Song of the Day: Gary Lewis & The Playboys, “This Diamond Ring”


“This Diamond Ring” was written by Al Kooper, Bob Brass, and Irwin Levine, and was recorded first by Sammy Ambrose, then by Gary Lewis (son of comedian Jerry Lewis). Gary’s version charted first, starting at #101 on Billboard‘s “Bubbling Under” chart on January 2, 1965. The following week, Ambrose’s version came in at #117 while Gary’s stayed at #101. Ambrose’s version dropped off the chart the following week, while Gary’s entered the Hot 100 at #65 and reached #1 on February 20.

19 thoughts on “Song of the Day: Gary Lewis & The Playboys, “This Diamond Ring”

  1. Great song! I was living in the Chicago-Land area of Indiana when this first hit the WLS airwaves. I was a big fan of Gary Lewis. Even bought the 45 record version of this song.

    Arlee Bird
    Tossing It Out


  2. Ah, yes, Jerry’s son.

    This diamond ring can be something beautiful and this diamond ring can be dreams that are coming true …and then your heart won’t have to break like mine did, if there’s love behind it …


    1. Al Kooper, who co-wrote the song, founded both The Blues Project and Blood Sweat & Tears. He wasn’t happy with Gary’s version and did his version later…

      Evidently he tried to get BS&T to do it and everyone else refused…


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