[h=2]9. 1981 Chrysler Imperial ‘FS Edition’[/h] Source: Fiat Chrysler Automobiles

Sinatra liked his friends to be movers and shakers, and by the late ’70s he’d become close friends with Chrysler chief Lee Iacocca. As Iacocca moved to transform Chrysler into a profitable maker of affordable front-wheel drive vehicles, he also sought to revive the Imperial nameplate for a flagship personal luxury coupe to take on Cadillac Eldorado and Lincoln Continental Mark VI. Enlisting Sinatra’s star power to help sell the cars, Chrysler launched the Imperial “FS Edition,” with paint and interior to match Sinatra’s eyes, plus a special box under the dashboard that held 10 Sinatra cassettes. Unfortunately, reliability issues meant the $20,988 car was a huge flop for the brand, and it sold just 12,385 Imperials between 1981 and ’83 – with just 278 of them being FS Editions.