I think the Chrysler Crossfire is cool. Very Art Deco lines. Might be budget-busting here. Maybe one with 10,00 miles on it.
I've always wanted a Jeep. Not so practical, but fun.
Don't know what the Prowlers are going for these days.
Something about the SSRs are cool.
That's all I have for American. If you cross an ocean in either direction, the list grows exponentially.