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I'm a C6 owner (almost bought a C5 last summer but I had just graduated and was a few thousand dollars short) but I can still appreciate the C5. The only thing that's dated about the C5 (besides the subpar interior) is the popup headlights since it was probably the only car to still have the popups in the new millennium. The C6 actually took a few years to grow on me, and now I like it as much (maybe more) as the C5 but the C5 is a truly classic design. That's the car I fell in love with back in high school, and the car that solidified my love for Corvettes. It will always be a great looking car
I think that while the popup scream '90s, they still look very nice. The part that has really aged on the C5 is the interior.
I remember the feeling I had when a neighbor of ours back in the 60's ( Before I was driving) bought a 1963 spit window coupe. I didn't have that same feeling until I saw my first C5. WOW!!! There are people driving Corvettes today that would never have dreamed they would until the C5 came out.
I still get people asking me if that's a new vette. They are shocked when I tell them its a 2002. Honestly, the vette is so sleek and aerodynamic, I don't think it will ever go out of style.