Never* had a fun car, just never had the time or money (or enough of both at the same time) to go beyond something sensible. Even my motorcycle (an ancient 250 Rebel) is about as boring as it gets. Staring down 40 (a bit over a year to that), so the mid-life crisis might hit hard in the next couple years.

The Model T I can at least sort of see - it wasn’t popular because it was good, it was popular because it was common and cheap, more or less from the start (absolutely makes it important and influential though). Furthermore, the Model T was wildly outdated by the time it was discontinued, so not good *by the standards…

No smoking toddlers? THANKS OBAMA

Take your pick of British roadster - for a country with often middling, cool weather, they built a lot of cars meant to be driven through winding country roads with no roof, which sounds exactly on mission for an autumn drive.

As a bonus, the MGB could even be had with an interior colour called Autumn Leaf. I got to…

Isn’t it (left to right) Citroen SM, 80's Maserati Quattroporte, Maserati Gran Turismo, late BMW 2002, today’s XJS?

It’s a product of the 70's. Of course it needed two ashtrays. The better question is why the back seats, however small, did not also get ashtrays (or even the rear parcel shelf on the earlier 2-seat XJ-S convertibles).

I haven’t looked into it, but I thought a lot of the problems were early teething issues (after all, the Slant 6, LA V8, and 727 Torqueflite were all fundamentally solid powertrain bits) that got rectified later in production (but don’t quote me on that).

Late 70's A-bodies (Olds Cutlass and the like). I also had a college professor who worked for GM at the time, and ~30 years later was still ranting about the idiocy of making a hatchback shaped car that wasn’t a hatchback (I believe the window thing factored into his rants as well).

My experience with Chevettes is with them as 20yo beaters, but even in the rust belt, they’d take a bunch of negligence, abuse, and the absolute bare minimum of maintenance. I’m not sure exactly how much mileage was on the fleet of pizza delivery cars I drove, but they were all past the ~250k kms where the odometer…

I feel like to reach the standard of worst, it’s got to simultaneously be an unpleasant car to drive, and horrendously unreliable. While the Mustang II is by no means a great car, it’s mostly considered bad because it’s wildly different from a ‘70 Boss 429, but it made sense at the time.

The first thing that comes to…

Shelby Dodge Lancer

The 6 is dead in North America, but it got the turbo engine towards the end of its life. Quick, but they were aiming more for luxury with that one.

I’ll go one further - every single Mazda. They already want to be a budget alternative to the Germans, who do M/AMG/RS versions of just about every car they build. I’m not saying I’d have bought a Mazdaspeed CX-5 (because I’m cheap), but I’d have lusted after it stronger than the regular turbo I wasn’t willing to…

Make it a GMC Savana and get Mr. T on the phone ASAP.

Wait, sell a car? You can do that? Basically everything I’ve ever owned has been so worthless by the time I’m done with it it’s totalled, scrapped, or donated (I did trade my Mazda2 in, I asked for the BlackBook number, I got it with no protest).

My father-in-law has a new Silverado (for towing a travel trailer), and I think he likes it fine, but thinks it’s a bit stupid compared to the Nissan Frontier for loading stuff in the bed (and I think if it were feasible, he’d rather just have one of the Nissan Hardbodies he had in the 90's back).

My kid likes motorcycles too, and will sometimes waive them out of excitement. It got him a waive back a couple weeks ago while we were out on our bicycles, and I instinctually did the two finger waive. From my bicycle. Because I'm an enormous dork.

I learned to drive in a Sundance. It was absolutely a boring car, but my parents must’ve lucked out, because they got a good one (that, and it was a ‘93, later in production). In 10 years and 120k, we had zero issues, and it had plenty of life left in it (something we couldn’t say about the Pontiac Sunbird it…

Eh, ìt was pretty widely acknowledged to have gained weight from the original target moreso than it ended up with less engine than intended (although they did plan on a turbo option if they hadn’t gone defunct).

I’m only a few years older than you, it’s a franchise that was still releasing content in our lifetime, it’s not like it’s people getting excited about a reproduction of the space capsule that got launched into the moon face in that silent film. Hell, I’ve still got the BTTF2 Micro Machine set (with the DeLorean, Hill…