even though I own a 1973 matador, I have had nothing too terrible happen. there was a phantom electrical problem when starting. if you drove the car all the time it would be fine. if you let it sit a weekend sometimes you turn the key and nothing happens. I tried starting in neutral, replacing starter components, everything. then out of nowhere it would fire and drive like nothing happened.
the van my band uses to tour in full on burst into flames on the highway outside of ames, iowa. the fuel line burst near the carb, dumping fuel all over the exhaust manifold and making a bunch of fire. we got it put out thanks to a mysterious stranger and were able to get back on the road.
all of the electrical had to be rebuilt, and the distributer cap and wires were melted and every line and wire had to be replaced. the funniest was we had the van half unloaded before we thought to wake the guitar player up and get him out of the van. whoops!

a toss-up. i had a gold '79 olds cutlass supreme for a little while. the frame was cracked near the rear right wheel. it leaked coolant, but not so bad; i pretty much had to fill it up every few days. but the best feature of this car was the fact that every time it rained, water would come pouring into the passenger side floor. there was a puddle of standing water pretty much all the time. this was, i'm told, a result of the heater core crapping out somehow. which, oh yeah, also no heat.

the other car was totally different. it was an 80-something olds cutlass sierra. i bought it from an acquaintance of my dad's. we went to the guy's house, gave him $500 i think it was, signed the title, and hopped in the car to drive it home. it made it a couple/few blocks before the transmission seized up. after putting it in neutral and starting it back up, it was fine. a few blocks later, same thing. then it wouldn't restart, so we pushed it into a grocery store parking lot. apparently there's some thermo-sensing device associated with the trans that was malfunctioning, and it decided it was too hot and had to be shut down? that's what i was told anyways, apparently they sold it to someone else (gave me my money back, whew!) who just removed that thermostat or whatever it was, just pulled it out, and the car ran fine. so i don't know how much i really *owned* that car, but in terms of bad performance, that's the worst i've had, all ten minutes of it.

my '86 olds cutlass supreme is sitting in a parking lot about 2 miles from my house. paid $150 for it. drove great for the last two years. no major problems. three weeks ago, after two years of using my steering wheel as a high hat and snare, the whole steering column fell apart.
make a right turn, i shift to 1st and turn signal on to the right.
make a left turn, throws it into park and turns signal on to the left and cuts of engine somehow. but its okay! my insurance was about to go up anyways because of an accident i just had and my license was suspened because i didnt pay my ticket on time from the same accident.
oh yeah, that same accident caused me to get fired from my delivery job.
fun fun fun!

Just a few of the choice rides I have owned:

The Chevy Silverado that had mice.

The Dodge van with the dodgy solenoid. To start engine: Attach jumper cable to bundle of wires under the hood. Return to driver's seat with other end of jumper cables. Now, wiggle cables gently and rhythmically, as if cracking a whip on a team of frail ponies. Turn key until engine starts.

The Plymouth Fury with the bad flywheel. Turning the key, you'd usually get a horrible grinding sound. Then you had to pop the hood, lean on the alternator belt, and rotate the engine a few degrees. Then, you'd go back and turn the key again. Repeat as necessary.

The Chevy Celebrity with cancerous rust. My co-worker dubbed it "Lesions." The rear brakes would lock up with little provocation -- this was especially fun on snow or ice. Then the latch on the driver's side door failed. I used a screen door hasp and . . . velcro! . . . to keep it shut during use. Careful on those hard right turns!

I'm 26. I've had 12 cars. In 2000 I bought a new Mustang (still making payments), but prior to that i'd never had one newer than '87 I think.

One ran for about 6 hours and that was it. One NEVER ran (pulled the engine when I got it, and while the engine was in pieces on the garage floor that night, grandma decided for the first time in her life to "clean" the garage and threw away every bolt and small part. Those '68 strait 6 Ford Falcon parts are kinda hard to come by.) I wrecked one that I'm not counting. I wrecked a couple that I am counting. One could fit 5 freshman comfortably in the trunk. One could sleep 11 comfortably on the New Orleans waterfront for 3 days, (at least it would have been comfortable if one of the 11 hadn't peed all over the whole interior on the first night. Come to think of it, he wasn't one of the 11 at all, that jerk slept in a different car...)

But Anyway, my two favorites were:

Runner up:
'75 Ford F-250. 460 Ford (Wasn't Ford the 460? I think so.) On the back roads you could watch the gas gauge move. Granny Low. Had to take off in 2nd gear. Reverse was sort of at the discretion of the automobile. No floorboard in the driver side. The guy who bought it new used it to haul scrap metal for about 20 years. I think I got it from him in '95. When he got tired of the buff yellow paint job, he just got out the spray paint and solved the problem. But I guess he ran out, cause there were a couple different shades. And the inside of the bed was (per side from left to right) blue, white, and black (the bed was rust.) And eventually I hopped in the bed and noticed that the roof was still yellow. He probably had bad knees. I never did bother to put that air filter back on the carburetor. It was more fun to let it just keep catching on fire. One time my little brother poured a 44 ounce Dr. Pepper strait down the carburetor to put out the fire before it exploded in front of "Blimpie's." That floor board really sucked in the winter, and when it rained. But I reasoned that it made for an excellent escape hatch. Oh... and after a while I realized that it was unneccesary to continue giving it oil. It just made it smell worse, it was gone in a few hours anyway, and besides it didn't need it. That was just about the only car that still ran when I sold it.

