Carol Channing (Super Bowl IV, 1970): Granted, Carol Channing doesn’t exactly scream “outrageous,” but she holds a place in Super Bowl history as the first non-marching-band entertainment.
The Black-Eyed Peas (Super Bowl XLV, 2011): The Peas’ Tron-knockoff electro-light show looked cool as it was happening.
Paul McCartney (Super Bowl XXXIX, 2005): In the immediate wake of the wardrobe malfunction, the Super Bowl halftime organizers went for the most inoffensive selection they could possibly find.
Madonna (Super Bowl XLVI, 2012): About 114 million people watched Madonna’s performance, which was three million more than the actual game.
Aerosmith/Britney Spears/N’Sync/Mary J. Blige/Nelly (Super Bowl XXXV, 2001): Here’s the tipping point in Super Bowl halftime shows, the more-is-more, over-the-top blowout buffet with a little something for everyone.
Michael Jackson (Super Bowl XXVII, 1993): It’s tough to overstate how awful Super Bowl halftime shows used to be. Once someone finally realized that the most-watched TV show of the year actually could attract some of the top musical talent in the world, halftimes took a huge leap forward in quality. We all owe MJ a debt of gratitude, otherwise we’d still be watching unknown gymnastics troupes desperately gyrating for our attention.
Janet Jackson/Justin Timberlake (Super Bowl XXXVIII, 2004): And here we have it: The most significant moment in halftime show history, and indeed one of the landmark moments in American pop culture.