suburban-friendly model? This 1966 Chevrolet C60 dump bed may be the perfect weekend truck for the average homeowner. It’s big enough to haul dirt, gravel, bags of cement or a pair of racing motorcycles for weekend fun, yet small enough to fit in the driveway, if not in the garage. With a working dump bed, offloading the contents of a Costco run, or junior’s college apartment, is as simple as raising the 12-foot bed skyward. The asking price? $3,950.

1966 Chevrolet C60 1966 Chevrolet C60 1966 Chevrolet C60 1966 Chevrolet C60


1977 Chevrolet Monte Carlo

1977 Chevrolet Monte Carlo

In the 1970s and early 1980s, Monte Carlos were as common as cigarette burns on the vinyl upholstery at the local Waffle House. Now that they’ve all but disappeared from the American automotive landscape, we find ourselves thinking that they weren’t bad looking coupes, in a ‘70s kind of way. This one sports a few performance upgrades and a rebuilt engine, and the Keystone wheels give it period correct street cred. The asking price? $4,800.

1977 Chevrolet Monte Carlo 1977 Chevrolet Monte Carlo 1977 Chevrolet Monte Carlo 1977 Chevrolet Monte Carlo


1987 Porsche 924

1987 Porsche 924

Someone once said that there’s nothing more expensive than a cheap Porsche, and they were probably right. Approached from a different angle, this new-wave decade Autobahn-burner sits poised to offer its next owner an education in driving and in wrenching, and every education comes at a cost. Risk aside, we think this Porsche has great potential as a budget track day or autocross car, and as others have demonstrated, a small block Chevy can be tucked between the fenders if the 2.5-liter German four ever proves too finicky. The asking price? $3,000.

1987 Porsche 924 1987 Porsche 924 1987 Porsche 924 1987 Porsche 924


1993 Ford Mustang LX convertible

1993 Ford Mustang LX

Do you long for the days when a Fox body Mustang in good condition was affordable? For those willing to live without V-8 power, they still are. This drop-top example, from the limited pictures provided by the seller, appears to be in better-than-average condition, but beneath the hood it’s packing the humble 2.3-liter four mated to a four-speed automatic overdrive transmission. For those who travel at a relaxed pace, the 105 horsepower and 135 pound-feet of torque may be sufficient, but those wanting more can always drop in a 5.0-liter V-8 and five-speed manual. The asking price? $4,000.

1993 Ford Mustang LX 1993 Ford Mustang LX 1993 Ford Mustang LX


2005 Dodge Magnum R/T

2005 Dodge Magnum R/T

Those seeking a project car won’t find this late model Dodge Magnum R/T to be of interest, but those with a passion for road trips are probably already figuring a way to make space for this wagon in the garage. As someone who once piloted a Magnum SRT-8 on One Lap of America, I can tell you that these are fantastic cars for gulping down highway miles at supra-legal speeds. Killed off too soon, these surprisingly nimble wagons were, perhaps, the best thing to come out of the ill-fated Daimler-Chrysler marriage. If this example doesn’t sell soon, I’ll be tempted to snap it up myself, so please spare me the potential divorce. The asking price? $4,500.

2005 Dodge Magnum R/T 2005 Dodge Magnum R/T 2005 Dodge Magnum R/T