The Highwaymen - Cottonfields [#13] / The Gypsy Rover [#42] in 1961
The Kingston Trio - Jane, Jane, Jane [#93] / Scotch and Soda [#81] in 1962
I realize that The Weavers had several double-sided charting hits [e.g. Goodnight, Irene / Tzena, Tzena, Tzena] on the Decca label in the early 50s. I believe most of The Weavers Decca releases had orchestral backgrounds, even Wimoweh.
NOTE: I am limiting this discussion to 45rpm releases between 1955-1990. There obviously were double-sided hit singles before and after but I'm keeping to what I believe to be the peak time frame for 45s
My recent posting of Harry Belafonte's singles included one in which both sides charted [Cocoanut Woman/Island In The Sun]. This got me to thinking which 45rpm single had the highest combined peak positions on the Billboard Top/Hot 100 singles chart for both sides. The ultimate one would have had both sides reach #1. The one I could find that came closest was Elvis' 1956 single Don't Be Cruel/Hound Dog. Things get a little complicated because, until July 1958, BB had several different categories for ranking singles e.g. Top 100; Best Selling; Most DJ Plays; Most Jukebox Plays. For this Elvis release, each side reached #1 in several categories but not the Top 100 for both [Don't Be Cruel #1 / Hound Dog #2]. The next closest was The Beatles 1969 release of Come Together [#1] and Something [#3] on the now renamed Hot 100 chart.
Elvis was certainly The King for double-sided charted hits with 39. The Beatles and Fats Domino were 2nd, tied at 24. Elvis was 1st with Top 40 [25] and Top 10 [5] double-sided hits. The leaders in the Top 10 category are:
Elvis Presley - 5
Ricky Nelson / The Beatles - 4
Perry Como - 3
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