What 20's, 30's, 40's Song Are You Listening To Now (sinatra, record)
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I think I like more music from that era than my parents do. I've linked to a fair amount of it on the jazz thread. For stuff that's either more "pop" sounding or country/bluegrass of that era: The Andrews Sisters, Vera Lynn, Peggy Lee (although she might still count as just jazz), some Doris Day, some Bing Crosby, some of The Ink Spots, Bill Monroe, and Ed Haley.
Given that Little Willie John didn't write "Fever" until 1956, it wouldn't fit into a "20s, 30s, 40s" thread. Although Peggy did become a star in the '40s, she didn't do that song until the late '50s. I don't think there's a bad version of that song.
Keeping to the subject of this thread - how about the real inventor of Rock 'N' Roll, the great Louis Jordan (the term "Rhythm and Blues" was invented to describe his music in the mid-40s):
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