Since you didn’t mention reliability, what about a first-gen Audi S5 with a nice big V8 (the same 4.2 FSI from the RS4 before they switched to a boring supercharged V6 in 2013). There are quite a few examples in your price range with under 100k miles. They are a bit heavy but they make a nice noise, are super composed …

Hasn’t “Mustang” been the correct answer to this question since time immemorial? With that said, if you only have regular car money to spend, maybe buying a secondary “fun” car isn’t a super good decision for you.

This GTO is at a dealer in Houston.  Miles are reasonable.  Price is comfortably within budget.  I’m not a fan of the custom blue bits on the interior, though.

There’s always one!

Challenger is your answer. I’ve had a V8 of one sort or another almost all my driving life (40 years). I own a late model Challenger now, purely as the sort of car that our reader is asking for, and nothing before has ever made me smile so consistently as this car. It does everything. It does it well. And mostly, it’s…

Find an 06 GTO. 

I’d get a Vette. Maybe consider a Mustang or Camaro if the under $20k Vette market is looking rough.

Well, how about Mercedes.... it is basically *better* American Muscle.

Joe Doesn’t want: A truck or SUV

Miata is always the answer...just need to LS swap it.

C5 is the correct answer. Easy as dirt to maintain as well.

Ramcharger was right there too.

We do not discuss it with outsiders.

DeLorean. The powertrain is forgettable and there is historical precedent of electrifying it with a plutonium reactor.

This is an easy one! The Delorean DMC-12. Though it has been done before by DMC in Humble, Texas, the Delorean will always be a fantastic EV candidate due to the once, “futuristic” appeal of this car, the Back to the Future correlation and the fact that the OEM PRV V6 was a colossal pile of crap. 

Teslas. 

The original Delorean can only be improved by swapping out its engine. Electrifying it would be a good stopgap until we get to Mr. Fusion.

That’s the thing - I, nor most people who drive the things, am never going to have to haul a full trailer of sod around - if this is something you need to do on the regular, you do you. But my Land Rover Disco could haul that trailer just fine, while also having the back of it full of stuff I don’t want to get stolen…

Mostly because everyone you know is asking to borrow it. 

I doubt it. I hate driving the things. I don’t see the point. If I want to go off-road, I want something that is actually good off-road like a Jeep or a shorter SUV (I own a Land Rover Discovery for that sort of thing). Pickups are too hard to load and unload compared to a utility trailer, can’t haul anywhere near as…