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).