Over the years I have owned a lot of classic cars, but enjoying the hobby doesn't mean you need at a six-figure budget and a weekend at the auto auctions. I searched several popular sites, Craigslist, eBay Motors, and Hemmings to find what are some of the coolest classics you can get for under $5,000 and start enjoying them right away.
The cars had to be common enough to come up for sale in different parts of the country, the cars had to be running and driving, and they had to be listed at $5,500 or less (I figured you could haggle that extra $500 away).
(* = Cars I have owned personally)
With five body styles including a coupe, convertible, wagon, pickup, and sedan the Falcon is one of the most versatile cars Ford ever produced and would go on to be the platform that the Ford Mustang would be based on. The majority of the Falcons were produced with inline 6-cylinder engines, however, V8 models were offered and are a popular engine swap. If you are looking for a Falcon be sure to also search for its sister car the Mercury Comet.
Chevrolet's answer to the influx of compact import cars was the Chevrolet Corvair, with an air-cooled, flat six engine, the Corvair was more like a VW than a Falcon, but like the Ford Falcon the Corvair came in a number of body styles coupe, convertible, sedan, station wagon, passenger van, commercial van, and a pickup truck. The Corvair is an American classic with a European feel, while the first generation was deemed "Unsafe at Any Speed" by Ralph Nadar, adding a front swaybar addresses the handling issues.
1961-1980 MG Midget*
A car that changed with the times while still keeping is charm the MG Midget was one of the most popular import cars brought to the US. Based on the Austin Healey Sprite the cars are often referred to collectively as Spridgets. With two seats, a manual transmission, and little more the Midget is a pure sports car. Early models are more desirable, they lack the higher ride height, safety bumpers, and smog equipment choked engines of the later cars. If you are not a fan of convertibles, fiberglass hardtops were very common and can be found inexpensively.
The fifth generation of America's best selling truck the F-100, F-250, and F-350 was redesigned for 1967 but still offered an assortment of six and eight-cylinder engines. Offered in a regular cab body style with a crew-cab for fleet customers, the F-Series is a practical classic you can work on, take to a car show, and use for those occional trips to the hardware store.
With classic import sports cars like the Datsun 240Z creeping up in value alternative cars like the GT6 are sure to rise in value as well. The Michelotti fastback design for the Spitfire roadster proved to be more aerodynamic, but the extra weight meant the standard Spitfire 4 cylinder needed to be upgraded, a 2-liter OHV engine from the Vitesse sedan was fitted to the smaller fastback and the GT6 was born. When looking for a GT6 69-70 model years (Mark II) have the classic styling of the MKI model but improved handling and other improvements.
1938-2003 Volkswagen Beetle
A version of the Volkswagen Type 1 was manufactured somewhere in the world for an incomparable 65 years, resulting in over 21-million being produced globally. This and the fact that parts are inexpensive and easy to find make the Beetle one of the cheapest classics you can buy. The Beetle is one of the most iconic and important cars in automotive history. As the car was constantly being improved you get a very different driving experience in a 1950 Beetle compared to a car built in 1970, so depending on how much "charm" you are wanting in your classic buying a later model car might be best.
If you want something really different the Saab Sonett fits the bill, very early models had 2 stroke engines, but bu 1967 a 1,500cc Ford V4 engine was sourced making volume production possible. The V4 engine wasn't the only thing that made the Sonett unique, it also featured a freewheeling clutch that would automatically disengage when you took your foot off the gas and it came standard with a roll bar, three-point seatbelts, and other safety innovations not seen on small sports cars of the day. The Sonett II and III have their own unique looks, but both are two-door fastbacks that raced in the SCCA, and both had the same Ford power plants. While Sonetts are almost never expensive they are rare, find the best on you can as spare parts can be hard to come by.
The 1961 Thunderbird was sporty, classy, and really captured the jet-age styling that made the early 60's so cool. Offered in Coupe and Convertible a decent driving coupe can be had for under $5,000 if you hunt around. Try to get a car with all of it's trim, because there is a lot of it, and many parts are no longer in production, you might find a deal on a driving 62 T-Bird for $2,500, but you will spend thousands on finding and reconditioning all of the chrome.
The Dart and its sister car, the Plymouth Valiant, were all new for 1967 and offered a wide range of engines from a standard 170ci Slant-6 engine all the way up to 440ci Hemi (in 1968). The Dart was like many cars from the 1960's a compact economy car with muscle car options. The Swinger name was given to the two-door hardtop models and would be the car to look for. Dodge offered several special editions and packages on the Dart so don't be surprised if you find a car with a metal sunroof or a fold-down back seat.
The Alfa Romeo Spider was a holdover from the 1960's and while the early cars are very valuable, the 1982-1989 series three cars are a great value. The 3rd generation cars came with 2.0 liter Bosch fuel-injected engines and were offered in a few variations the most desirable being the Quadrifoglio Verde model. Hardtops were optional and in 1990-1994 an automatic transmission was offered.
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