Introduction:
“This Diamond Ring,” recorded by Gary Lewis & the Playboys, became an iconic pop-rock hit upon its release in 1965. Written by Al Kooper, Bob Brass, and Irwin Levine, the song was initially intended as a soulful ballad, reflecting on the lost significance of a diamond ring after a breakup. Originally recorded by singer Sammy Ambrose, it was producer Snuff Garrett who envisioned Gary Lewis & the Playboys bringing a pop sound to the song, and the version quickly topped the Billboard Hot 100 in February 1965.
The recording involved top studio musicians from the Wrecking Crew, including Hal Blaine on drums, Joe Osborn on bass, and Leon Russell on keyboards. This combination, along with Gary Lewis’s heartfelt vocals, helped create a polished yet relatable sound. While “This Diamond Ring” marked Gary Lewis & the Playboys’ breakthrough, Al Kooper reportedly felt it lacked the soulful depth he initially intended, imagining it for a group like The Drifters.
The song’s success launched Gary Lewis & the Playboys into stardom, sparking a series of hits throughout the mid-1960s. The track remains a classic example of 1960s pop, embodying both the heartbreak and catchy melodies of the era.