The Academy Awards ceremony has, after many, many decades, become an event we both eagerly await and woefully dread. The latter emotions come from the overwrought parade of celebratory adulation for the Hollywood system, an annual ritual that regularly surpasses the three-hour mark. It doesn’t help that in between the awards and tributes to cinematic history are often awkwardly placed musical numbers that seem to make the night drag on even longer. Looking back at the last 25 years, there have been some awesomely atrocious performances in Oscar history. We’ve narrowed down these many missteps and present ten of the most memorable.
Rob Lowe sings with Snow White
This is perhaps the most infamously awful musical montage: the opening number from the 1989 ceremony, featuring Disney’s first animated princess cavorting with Hollywood luminaries like Merv Griffin, Doris Day, Cyd Charisse, and Rob Lowe (fresh off a sex-tape scandal), is completely hands-down bat-shit crazy.
Savion Glover tap dances in honor of Saving Private Ryan
Fame‘s Debbie Allen popped up as choreographer several times for Oscars ceremonies in the ’90s, often bringing along some of her interpretive dancing buddies. Here, at the 71st Academy Awards, she tapped Savion Glover, among others, to interpret the dramatic scores from films like Saving Private Ryan and The Thin Red Line. Tap dancing certainly does justice to the atrocities of World War II, doesn’t it?
Crash, interpreted through dance
Not only did Crash infamously win Best Picture over the overwhelming favorite Brokeback Mountain in 2006, but the performance for the nominated song from the film involved singer Kathleen Bird York belting in front of a flaming set piece in which dancers recreated scenes from the film — just in case the movie itself wasn’t literal enough for you.
Seth MacFarlane sexually harasses the audience
Last year’s ceremony, hosted by Family Guy creator Seth MacFarlane, was full of insufferable and offensive jokes, but MacFarlane really set the tone early in the night with this song poking fun at all of the actresses present who had appeared nude on film. (Who doesn’t think Jodie Foster’s rape scene in The Accused is downright hilarious?!)
Robin Williams channels South Park
Can you believe how SHOCKING and CRAZY it was that the classic song from South Park: Bigger, Longer, and Uncut was nominated for an Oscar? For some reason, the producers tapped Robin Williams to perform “Blame Canada,” which only undercut the faux-shocking nature of it all.
Nell Carter sings “Friend Like Me”
Where was Robin Williams the year Aladdin was nominated for Best Original Song? Well, maybe it’s for the best, because how often does one get to see Nell Carter sing on stage flanked by dozens of ribbon dancers?
The Lord of the Dance explains film editing
The mid-’90s, or “The Michael Flatley Years,” were a real dark time for global culture. Here’s the Lord of the Dance himself, prancing about in leather arm and wristbands in an homage, apparently, to the storied history of film editing.
Tim Curry, Mara Wilson, Kathy Najimy make us confused
Tim Curry, Kathy Najimy, and Mara Wilson performed “Make ‘Em Laugh” once, for some reason. It’s real weird.
Young Hollywood unleashed
In the same year as that awkward Snow White / Rob Lowe duet, Bob Hope and Lucille Ball scrounged together a bunch of young Hollywood actors (such as Christian Slater and Holly Robinson Peete) and made them perform this musical number as if it were a PTA meeting.
Björk redefines Oscar fashion
Swan dress. SWAN DRESS!
Pilobolus offers shadow puppetry
For those who find Cirque du Soleil and Blue Man Group to be too esoteric, here’s a group of dancers doing funny shadow puppetry. (Sure, it’s not exactly music, but it’s still quite strange.)
Amy Adams sings “Happy Working Song”
Poor Amy Adams was asked to sing this weird little number from Enchanted, and they didn’t even bother to give her a back-up dancer or two. She made it through without breaking down in tears, which is how I would have probably ended my version of this performance.