[h=2]2. 1942 Chrysler Convertible[/h] Source: Barrett-Jackson

Even after he found fame, Sinatra stayed a loyal Chrysler man. When he married his first wife Nancy Barbato in 1939, they reportedly drove off to honeymoon in a brand new 1939 convertible. And in a snapshot taken just as he became a household name, Sinatra is seen sitting proudly behind the wheel of a 1942 convertible, one of just 36,586 cars Chrysler managed to eke out before production was halted by America’s entry into World War II. Today, even without Sinatra’s provenance, these cars are highly collectible, the ’42 pictured above fetched $34,100 at Barrett-Jackson’s Las Vegas auction this year.