When I was 16 I bought a '77 300D. It was slow, but bearable.
It never left me stranded and put up with a 35 miles of commuting to school every day loaded with 5 kids.
I could afford the maintenance and fuel bills too.
It wasn't the coolest car around, but I never got pulled over in it either. When a kid in the parking lot hit me from behind, his car had over $1000 in damage, mine had a scratch.
Now I'm on my 3rd Benz.