5. 1971 Chevrolet Impala Convertible

Movie Title: Fear And Loathing In Las Vegas (1998)
Driver: Dr. Gonzo and Hunter S. Thompson
Played By: Benicio Del Toro and Johnny Depp

Complex Says: It was a tough call between this and the 1971 Cadillac Fleetwood Eldorado that also shows up in this film. Double convertible bonus.