5. Series 61 "Sedanette"

Year: 1948
Complex Says: The swooping fastback of the '48 Sedanette makes it one of the most dramatic cars of the '40s. It has such incredible presence, and it truly embodies the intimidating nature of Caddys of bygone eras. Just look at the sleek upward curve of the tailfins that would soon grow to be such a dominating design element in the '50s.