Super Bowl XXIII
For the first quarter century of Super Bowls, organizers had yet to figure out the "throw a bunch of big musical acts at the problem" style of halftime show planning. Which explains Super Bowl XXIII’s big production, titled Be Bop Bamboozled in 3-D. It starred Elvis Presto (a low-end Presley impersonator) performing card tricks (!) while decked out like the illegitimate son of Dame Edna and Andrew Dice Clay. So there’s that.
Super Bowl XXV
Believe it or not, Disney has a long, storied history of mucking up the big game. Take for instance that time Big Mouse got his white gloves all over the 1991 Super Bowl. The end result: kids and costumed characters getting their groove on in front of a massive two-dimensional castle that looks nothing like the one at the Magic Kingdom. All the while, sinister 50-foot statues of Goofy, Donald, Pluto, and the gang look on.
Super Bowl XXVI
The premise: to combine cellos, gymnastic mats, and sequined cheerleaders (zillions of them) with Olympic figure skaters Brian Boitano & Dorothy Hamill. Oh, and we’ll place the latter on tiny ice rinks, ‘cause hey, ice ain’t free, Jack! Hey guys, why not pick just ONE awful theme and go with it?
Super Bowl XXXVII
Look, it’s Shania Twain, well past her creative sell-by date! And what’s this? Why it’s Sting! And he’s playing Message in a Bottle. Not with the other guys in the Police, mind you (who’d have done it in a heartbeat) – he’s with Gwen Stefani! MUCH better! I think I’m being sarcastic! That’s soooo clever of me!
Super Bowl XXXIV
So for some reason you’ve got Phil Collins, Christina Aguilera, and Enrique Iglesias – together. That’s questionable enough. But then producers add in an 80-piece orchestra and a Disney-infused Lion King-style affair. You know, just to really laugh in the face of the entire football-loving demographic.
Super Bowl XXXVIII
This one’s a no-brainer: Janet Jackson going head-to-head with Justin Timberlake on his mega hit Rock Your Body. At the end of the tune, J.T. rips away part of Janet’s top to reveal her exposed, uh, girl part. Although everyone involved claims it was a "wardrobe malfunction" (a previously non-existent term, btw), this seems questionable given the offending action takes place just as he sings "gotta have you naked by the end of this song."
Super Bowl XXIX
Okay, where to begin with this? We’ve got an awful Indiana Jones impersonator (guh?), who, while sporting an ill-fitting leather jacket, does battle with hundreds of ambiguously ethnic-looking dancing guys, risking his life to nab what appears to be a $40 urn. Clearly this is too much of a good thing – minus the, uh, ‘good.’ So it’s too much of a thing, I guess. Producers: Disney. Uh-huh.
Super Bowl XXXV
Britney Spears, 'N Sync, and Aerosmith. On the same bill. At the same time. Is this as bad as it sounds? No, of course not. It’s eleven times worse than it sounds. Plus three.
Super Bowl XX
Another go-to strategy for early Super Bowls involved bringing in the Up With People folks. Basically, they were a bunch of dopey, happy whitebread guys n’ gals doing watered-down versions of songs we never liked to begin with. The Simpsons once parodied their lameness with a halftime show starring the fittingly-titled Horary for Everything. That says it all.
Super Bowl XXXI
Musical guests: the Blues Brothers! Which would have been cool if this were 1983. Which it wasn’t – this was 1997. Meaning Jim Belushi and John Goodman were filling in for the not-so-alive John Belushi. Oh, and the whole thing was a plug for their upcoming flick Blues Brothers 2000 (in which I was an extra, full disclosure), an awful, awful piece of cinematic awfulness.