First recorded (as a demo) by Jimmy Radcliffe (1964).
Hit released by Sammy Ambrose (US #117 1965)
Other 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 (who would later record with Bob Dylan, and found the group Blood, Sweat & Tears), Bob Brass, and Irwin Levine (‘Tie a Yellow Ribbon’, ‘Candida‘) in 1964. The song was first recorded as a demo that year by Jimmy Radcliffe in a session produced by Kooper.
“Sammy Ambrose, a Miami soul singer who had begun his recording career fronting the Afro-Beats, was the first to release a commercial single of ‘This Diamond Ring’, in December 1964. This was quickly followed by the January 1965 release of ‘This Diamond Ring’ by Gary Lewis & the Playboys. Both recordings appeared on Billboard magazine’s ‘Bubbling Under the Hot 100′ chart on January 9, 1965 – Ambrose’s recording at #117 and the Playboys’ recording at #101. But, that one appearance by Ambrose would mark his single’s only chart appearance while the Playboys continued the ascend the Hot 100 all the way to #1, on February 20, 1965, becoming the group’s only #1 single of their career.
“Ambrose’s biggest liability was that he didn’t have the same caché as being the son of a famous comedian (name recognition is everything in show biz) nor could make use off the chutzpah of producer Snuff Garrett, who promised radio disc jockey Murray the K a performance by the Playboys if he could break the Playboys’ record in New York City, and who also got Gary’s famous dad to call Ed Sullivan about booking an appearance on the The Ed Sullivan Show.
“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).
“The producer, Garrett, 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.
“Although the song has been his biggest commercial success as a songwriter, 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). 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” (1964):
Gary Lewis & The Playboys, “This Diamond Ring” (1965):
Al Kooper, “This Diamond Ring” (1976):