| Had a No. 1 hit duet with daughter Nancy Sinatra, "Somethin' Stupid," in 1966. |
| Was the leader of the Rat Pack clique of celebrity pals, which included Joey Bishop, Sammy Davis Jr., Peter Lawford and Dean Martin. |
| His first No. 1 hit came in 1940 with "I'll Never Smile Again." |
| Won the talent show Major Bowes' Original Amateur Hour in 1935 as a member of the singing group the Hoboken Four. |
| Joined the Harry James Orchestra in the spring of 1939 and made his first recordings with the group in July of that year. Within six months, he left to join Tommy Dorsey's big band. |