9. He was a founding member of the 1960s Rat Pack
. The first supergroup of multi-talented stars, the Rat Pack -- Sinatra, Sammy Davis Jr., Dean Martin, Peter Lawford, and Joey Bishop -- never referred to themselves by that name, instead calling themselves the Summit or the Clan. But the press loved the moniker, and the Rat Pack stuck. Along with Davis Jr. and Martin, Sinatra was considered one of the leaders of the group.
8. He shared a famous woman with Woody Allen. From 1966 to 1968, Sinatra was married to actress Mia Farrow, who was thirty years his junior. In 1980, she began an ill-fated 12-year relationship with Allen, who would leave her for one of their adopted children.
7. He learned music by ear. Sinatra never learned to read music, and did well enough hitting pitch without learning how to translate notes on paper. He was obviously way too cool for that.
6. He founded Reprise Records. The Sinatra nickname, "Chairman of the Board," was born in 1960, the year he founded Reprise. The label, which Sinatra sold to Warner Bros. Records in 1963, went on to boast a roster that included Joni Mitchell, Neil Young, Captain Beefheart, Frank Zappa, T. Rex, The Beach Boys, Fleetwood Mac, Green Day, Mastodon, My Chemical Romance, and Disturbed.