That friggin Olds that's pictured is butt ugly! But, the W30 was one of the fastest cars EVER made. A convertible was a plus, but I voted Olds because of the 'Hurst Olds' that a guy had my parents knew. White and gold....never a better lookin car since.
Second, I'd pick the Boss 351.
I had a Plymouth Roadrunner 383 and held several track records with it...I love ALL those old classics...my favorite that I owened was a '68 Mercury Cougar with a 428....although for daily driving I had a '67 Cougar with a modded 302...those WERE the days...