I'm preparing a new chronological post, but until then I'm updating with my current obsession, Del Shannon.
Shannon was an early 60s pop singer/songwriter, generally discarded as a mere sub-Beatles teen idol. But his songs generally have a weird, distressed undercurrent of abandonment and loneliness ("Misery") that floats them far above the usual teen-idol fare. Or with songs like "Hats Off to Larry", which is about Del cheering for the guy who broke his ex-girlfriend's heart--and, awesomely enough, Del wants his ex to know that even though her new man has thoroughly broken her, he (i.e. Del) still wants her back. Lesson: don't ever leave me.
He had a few big hits in the mid-60s ("Runaway"), but his tendency towards lyrical heartbreak eventually became full-blown clinical depression and he was ultimately a drunk and a suicide. He's also one of the few male singers to make falsetto sound cool. Check him out.
Del Shannon - Misery
Del Shannon - Hats Off to Larry
Del Shannon - Little Town Flirt
Del Shannon - Do You Want to Dance
Del Shannon - Stranger in Town
Del Shannon - Break Up
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