I've mostly owned shitty cars, so they all broke down. The quick version:
1st car, '60s Volvo- Bought for 1/8th of weed + $200. Started burning and leaking oil like you wouldn't believe, couldn't make it up to Snoqualmie Falls it started smoking so much. Turned around, hobbled home. Sold to an anarchist for $200 in coin who preceded to not register it and rack up thousands in tickets, which they mailed to me. Total nightmare for years to clear off my record.
2nd car, '70s Hornet, green to boot! - Bought for $300 and ran great for a year. Water pump died on a road trip by Portland. While waiting for a tow truck, my wife's cousin happened to drive by. He and I grabbed his tools at his house, a water pump at an auto parts store, and replaced it and we were on the road again in less than 2 hours. Awesome! Sold for $200 to a girl in Fremont that wanted me to discount the price in exchange for "a massage". Didn't take her up on it. She promptly painted a witch riding a broomstick on the side of it, I saw her driving it later.
3rd car, '80s Escort Wagon, bought for $600 from the mom of my main 10 Things artist. Worked excellent for 2 years until it caught on fire on a road drip on I-5, right after that conservative uncle sam sign! Had it towed to my friend's field where we were having a big camping weekend. Later sold it to a local meth head for $1 just to get it out of my friend's field, only after sending him the title and keys, he never picked it up. Turns out he had gotten locked up. It remained in the field for 5 years, and we had a yearly camping trip there and would look at it and I'd feel sorry about abandoning it on my friend. Eventually a metal scrap guy picked it up for free.
4th car, Ford Ranger pick up, my first real car, only 50,000 miles on it. Was great for about 5 years, until the transmission went out on a road trip on a gravel Forest Service road in the Gifford Pinchot. Managed to hitch a ride with my girl and dog to the next town 45 miles away where I found Amy's cousin drinking from a bottle of Jack and convinced him to go back up the mountain and tow it down with his rig. Replaced the transmission in Hood River, it started to go out after another 20,000 miles, I hate Fords! Sold cheap.
5th car, current, Toyota Tacoma truck. I've done nothing to it besides change the air filter and oil and get new tires. Totally rock solid for 7 years hauling shitloads of arcade games and pinball machines, but starting to get up there in miles now and whine a little. I'm thinking I need to buy a new truck soon.