When: 2001, Super Bowl XXXV, Baltimore Ravens (W) vs. New York Giants (L)
Who: Aerosmith, Britney Spears, 'N Sync, Mary J. Blige, Nelly
Boom: Five geetar-worshippin' old-timers versus a veritable hit team assembled by halftime producers from MTV at the height of TRL. This was the network's last gasp of greatness, and they used it to pit hale-and-hearty youth against a rock band gasping for air. Hella tight, yo.
Bust: The "Walk This Way" rap-rock redux, swapping out Run-DMC for a bunch of popsters.