The 1990s just might be the definitive era of sad country music. For starters, some of the genre's all-time best storytellers and vocalists were at the top of their game during this period. Acts like George Strait, Garth Brooks and Alan Jackson were releasing some of their career songs in the '90s, and late legends like Naomi Judd and Joe Diffie were releasing the music we know and miss them for today.