15 of the Worst Super Bowl Halftime Performances

Aside from the commercials and maybe the game itself, the halftime show is the most anticipated part of the Super Bowl each year. And while there have been some spectacular performances in years past, there have also been some trainwrecks. With Madonna performing at this year’s Super Bowl this weekend, we’re all waiting and wondering how good or bad the show will be.

Super Bowl XXXVII (2003): Shania Twain, No Doubt, Sting


Shania Twain’s performance of “Man! I Feel Like a Woman” wasn’t all that bad, but seriously, did she think most of the MEN watching the Super Bowl would be able to relate to it?

Super Bowl XLII (2008): Tom Petty and the Heartbreakers


Tom Petty and his Heartbreakers is a great band, but their performance at Super Bowl XLII fell flat and wasn’t the least bit exciting.

Super Bowl XLIV (2010): The Who


Apologies to fans of The Who, but this band is past their prime. Their halftime performance was bland and boring with no wardrobe malfunctions.

Super Bowl XLV (2011): Black Eyed Peas feat. Slash and Usher


They sounded terrible and failed to impress anyone at all.

Super Bowl XXXVIII (2004): Janet Jackson, P. Diddy, Nelly, Kid Rock, and Justin Timberlake


Janet Jackson and Justin Timberlake performed a shocking number that is now referred to as “Nipplegate.” It was officially called a “wardrobe malfunction” and because of Janet’s bare nipple on live tv MTV is no longer producing halftime shows and live tv is now five-second delay tv.

Super Bowl XXIX (1994): Indiana Jones, Tony Bennett, Patti LaBelle, Arturo Sandoval, Miami Sound Machine

At least Indiana Jones didn’t sing, but it couldn’t have been much worse if he had. During this halftime performance there was a knockoff Indiana Jones who was definitely not Harrison Ford and the whole thing seemed like an ad for the Indiana Jones ride at Disney.

Super Bowl XXVI (1992): Gloria Estefan with Brian Boitano and Dorothy Hamill

Ah, the magic of winter. Really? The holidays are over by the time the Super Bowl comes around and we’re all ready for springtime anyway. However, since this Super Bowl was in Minnesota, we were all supposed to be entertained by Frosty and figure skaters. We weren’t.

Super Bowl XXIII (1989): Elvis Presto


Some lunatic called Elvis Presto tried to perform the “World’s Biggest Card Trick” and failed miserably. It was painful to watch and one of the biggest disappointments in halftime history. Come on, an Elvis impersonator should at least look a little like Elvis!

Super Bowl XXXIV (2000):Christina Aguilera, Enrique Iglesias and Phil Collins, Toni Braxton

Christina Aguilera makes the list, but really not for her performance, because it was kind of okay… unlike her rendition of the national anthem. All in all, this performance was way too sappy for a Super Bowl halftime show.

Super Bowl XX (1986): Up With People

Up With People have performed in several halftimes over the years; God only knows why. These corny, uber-happy goofballs are sweet enough to give you a toothache.

Super Bowl XXXV (2001): Aerosmith, N’Sync, Britney Spears, Nelly, Mary J. Blige

This weird halftime show featured a bizarre mishmash of addicts screaming “Walk This Way” with Aerosmith.

Super Bowl (1993): Michael Jackson with an Assload of Kids

Any reason why this wasn’t a good idea? I wonder if they all spent the night with him that night.

Super Bowl XXII (1988): Chubby Checker and the Rockettes

Chubby Checker wasn’t all that bad, but he’s just another example of an artist past their prime being featured at a Super Bowl halftime. I’m sure Grandpa loved it though.

Super Bowl XXV (1991): New Kids on the Block, It’s a Small World, and Warren Moon

New Kids on the Block and one of the most annoying rides at Disney made this halftime like nails on a chalkboard.

Super Bowl XXX (1996): Diana Ross

Despite being about 20 years past her prime, the entire halftime of Super Bowl XXX was devoted to Diana Ross. At the end, she left in a helicopter.

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