399. Kenny Rogers
The first thought of Kenny Rogers these days may revolve his ill advised plastic surgery but there was a time when Rogers was the undisputed king of Country Pop and his crossover appeal was off the charts. Ironically, this could work against him in terms of the Rock and Roll Hall, as he was not Rock enough for the Hall nor was he Country enough to have the same respect that the Outlaw musicians had. Still, there would be much more bizarre Country based choices than “the Gambler”.