Deep Cuts From 1971: ‘Leaving On A Jet Plane’- Frank Sinatra. This song written in 1966 by a then unknown who went by the name John Denver- would become the only #1 hit that Peter, Paul and Mary ever had- in 1969. Denver would record it himself on his debut album. What I like about Sinatra’s version is it’s upbeat. The other versions I have heard have a sad feel to it, Sinatra’s – from his 1971 release Sinatra & Company- doesn’t.