1957 Ford Thunderbird
A true classic car, the T-bird is usually the first thing on my mind when I think "dream car". While I'm not usually into convertibles, there's an inherent charm and machismo to it that really catches my attention. And while not unique to the Thunderbird, the engine has the BEST purr. I could listen to it all day.
1986 Ford Ranger
I LOVE THIS TRUCK. I used it for work many years ago, and out of all of our work vehicles, this one was the most reliable and fun to drive. It had just the right amount of bounce, and still kept GREAT speeds even when carrying heavy machinery in the bed.
1957 Chevy Bel-Air
My dad actually owns one of these, and it's been a staple of my life since before I was ten. Plus, the trim of the '57 is SO slick. Unfortunately it has a very poor safety rating, but you'll probably only drive this occasionally for car shows and the like. While I can't see myself buying one for my own sake, it'll always have a special place in my heart thanks to my dad.
2003 Audi A4 Quattro
My first (and current) car. I honestly wouldn't recommend it unless all you care about is speed and you find one with the V6 turbo trim. I will say, it has lasted MUCH longer than it was supposed to and still runs fast and (mostly) smooth. I still get compliments on it, and it's fun being able to outspeed assholes out on the road.