If I could have any car on this list – I mean, BOOM – my car is suddenly gone, and this is parked in its place – I wouldn’t be mad. (Youtube links)

80s Suzuki Samurai
These are cool because they have the Jeep CJ look without the implication that you’re “in the club,” or whatever the bizarre camaraderie is that comes with driving a Jeep. It’s small so you can park it anywhere, has a removable soft top for the summer / beach, and is probably very economical with gas. My main concern with this vehicle is that it has very low horsepower, so despite its light frame being able to conquer off-road feats at < 5 mph, I fear it doesn’t have the juice to merge on the expressway. I bet going 65 mph, the transmission is spinning at 4000 rpm or more. Very loud and uncomfortable. The left lane is off-limits. In a best case scenario, people are honking at you thinking you’re taking your time while you actually have the pedal to the floor. That’s no fun, so I will probably never own this vehicle.

80s Chevy Blazer
This is a short wheelbase, full sized truck with a removable hard top over the second row of seats. I feel like this is the greatest vehicle you can show up to the beach in, because it has great presence, comes in basic, purposeful colors, and again, no top over the rear passengers. Very beachy! The drawback with the Blazer is its short wheel base – it probably rides poorly over bumps – also, it probably does < 10 mpg with its fuel. A true classic and a vehicle I would like to own some day.

90s Toyota Supra
This coupe looks amazing and has a legendary twin turbo V6 engine. It is probably so much fun to put the windows down and the sunroof back, and carve around some back roads at night with the heat on. The reason I will never own this car is because they have gotten too valuable. Growing up (2003-10,) I would see these cars for around $5000 because they were simply “old.” Now, they are “classic,” and as such, have gotten over valued. I would consider driving one of these if I could find one for a fair price.

90s BMW 540i
Of all the BMWs throughout the years, I have always been moved by the strong simplicity of the 5, of the era just before it got fancy. Yes, a new 5 would be nice, but there’s something about this particular period that really shows you are an enthusiast (not just someone with money.) 3s and Zs are too small… Ms and 7s are too showy… SUVs are too mommy. The reason I will never own a 1999 540i is because of their exorbitant maintenance costs.

60s Oldsmobile Cutlass
Of all the cars I have ever owned, my favorite was a 1994 Cutlass convertible – Torch red with black interior and top. I refinished the mag wheels in a gun metal color. It looked awesome, and was fast (3.4L DOHC engine.) It had very nice manners, too – with the top up, you could be riding quiet and smooth, doing about two grand going 65-75 mph. Nice 16″ mags with rather fat 225-sidewall tires. The steering wheel was covered in buttons so you could operate the heat/AC and radio with it. I don’t think I would ever buy a car twice, but the mid-60s Cutlass has a very nice look – I would like one with a small V8 in the same color combo, as an homage to my ’94. Just a simple, plain, true classic car.

50s Chevy Del Ray
Chevy had, like, seventeen types of “full size sedan” back in the day. The two doors, the four door, with post doors, without, the convertible, the wagon. The Biscayne, the Bel Air, the Impala. The Del Ray was the bottom of the heap, the two-door post-door style sedan bereft of any chrome, with crank windows and a delete plate where the AM radio would have been. Can you imagine not springing for the AM radio option? A ’58 or ’59 Del Ray in triple black is, I think, the coolest looking car of the 20th century. So low key, so quietly demanding in appearance. Cadillacs were nicer, but didn’t age as well. I would like a “sleeper” resto-mod example, looking factory but with a radio, moved by a 350 Crate engine, stopped with disc brakes.

90s Nissan Truck
I don’t know if there really was a model name for this “Truck” – It’s called “Hardbody” or “D21” – I think it was a leftover Datsun. A great investment – I could imagine getting one and spending $5000 on it over five years. ($3000 for the truck, $2000 on whatever it needs.) I cannot say that about any other vehicle on this list. They stopped making this truck for the US market in the early 90s, but kept on manufacturing it (unchanged!) through 2015 for Mexico. It must be a headache to import, but I would love to score a well maintained 2012-15 there and drive it home.

90s Chevrolet Impala
These are overvalued. You cannot find one in good shape for under $15,000. I think it’s silly – It’s only a Caprice with a trim package and nicer engine / wheels. You would be hard pressed to find a Caprice of that era in any condition for over $10k. But it has a sort of legendary status for enthusiasts, and so that is what you’re paying for. Me, I’m just a fan of V8 rear wheel drive sedans. This is one of the last of those, so if I could score a black or maroon example I’d enjoy it.

90s Toyota Corolla
Like the Nissan Hardbody, this car’s reputation for longevity and low maintenance cost has captured my interest for years. I really like some of the color combos they came in, like dark teal with tan interior. Just a plain, unassuming car that I would appreciate, that no one else would look twice at. I wish they did a 2-door or hatch like the 70s Corollas. These are only available as sedans.

2022 Truck
Ford, Chevy, Toyota, whatever – What’s the difference? A half-ton, 4WD, 8′ box – I’d prefer a regular cab, just so I could maintain some image of utility over posturing – Trucks are trucks, for better or for worse – It would be nice to have something brand new, but if I could have a 2022 anything, it would probably be a truck.
I can’t stand the numb feeling of front wheel drive, the empty promises of “infotainment” and “luxury,” and all these damned computers and sensors stopping me from maintenance and DIY customization. Cars used to be so much fun. What happened?
Leon