Costa's first arrangements for Sinatra were in 1961 for the production of Sinatra's ballad album Sinatra and Strings. Since then, Sinatra and Costa had a relationship that went on/off for several years until the late 1960s in which Sinatra hired Costa as his primary arranger. During this time, Costa arranged some of Sinatra's lowest-rated material in albums such as Cycles and A Man Alone as well as Sinatra's signature song "My Way."
Into the 1970s, Sinatra still used Costa as his primary arranger, but retired from music in 1972. Afterward, he returned with the Gordon Jenkins-arranged Ol' Blue Eyes Is Back that Costa supported with some minor charts in. Costa also aided in the arrangements of Sinatra's next album as well as his other 70s projects that didn't come into fruition. The remnants of his failed 70s projects were featured in the later discs of The Complete Reprise Studio Recordings.
Sinatra's 80s career featured only a minor essence of Costa as Costa died in 1982. He arranged the Present of Trilogy: Past Present Future as well as added in some minor arrangements into She Shot Me Down. Sinatra's final work with Costa was his final work conducting an album. Sinatra's collaboration album with Sylvia Syms was arragned by Don Costa.
- Below is a list of all albums Frank Sinatra recorded that were arranged by Don Costa:
- Sinatra and Strings
- My Way
- A Man Alone: The Words and Music of McKuen
- Some Nice Things I've Missed
- Syms by Sinatra
- Trilogy: Past Present Future
- She Shot Me Down
- Ol' Blue Eyes Is Back
- Sinatra & Company
- Sinatra and Strings personnel listing
- Cycles personnel listing
- A Man Alone personnel listing
- My Way personnel listing
- Ol' Blue Eyes Is Back personnel listing
- Some Nice Things I’ve Missed personnel listing
- Trilogy: Past Present Future personnel listing
- She Shot Me Down personnel listing
- Sinatra & Company personnel listing