I would say Supra, no questions asked. Not just because I'm a Supra nut.
If I had a C5 Corvette, even a Z06, I would honestly get a strong "second-best" sort of feeling when I saw a C6 Z06 on the road, or even in pictures. It's sort of the feeling I had when I had my MK3 Supra. There isn't a generation of Corvettes or Supras that I didn't like (C4s are da bomb!), but for me, I gotta have the best, the latest and greatest, or I feel like I only got the second best.
Hope that makes sense without sounding too emo.