Some of the shows on this list were amazing while others were notorious or just plain awful. Before you go accusing me of recent history bias, keep in mind that first twenty or so halftime shows featured either collegiate marching bands or Up With People.
1. U2 (Super Bowl XXXVI)
For the first Super Bowl after 9/11, the NFL invited U2 to play at halftime. Bono and the rest of the Irish rock band played "Beautiful Day," then performed a moving rendition of "Where The Streets Have No Name" as the names of the victims of the 9/11 attacks scrolled across screens erected behind the stage. Oh yeah, it was the first Super Bowl victory of the Patriots dynasty.
2. Janet Jackson and Justin Timberlake (Super Bowl XXXVIII)
If you don't remember this halftime show, you've been living under a rock. At the conclusion of a duet performance of "Rock My Body," Timberlake grabbed a piece of Jackson's outfit and ripped it off, fleetingly exposing her breast before the lights went black. This three-quarter second glimpse of jewelry-clad nipple sent the American people into a frenzy with Congressional hearings taking place and additional crackdowns by the FCC promised.
3. Michael Jackson (Super Bowl XXVII)
After years of lackluster halftime performances, the NFL decided that if it wanted people to keep from changing the channel during the break, it needed to invite headliners to the big game. And what headliner is bigger than the King of Pop himself? After performing "Billie Jean" and "Black Or White," Jacko was joined on stage by 3,500 children from the Los Angeles area for a rendition of "Heal The World." After the song, he ran around the stage kissing some of the youngest of the kids. Knowing what we now know about Jackson, watching clips of the children making their way to the stage is like watching lambs being led to the slaughter. (Say what you will about Jackson's supposedly-platonic love of children, the man knows how to work a crowd.)
4. Prince (Super Bowl XLI)
The repercussions of Nipplegate led the gun-shy NFL to select "safe" classic rockers to play future halftime shows. After restrained, lukewarm performances by Paul McCartney and the Rolling Stones, the NFL chose Prince to perform in Miami during Super Bowl XLI. Evidently, Prince missed the memo that he was supposed to tone things down and play to the over-50's corporate luxury box set. Master of theatrics that he is, Prince brought down the house in an electrifying performance, the highlight of which was his closing number, in which purple floodlights illuminated the raindrops of the first-ever Super Bowl downpour. Prince was therefore quite literally performing "Purple Rain" in purple rain.
5. Elvis Presto (Super Bowl XXIII)
In what was quite possibly the worst halftime show ever, "Be Bop Bamboozled" featured an Elvis impersonator who was also an illusionist (he called himself the Prince of Prestidigitation) singing songs from the 50's (no actual Elvis songs, however), all the while performing magic tricks. If the backup dancers in poodle skirts and the world's largest card trick failed to do it for you, the show also featured the world's first broadcast in 3-D, where viewers who had obtained special glasses from Diet Coke could put them on and see cartoons that popped out of the television during cutaways from Elvis Presto's show. If it's actually possible, the show was even worse than I'm making it sound.
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