no matter the year, anytime a ukelele-toting, falsetto-crooning hippy hits the charts with a cover of a 1926 showtune, it's going to be atypical.

Unlike a lot of the others being mentioned, he was not a harbinger of things to come, but a straightup anomaly. If you've ever sat through his Green Room performances from Monterey Pop, they're pretty painful. Hell, even the hit version is pretty painful: http://www.youtube.com/watch?v=90JCY0Eh1s4&feature=related