Winner.
'73 (I think) AMC Gremlin. It was Red/Orange with yellow pinstripes. I never actually got this one on the road. I grew up on a farm, of sorts, and my dad got this for me and my little brother when I was 14 so I could learn how to drive. It was a Christmas present. All my other relatives new I was getting it, including one that worked at "Auto Shack" (remember when it was still auto shack?) He picked up every gaudy option you could possibly imagine for that thing for us (that totaled about 35 bucks). Doorjam protectors, 3 blade wipers (both neon green) and obviously dice, etc. More I can't remember anymore. Anyway, being the only 14 year old I knew with a car, I got pretty popular pretty quick, and we destroyed that thing. I was our source of fun for most of the summer, until I came out to take a drive one morning and discovered why my dad had warned me not to leave the windows down in the corral. Our horses ate car. They ate everything that was lime green. They ate the dash. They ate the radio. They ate the antenna. And they ate the seats. The seats were just a 3-6 inch layer of yellow foam all over the floorboards and the corral. Bare wires. Sick horses. At that point there was no reason to resist head on collisions with trees.

My friend Jim back in High school had an '81 Honda Civic Wagon that was the source of much entertainment. He was the bassist in my old band, so I was often present when these things happened.

He originally bought it from a friend of ours' dad for $21. The right front was wrecked a bit, but still drivable. It also had this huge bumper up front that stuck out about a foot. It was silver with some brown-rust coloration (BL).

About a week later, jim locked his keys in his car, so he threw a rock through one of the smaller rear windows. And the glass and rock stayed there for weeks, and the window was never replaced.

Then his exhaust pipe fell off inches away from the engine block, so you could literally hear the car from like a mile away in the country.

He also installed a crank onthe steering wheel and a reverse beeper like on the big trucks. But the beeper got wet or something and sounded like it had dying batteries, it was impossible not to fall over laughing when he backed up.

FInally, it its dying days, when jim was having to hit the engine block with a rubber sledgehammer to free up the carbourator (spelling?) in order to start, we were driving down the road, and the dashboard fell into our laps, and it was then that it was time to retire it. It had 207,000 miles, and as far as I know it's still sitting in his parents' yard.

OK, I gots to chime in on this one...

First car I ever owned... a 1980 Chevy Monza that I bought sometime in 1991 or so in Champaign, IL for like $500. At first, the car seemed like it ran fairly good. You had to laugh though at the flat rust-red paint with the white Starsky & Hutch stripe that run across one side up over the roof and back down the other side though...

This was my first and last experience with a 'stick', for a two reasons
(You can give me all that bull you want to about how automatics suck, but I simply don't' care)

#1) For some reason the damn clutch cable would break ALL the time... must have replaced 3 of those within a year or so... the last time the cable broke on me, the mechanic told me he flat-out could not put another one in because there was nothing left to attach it to (?) due to excessive rusting of the firewall or somesuch. I finally found another mechanic about 30-45 minutes south of Urbana who just welded a massive hunk of metal in there and fixed the cable up again. The drive out there involved my friend Ray driving behind me and every time I absolutely HAD to come to a full stop (red light or stop sign with opposing traffic) Ray would have to push my car with his until I could jam the fucker into gear again. That was a tedious drive.

#2) What truly cemented my negative opinion about the manual transmission though was the first time ever I was fortunate enough to be with a young lady who wanted to orally pleasure me while I drove. Well Jesus we were in the city and you just can't "maintain" when you have stoplights and stop signs every fucking block! It worked out OK for everyone in the long run, as I took my frustration out on her in a manner that she truly enjoyed once we got home, but still... I knew then and there that I would NEVER own a shitbeast 'stick' again. When your transmission choice gets in the way of your headjob... then you know your priorities are all fucked.

I hated this car so much that I literally gave it away. I was getting ready to move out of state that summer and a gas-station co-worker who never ever had 2 cents to her name expressed interest in it. I signed the title to her right then and there and said "Enjoy." She insisted on taking my new address and promised to send me "a little bit each paycheck" but I never got any $$$ from her (I already knew I wouldn't when I gave it to her) and I still really didn't care (I bask in the confidence that the karma of the clutch cable caught up to her) and this was back when even a hundred bucks or so would have meant a lot to me (DID I MENTION THAT THE CAR INTERFERED WITH ME GETTING BLOWN?) Yeah, I hated it that much.

Of course, the best part about posting this story is that I have now made the SpellCheck to "Learn" the words shitbeast and headjob.