Al Kooper and the Son of Jerry Lewis Created 60s Magic, but One of Them Wasn’t Crazy About It

What happens when the son of a famous comedian and movie star teams up with the guy who played the organ part on “Like A Rolling Stone”? It’s not a rhetorical question but rather what actually occurred to produce the surprising No. 1 single “This Diamond Ring”.

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Technically, there were plenty of others involved, and the “Like A Rolling Stone” part was played a few months after “This Diamond Ring” turned into a runaway success. Nonetheless, unlikely collaborators certainly helped Gary Lewis & The Playboys to a monster hit in 1965.

Gary, Not Jerry

Gary Lewis probably knew that getting into show business in the world of television and film would only invite unfair comparisons to his father, the legendary Jerry Lewis. Instead, Lewis chose the path of a professional musician, playing drums and singing with a band he dubbed the Playboys.

The group snagged an early gig playing at Disneyland. Eventually, they were discovered there by producer Snuff Garrett, who encouraged Lewis to include his surname in the band name to attract some attention. Garrett started looking for material for the group.

A song called “This Diamond Ring” landed on Garrett’s desk. The three writers had penned it in the hopes of an R&B act getting a hold of it. They weren’t all that pleased with the somewhat chirpy, teeny-bopper arrangement delivered by Gary Lewis & The Playboys. One of those writers was an up-and-coming musician named Al Kooper.

“Ring” True

Kooper was just starting out his career and had landed a gig writing songs for a publishing outfit out of New York City. He penned “This Diamond Ring” with Irwin Levine and Bob Brass, thinking that a group like The Drifters would be the ideal act to bring it to life. Their complaints about Lewis and company’s take faded a bit when the royalty checks for a No. 1 single started rolling in for them.

To make that happen, Lewis’ mother financed the recording. Gary Lewis has always contended that his backing band played on those sessions. But it’s very possible that the snappy track benefited from the participation of members of The Wrecking Crew, the elite session players found on the West Coast.

“This Diamond Ring” started a string of big hits for Lewis and his band. They managed to score at a time when the charts were dominated by British Invasion acts. Over the years, stellar musicians like bassist Carl Radle and drummer Jim Keltner were part-time Playboys before moving on to more memorable gigs.

Behind the Lyrics of “This Diamond Ring”

Don’t be fooled by the title and the peppy music. “This Diamond Ring” actually tells a tale of woe. The narrator is desperate to rid himself of the ring after his girl returns it to him. “Who wants to buy this diamond ring?” Lewis asks. “She took it off her finger, now it doesn’t mean a thing.

In the refrains, he explains that the jewelry in question might serve a purpose for someone else. “This diamond ring can be something beautiful,” Lewis sings. “And this diamond ring can be dreams that are coming true.”

So if you’ve got someone whose love is true,” the narrator says. “Let it shine for you.” “This Diamond Ring” certainly shone bright for Gary Lewis & The Playboys. And it also introduced much of the music world to Al Kooper, reluctant as he was to take credit for a song that got away from him.

Photo by Archive Photos/Getty Images

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