With that in mind, I'll start with this car:

1997-1999 Chevrolet Corvette Convertible (C5)

Appears in EP 1.09, "Boca," at around 43:26.

It appears as an establishing shot for the Bada-Bing! strip club. I think it also appears in earlier episodes as the same way.

Currently, we have a C4 and C6 listed on the page, but not a C5.