He wrote the words and music for "It Was a Very Good Year" in 1961, when a publisher friend told him that Bob Shane of the folk music group the Kingston Trio would be in the publisher's office the next morning, and the publisher asked Drake to write a song for Shane to sing solo. Shane recorded it for the album "Goin' Places" and other folk performers covered it. In a 2009 interview, Drake said that in 1965, Frank Sinatra had heard the song on his car radio as he was driving home in the desert and immediately pulled over in the middle of the night to a gas station and pay phone. He called Gordon Jenkins and told him he wanted him to make an arrangement with plenty of strings and maybe an interesting instrument like the oboe could be used as well. When he arrived back in L.A. he recorded it for his career comeback album "September of My Years". The Sinatra recording was a Top 30 single on the U.S. "Billboard" Hot 100 in 1966, and made No.1 on the Adult Contemporary chart.