I'm a huge fan of the "scruffy but nice 10 year old luxury car". They're affordable, well built, unique, and fun.
My daily driver is a '97 Lincoln Mark VIII that's been worked over into a moderate 1/4 mile drag car. The confluence of luxury and brutality is quite fun, and an interesting study in contrasts.
It's quite dynamic for a 2-ton luxury car, as well. Certainly the best domestic luxo-sport available until the recent Cadillac V-series came out. Also one of the few modern domestic luxury vehicles that can credibly compete with the imports, IMO.
I also have an older Triumph convertible that's more of a toy car. Right now it's taken apart and awaiting an engine swap, as the old British 4-cylinder that came with it is heavy, slow, and unreliable. But other than that it's great.