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This song was written by Al Kooper
, Bob Brass, and Irwin Levine. They originally came together under publisher Hal Webman and his company We Three Music, though they eventually turned to freelancing songs they had written. During this freelance period, they sold "This Diamond Ring" to Aaron Schroeder for $300. They originally wrote it with The Drifters in mind. The Drifters turned the song down, so next Bobby Vee's producer Snuff Garrett picked it up. Bobby Vee didn't want it, but Garrett found a good home for the song in a new band he discovered on a visit to Disneyland: Gary Lewis & the Playboys. He played the demo for Gary, who loved the song. When it was issued as the group's first single, it became a huge hit in America, and the first of seven Top-10 hits for the group.
Some of the top Los Angeles session musicians played on this track. These were some of the same folks who played on records by The Beach Boys and The Monkees, but unlike The Monkees, the Playboys did play on their songs. Regarding the musicians who performed on this and other tracks by the band, Gary Lewis told us, "The Playboys played on every track we ever did, the Wrecking Crew did solos and overdubs. I sang every song myself and had a backup singer that sang only harmonies with me. My producer Snuff Garrett can back up everything I've told you, and so can Leon Russell, who was the arranger of everything I did."
Some of the Wrecking Crew musicians Lewis refers to include Russell (piano), Tommy Alsup (guitar) and Hal Blaine (drums).
This song is a classic case of lyrical dissonance: the upbeat melody belies the melancholy lyrics, as the once shimmering diamond ring now represents a love that is lost. Despite the rather obvious meaning, Lewis tells us that people still misinterpret the song. "A lot of people love 'This Diamond Ring,' but they think it's a getting together song," says Lewis. "They say to me, 'Hey, we got married because of 'This Diamond Ring.'' I say, 'Really?' I mean, it's a breakup song."
This song was the beginning of a run of hits for Gary Lewis & the Playboys, which ended after Lewis was drafted and entered the army. Lewis credits his producer Snuff Garrett for making sure this wasn't their only hit. Said Lewis: "We're hearing it on the radio and we're all just flipping out beyond belief, because it's getting so much airplay and they wanted us to do all the local TV shows with the song. So we were flying real, real high. And Snuffy Garrett calls us in one day and says, 'Listen, you guys, I know it's exciting and all that. But you've got to calm down.' He says, 'You know how many one-hit artists there are out there?'"
The group followed this up with "Count Me In," which went to #2. Next was "Save Your Heart for Me," also a #2 hit.
In his book Backstage Passes and Backstabbing Bastards
, Al Kooper relates that he and his fellow songwriters, Brass, and Levine were "revolted" by the Playboy's version, because they'd removed the soul from what should have been an R&B song and "made a teenage milkshake out of it." Kooper in the same book goes on to recount: "To out surprise, after a hype-ridden sendoff on The Ed Sullivan Show
(once again, several of our songs were showcased by Sullivan acts), all you could hear on the radio was our turkey milkshake." The song eventually climbed up the charts to #1, pushing out "You've Lost That Lovin' Feelin'
Carving out room in the Pop landscape in 1965 was extremely difficult, as The Beatles were dominating the charts and still touring. It took a concerted promotional effort and some clever timing to get this song noticed. Snuff Garrett made sure to time the Gary Lewis & the Playboys releases so they didn't conflict with Beatles singles, and the band hit the road. Said Lewis, "Right when it came out we went on a Dick Clark Caravan of Stars tour with about ten other acts - six to eight weeks of one-nighters. And so we were always in the public eye, and whatever town we were going into we did local TV to promote the show for that evening. So we were constantly in the public eye. I think that's what it takes, along with a good record. That's what we did all those years."
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