Some musical artists are pioneers, bringing a new way of performing. Frank Sinatra fell into that category when he turned away from crooning and embraced swing and jazz. In lists of favorite albums today, a Frank Sinatra CD will often appear. His appeal cuts across generations and some of his recordings have become unforgettable standards.

After singing with big band leaders, namely Harry James and Tommy Dorsey, Sinatra embarked on a solo career. His series of records for Capitol Records during the 1950s were praised by critics and the public. A compilation Frank Sinatra CD will always refer to tracks from these LPs. In the Wee Small Hours, released in 1955, marked the first collaboration between Sinatra and the arranger, Nelson Riddle. Riddle's arrangements suited the singer's delivery perfectly. One of the highlight tracks was Mood Indigo, co-written by Duke Ellington.

Sinatra and Riddle teamed up again for Songs for Swinging Lovers. This Frank Sinatra CD is more immersed in jazz and features Pennies from Heaven. Two Cole Porter compositions also appear, with I've Got You Under My Skin and Anything Goes. Billy May was the arranger on Come Fly With Me, which reached number one on the Billboard album chart in 1958. This was an early example of the concept album as all the songs concerned traveling. In addition to the title track, there was Chicago and South of the Border.

Sinatra left Capitol and founded his own record label Reprise Records. As rock music took hold in the 1960s, his star waned somewhat but Ol' Blue Eyes never went away. He would go on to announce several retirements, only to make a comeback. One of his biggest hit singles did occur in the midst of the swinging sixties when Strangers In the Night was a number one hit.  The song, for which he is most remembered, is of course My Way. No Frank Sinatra CD could possibly omit this song, said to be the most requested record at funerals!

The song was originally French and it was Paul Anka who wrote the English lyrics. It was a huge success, especially in the United Kingdom. Singers from every genre covered it, including Elvis Presley, Aretha Franklin, Glen Campbell and Tom Jones. Even Sid Vicious from punk band the Sex Pistols put out a version. Sinatra also did a duet of the song with opera star, Pavarotti, available on the Frank Sinatra CD Sinatra 80th: Live in Concert. Another duet can be found, with Willie Nelson, on Duets-Collector's Edition Set.