Claim: Frank Sinatra collaborated with Duke Ellington in 1968.

Francis Albert Sinatra -LRB- -LSB- sᵻˈnɑːtrə -RSB- -LSB- siˈnaːtra -RSB- ; December 12 , 1915 -- May 14 , 1998 -RRB- was an American singer , actor , and producer who was one of the most popular and influential musical artists of the 20th century . He is one of the best-selling music artists of all time , having sold more than 150 million records worldwide . Born in Hoboken , New Jersey , to Italian immigrants , Sinatra began his musical career in the swing era with bandleaders Harry James and Tommy Dorsey . Sinatra found success as a solo artist after he signed with Columbia Records in 1943 , becoming the idol of the `` bobby soxers '' . He released his debut album , The Voice of Frank Sinatra , in 1946 . Sinatra 's professional career had stalled by the early 1950s , and he turned to Las Vegas , where he became one of its best known performers as part of the Rat Pack . His career was reborn in 1953 with the success of From Here to Eternity , with his performance subsequently winning an Academy Award and Golden Globe Award for Best Supporting Actor . Sinatra released several critically lauded albums , including In the Wee Small Hours -LRB- 1955 -RRB- , Songs for Swingin ' Lovers ! -LRB- 1956 -RRB- , Come Fly with Me -LRB- 1958 -RRB- , Only the Lonely -LRB- 1958 -RRB- and Nice 'n' Easy -LRB- 1960 -RRB- .   Sinatra left Capitol in 1960 to start his own record label , Reprise Records , and released a string of successful albums . In 1965 , he recorded the retrospective September of My Years , starred in the Emmy-winning television special Frank Sinatra : A Man and His Music , and released the tracks `` Strangers in the Night '' and `` My Way '' . After releasing Sinatra at the Sands , recorded at the Sands Hotel and Casino in Vegas with frequent collaborator Count Basie in early 1966 , the following year he recorded one of his most famous collaborations with Tom Jobim , the album Francis Albert Sinatra & Antonio Carlos Jobim . It was followed by 1968 's collaboration with Duke Ellington . Sinatra retired for the first time in 1971 , but came out of retirement two years later and recorded several albums and resumed performing at Caesars Palace , and reached success in 1980 with `` New York , New York '' . Using his Las Vegas shows as a home base , he toured both within the United States and internationally until a short time before his death in 1998 .   Sinatra forged a highly successful career as a film actor . After winning an Academy Award for From Here to Eternity , he starred in The Man with the Golden Arm -LRB- 1955 -RRB- , and received critical acclaim for his performance in The Manchurian Candidate -LRB- 1962 -RRB- . He appeared in various musicals such as On the Town -LRB- 1949 -RRB- , Guys and Dolls -LRB- 1955 -RRB- , High Society -LRB- 1956 -RRB- , and Pal Joey -LRB- 1957 -RRB- , winning another Golden Globe for the latter . Toward the end of his career , he became associated with playing detectives , including the title character in Tony Rome -LRB- 1967 -RRB- . Sinatra would later receive the Golden Globe Cecil B. DeMille Award in 1971 . On television , The Frank Sinatra Show began on ABC in 1950 , and he continued to make appearances on television throughout the 1950s and 1960s . Sinatra was also heavily involved with politics from the mid-1940s , and actively campaigned for presidents such as Harry S. Truman , John F. Kennedy and Ronald Reagan , though before Kennedy 's death Sinatra 's alleged Mafia connections led to his being snubbed .   While Sinatra never formally learned how to read music , he had an impressive understanding of it , and he worked very hard from a young age to improve his abilities in all aspects of music . A perfectionist , renowned for his dress sense and performing presence , he always insisted on recording live with his band . His bright blue eyes earned him the popular nickname `` Ol' Blue Eyes '' . Sinatra led a colorful personal life , and was often involved in turbulent affairs with women , such as with his second wife Ava Gardner . He went on to marry Mia Farrow in 1966 and Barbara Marx in 1976 . Sinatra had several violent confrontations , usually with journalists he felt had crossed him , or work bosses with whom he had disagreements . He was honored at the Kennedy Center Honors in 1983 , was awarded the Presidential Medal of Freedom by Ronald Reagan in 1985 , and the Congressional Gold Medal in 1997 . Sinatra was also the recipient of eleven Grammy Awards , including the Grammy Trustees Award , Grammy Legend Award and the Grammy Lifetime Achievement Award . After his death , American music critic Robert Christgau called him `` the greatest singer of the 20th century '' , and he continues to be seen as an iconic figure .