Best Ever: 96 Rock, early 1980s. Wake Up Crew, Up Yours Friday (a G-rated version of the FU Line), Poetry Corner, Mr. B and the B-Team, Bachelor Cookbook, Helium Monday, Rock & Roll Preppy t-shirts, Album Hour (RIAA won't let you do that anymore), Electric Lunch, 96Rockards (still have mine).
This was prior to the "cool it with the heavy metal, give us 'Pure Rock & Roll'" classic rock era of the mid-80s, which resulted in a fallow period for 96 Rock before Z-93 showed them the right way to do classic rock and 96 Rock went back to the straight-ahead AOR that made them famous.
Honorable Mention: 96 Rock and Z-93, late 80s/early 90s when they both worked hard as heck to grab the same AOR listeners. Lake 102. Fox 97 and Wide 107 before they moved in to Atlanta and dropped Top 40 for AC (and then oldies and country, respectively). Me and my radio geek friends would try to DX Fox and WWID from any radio we could--much broader playlists than Z-93. Star 94 and B98.5 with their 70s/80s nights on Friday/Saturday. Power 99 late 80s, expanding what a Top 40 station could do.
Worst Ever: 99X, after the first couple years and their format got set in their ways, and when "alternative new rock" became a contradiction in terms.
Dishonorable Mention: Star 94 except when doing 70s/80s nights. Heave & Ikki. Z-93's "churban" era (late 80s prior to classic rock). 94.9 Lite FM. 95.5 The Beat.