I miss driving a hooptie. There, I said it. The admission is kind of freeing, like admitting you have a problem and are on the first step of a recovery program. I don't need to drive a hooptie--I have a very nice, two year old Ford Fusion--but it lacks the humor and drama of driving an old car that gets you from Point A to B.
There's also a peace of mind that comes from owning a hooptie. You can park it anywhere without worrying about it getting scratched or dinged. If the only spot in the parking lot is next to a hulking Escalade that's parked over the line, you can pull right in next to that badboy. If it gets stolen, you're out maybe a tank of gas and some old Aerosmith cassettes.
In twenty-five years of car ownership, I've owned a long line of hoopties--from a 1973 Volkswagen Thing, 1982 Toyota Celica, and a 1990 Buick Century to a 1997 Infiniti and a 1997 Olds Cutlass. All of those cars had issues, but they got me where I needed to go, and they cost less to own per month than my current car payment.
There is also an entertainment factor in owning a hooptie. If you're single, it will probably cost you a lot of second date unless you're seeing someone who's equally cheap and has an odd sense of humor. It provides comic relief in addition to the relief from monthly car payments.
But if you're a car person, or just like an underdog, there's just something lovable about an old beat up car that makes you want to root for it.