First recorded (as a demo) by Jimmy Radcliffe (1964).
First released by Sammy Ambrose (US #65 1965).
Hit version by Gary Lewis & The Playboys (US #1 1965).
Also recorded by Al Kooper (1976).
From the wiki: “‘This Diamond Ring’ was written by Al Kooper, Bob Brass, and Irwin Levine in 1964. The song was first recorded as a demo that year by Jimmy Radcliffe in a session produced by Kooper.
“In 1965, Sammy Ambrose recorded ‘This Diamond Ring’ as the first commercial release of the song. Ambrose, a Miami-born singer, had begun his recording career fronting the Afro-Beats (which included members of Betty Wright’s family). But, the song was also covered very shortly thereafter by Gary Lewis & The Playboys. Lewis’s version charted first, #101 on the January 2, 1965; both versions – Ambrose’s and Lewis’ – were together on the Billboard Hot 100 the following week; Ambrose’s recording stalled at #65 while Lewis’ version continued advancing to #1, making it to the top-of-the-chart on February 20.
“None of the Playboys played their instruments on the hit recording and Lewis’s vocals were heavily supported by Ron Hicklin’s overdubs. The music was performed by members of The Wrecking Crew, including Hal Blaine (drums), Carol Kaye (bass) and Leon Russell (keyboard).
“Snuff Garrett, who produced the Lewis recording session, recalls that it took a concerted promotional effort and some clever timing to get this song and others by The Playboys noticed amidst the still-prevailing pop music atmosphere of Beatlemania and the British Invasion. Garrett made sure to time the Playboys’ releases so they didn’t conflict with Beatles singles, and the band would immediately hit the road to tour behind each single release. There were two additional Top 5 hits for the Playboys before Lewis was drafted into military service.
“Al Kooper (later a founding member of Blood, Sweat & Tears) has reportedly stated many times that he was unhappy with the Lewis recording and had originally hoped the song would be recorded by a group like The Drifters (based upon the original demo he’d produced with Jimmy Radcliffe), although the song has been his biggest commercial success as a songwriter. Kooper would later re-visit the song, himself, recording a funky version for his 1976 album Act Like Nothing’s Wrong.”
Sammy Ambrose, “This Diamond Ring” (1965):
Gary Lewis & The Playboys, “This Diamond Ring” (1965):
Al Kooper, “This Diamond Ring” (1976):