A teen heartthrob when he started out, Frank Sinatra's career rose to legendary heights over the course of decades and dozens of hit songs. Whether due to a canny knack for finding the right arrangers—the likes of Quincy Jones, Neal Hefti, Nelson Riddle, Ernie Freeman and Johnny Mandel, to name a few—or possessing a familiar voice that grew up with a generation, Sinatra knew how to make a song work.
Likewise, Sinatra also knew his way around a recording session, as this seven-minute, fly-on-the-wall clip of the singer recording “It Was A Very Good Year” shows. Singing with a live orchestra, the Chairman of the Board puffs away on his cigarettes, keeps an ear out for bad notes, cracks jokes to keep the mood up and remains focused on the practical demands of the day, too, concerned that the song remain short enough for rigid radio formats.
Originally written by Ervin Drake and recorded Bob Shane with the Kingston Trio in 1961, “It Was A Very Good Year” was covered in 1965 by Sinatra, winning the Grammy Award for Best Vocal Performance, Male for the rendition a year later. Arranger Gordon Jenkins likewise took home a Grammy for the record—Grammy Award for Best Instrumental Arrangement Accompanying Vocalist(s).