Super Bowl 2023: Ranking the worst halftime shows ever

The Super Bowl draws 100 million people together … and the decision to watch the Super Bowl is literally the only thing that 100 million people could ever agree on. Sometimes the millions will find themselves transfixed by astounding musical moments during the halftime show, and sometimes they’ll find themselves unwitting witnesses to a cultural multi-car pileup.

The halftime show didn’t really begin catering to a national audience until several decades into the Super Bowl’s history, so we’ve excluded the marching band, children’s chorus and “Up With People” years. Instead, we’ll focus on the era when people who produced these shows really should have known better … or would figure out the error of their ways in about 12 minutes, give or take. We begin with a Beatle …

10. Paul McCartney (Super Bowl XXXIX, 2005): The ultimate Boomer Halftime Show. The NFL and halftime show producers needed to reel in what they thought was the halftime show’s trend toward raciness and immorality (gasp!), so in the wake of an infamous halftime show incident we’ll discuss below, the league brought in the most inoffensive performer possible. McCartney sauntered through a casual tour of Beatles and solo hits, kicking off a run of remember-when Boomer legends (the Stones, Bruce Springsteen, Tom Petty) that would hold the line with safe, family-friendly classic rock until the end of the decade.

9. Indiana Jones (Super Bowl XXIX, 1995): When is a halftime show not a halftime show? When it’s a straight-up commercial for an amusement park ride, an awkward middle-school-level dramatic performance with a multimillion-dollar budget. The 1995 halftime show was basically a televised version of a Disneyland Indiana Jones ride, and watching it was about as much fun as watching someone else enjoy a roller coaster. Whoever greenlit this mess chose poorly.

8. The Who (Super Bowl XLIV, 2010): One of the quintessential early rock bands ended up being the last rock band to date — and possibly ever — to headline the halftime show. Given that The Who were talking about breaking up as early as 1982, their Super Bowl halftime show four decades later wasn’t exactly cutting-edge appeal-to-the-youths material. Everybody just looked weary as the band cycled through a five-song medley of their greatest hits. The “hope I die before I get old” angle is tired, so let’s try this: Meet the new boss, so much worse than the old boss. Or maybe Old Man Wasteland.

7. “Winter Magic” (Super Bowl XXVI, 1992): Ah, these were more innocent days, an era when you could whip up an over-the-top Broadway spectacle with skaters and sparkles and holiday songs and call it a halftime show. You know what? Those more innocent days stunk. This Ice Capades silliness didn’t belong anywhere near an NFL field, and the league finally started shoving these productions off the stage soon afterward.

6. Black-Eyed Peas (Super Bowl XLV, 2011): Every generation gets its own chaotic-mess Super Bowl halftime show. It’s always a desperate grab for as much attention as possible by throwing familiar names together onstage, regardless of whether they can, you know, perform. The Black-Eyed Peas, Usher, Slash and hordes of local drill teams combined for an attempted musical stew that ended up more like neon-glowing sludge. Don’t be embarrassed that you used to like this stuff, everyone did. But let us never speak of Fergie’s attempt at “Sweet Child O’ Mine” again.

5. Blues Brothers (Super Bowl XXXI, 1997): This one’s bad right from the “Fox News Special Report” jump. Yes, there was a time when America was fascinated by a bunch of comedians dad-dancing to classic R&B. No, we don’t know why either. Not even appearances by ZZ Top and James Brown can redeem this catastrophe, although it’s funny to think about little kids all over the country asking their parents what “Tush” is.

4. It’s A Small World (Super Bowl XXV, 1991): The whiplash of going from Whitney Houston’s transcendent national anthem to this gloppy Disney mess should’ve put viewers in concussion protocol. Is it wrong to hate on a halftime show made up entirely of kids? If said kids are singing “It’s A Small World,” hating on the show is practically your patriotic duty. If you’re tempted to complain about current halftime shows, take a good hard look at what your parents and grandparents had to put up with, and stop complaining.

3. Aerosmith, Britney Spears, N’Sync, Nelly, Mary J. Blige (Super Bowl XXXV, 2001): Just a flat-out mess. This was the equivalent of “You like pizza, burgers, wings and tacos? How about a pizza-burger-wing taco!” In attempting to appeal to everyone, this dog’s breakfast of musical styles (and fashion) ends up collapsing in an incredibly awkward “Walk This Way” strut-dance-singalong. Hey, it was 2001, nobody knew any better.

2. Elvis Presto (Super Bowl XXIII, 1989): We defy you to get through this video of an Elvis-impersonating magician – “Elvis Presto,” of course — without cringing so hard you pull a muscle. Mr. Presto lip-syncs his way through an attempted card trick — “Everybody in the stands, let’s hear it for your card because the choice depends on your applause” — that falls apart, and the 3-D glasses didn’t quite work as advertised. Utter nonsensical chaos, but then you don’t make a huge miss if you don’t take a huge swing.

1. Janet Jackson & Justin Timberlake (Super Bowl XXXVIII, 2004): Another hodgepodge throw-it-all-at-the-wall halftime show — everyone from Nelly to Jessica Simpson to Kid Rock was on stage at one time or another — culminated in one of the most infamous moments shown on TV, as Justin Timberlake tore off part of Janet Jackson’s bustier to reveal — gasp! — her nipple. The performance itself was fine in a typical over-the-top halftime show way, but the backlash, from the destruction of Jackson’s career to the way Timberlake skated to the overwrought public moral posturing, made this moment one of the most notorious in American entertainment history. The backlash from this moment would rattle popular culture for years, and for no good reason at all.