BLAME IT ON THE RAIN, YEAH, YEAH: One of my occaisional forays into Wikipedia revealed an interesting topic for discussion--who is the most embarassing ever Grammy Winner for Best New Artist? (Milli Vanilli, which had its Grammy stripped from it, is, of course, disqualified.) Sure, you can ask "Wow, whatever happened to Shelby Lynne?," but the out and out embarassments come in the 60s, which featured winners Robert Goulet, The Swingle Singers, Tom Jones, Bobbie Gentry, and Jose Feliciano. Of course, the 1963 Grammys may be the most bizarre ever, with Vaughn Meader winning the big award.
Conversely, who's the best choice the Grammy folks have made based on longevity, etc.? 1970 (Crosby Stills & Nash), 1972 (Carly Simon), 1974 (Bette Midler), 1991 (Mariah Carey), and 1995 (Sheryl Crow) would probably lead the list (assuming you exclude the Beatles, who won in 1965).