Top of the Charts: “This Diamond Ring” by Gary Lewis & the Playboys
- joearubenstein
- Feb 20
- 1 min read
Feb. 20, 1965 - Hitting No. 1 on the Billboard Hot 100 today was “This Diamond Ring,” single by Gary Lewis & the Playboys. The song was written by Al Kooper, Bob Brass, and Irwin Levine.
The group began life as Gary & the Playboys. Gary Lewis, son of comedian Jerry Lewis, started the band with four friends of his when he was 18. Joking at the lateness of his bandmates to practice, Lewis referred to them as “playboys,” and the name stuck.
They auditioned for a job at Disneyland without telling Disneyland employees about Lewis’ celebrity father. They were hired on the spot, audiences at Disneyland quickly accepted them, and the Playboys were soon playing to a full house every night.
The orchestra bandleader Les Brown, who had known Jerry Lewis for years, had told record producer Snuff Garrett that the younger Lewis was playing at Disneyland. After listening to the band, Garrett thought using Gary’s famous name might sell more records, and convinced them to add “Lewis” to their name.
Garrett brought them to a studio with “This Diamond Ring” in a session financed by Jerry Lewis’ wife Patti. Garrett wanted to maximize the chances for a hit, so he insisted on using experienced session musicians for the overdubs, which included guitar and keyboard solos, additional bass and drum overdubs, and timpani.

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