“Music’s biggest night” already happened, but that never stops the Oscars from staging its own miniature musical extravaganza, with Lady Gaga, Jennifer Hudson, and Bette Midler all set to perform at Sunday’s ceremony. The Academy has always included music in some capacity, albeit to sometimes bleak results (hi, Rob Lowe and Snow White). But there are plenty of highlights from Oscars’ past that deserve repeat viewings. Whether any of the performers from this year’s show will make the “best of” list remains to be seen.
Ahead, in no particular order, is a rundown of the best and boldest musical performances from Academy Awards past.
“Blame Canada” — Robin Williams (2000)
We kick things off on a comedic note, with the pièce de résistance of Trey Parker and Matt Stone’s epic animated musical South Park: Bigger, Longer, Uncut. The late, great Robin Williams steps in to perform Sheila Broflovski’s Canadian shame anthem “Blame Canada,” with an assist from some Rockette-inspired Mounties. Sadly, “Canada” lost out on the Best Original Song Oscar that year to the schmaltzy Phil Collins track “You’ll Be in My Heart” from Tarzan.
Three 6 Mafia — “It’s Hard Out Here for a Pimp” (2006)
The most pleasantly unexpected Oscars performance in history goes to the legendary Memphis hip-hop trio, and their rendition of “It’s Hard Out Here for a Pimp,” from the film Hustle & Flow. Their rendition for the Academy featured a full trap house on stage, along with Flow star Taraji P. Henson singing the hook. The only thing more enjoyable than watching Three 6 bounce around the Kodak Theatre stage was watching them accept the award for Best Original Song from Queen Latifah. “That’s how you accept an Oscar,” said host John Stewart.
“Til it Happens to You” — Lady Gaga (2016)
This powerful, poignant ode to sexual assault survivors — made for the documentary The Hunting Ground, about campus rape — received an even more powerful and poignant live version at the 2016 Academy Awards, with Lady Gaga singing and playing piano flanked by individuals who had experienced sexual abuse.
“Last Dance” — Donna Summer (1979)
The only thing missing from this Donna Summer performance of the Oscar-winning single “Last Dance” — off the soundtrack to the 1978 flick Thank God It’s Friday — is a giant disco ball.
“Skyfall” — Adele
For decades, the James Bond theme has served as a sort of rite of passage for both established and up-and-coming artists. Adele was already a superstar by the time producers recruited her for eventual Best Original Song winner “Skyfall,” with the British artist and her booming mezzo-soprano delivering one of the best 007-inspired tracks since the series’ inception. Her live take at the Oscars might be better than the studio version.
“Goldfinger” — Shirley Bassey (2013)
Speaking of Bond, for the series’ 60th anniversary, Dame Shirley Bassey showed up to sing what is arguably the series best theme. Listening to Bassey hit that final note is better than the world’s greatest vodka martini.
“My Heart Will Go On” — Celine Dion (1998)
The Oscar song to end all Oscar songs, Celine Dion’s multi-platinum, chart-topping ode to Jack and Rose from James Cameron’s Titanic was a shoo-in for Best Original Song at the 1998 ceremony, just one of the 11 trophies the film took home that night. Dion’s performance — complete with string section — was the perfect cap to a track that had dominated radio all year.
“Happy” — Pharrell Williams (2014)
The very energetic backup dancers, Lupita N’yongo and Amy Adams dancing, Pharrell’s hat — honestly, what’s not to love about this Academy Awards performance of the producer-rapper-singer’s global hit from the Despicable Me 2 soundtrack? Even Meryl Streep gets into it.
“Glory” — Common and John Legend (2015)
From director Ava DuVernay’s enthralling 2014 film Selma, “Glory” served as a compelling tribute to the Civil Rights movement and those who marched from Selma to Montgomery, Ala. in support of voting rights. For the Oscars, Common and Legend performed the track in front of a recreation of the famed Edmund Pettis Bridge. “This bridge was once a landmark for a divided nation,” said Common, during his and Legend’s acceptance speech for Best Original Song, “but now it’s a symbol for change.”
“Streets of Philadelphia” — Bruce Springsteen (1994)
He may hail from Jersey, but the Boss put in decade-best work with this mournful single tied to Jonathan Demme’s Philadelphia. The song became a critical and commercial hit, with Springsteen winning Best Original Song after singing it at the ‘94 ceremony.
“Mystery of Love” — Sufjan Stevens (2018)
This toned-down (for him, at least) live performance by the multi-instrumentalist comes complete with an Italian museum backdrop, a pink-and-black striped suit, and St. Vincent on guitar. One listen and you’ll be weeping like poor Elio.
“Shaft” — Isaac Hayes (1972)
Los Angeles’ hottest club in 1972 was Isaac Hayes’ absolutely bonkers Academy Awards performance of the Shaft theme song, complete with dancers on fire escapes, a rolling organ, and the man himself in chain mail. Forget an Oscars monologue, just air this performance to open the show.
“When You Believe” — Mariah Carey and Whitney Houston (1999)
Two of the greatest singers in history joined forces for this gorgeous ballad from the underrated animated flick Prince of Egypt.
“Endless Love” — Diana Ross and Lionel Richie (1982)
Another legendary duet, this time from former Motown stars Lionel Ritchie and Diana Ross. Though the simple and elegant “Endless Love,” from the movie of the same name, missed out on the Best Original Song that year, it did top the Hot 100.
“This Is Me” — Keala Settle (2018)
Even more impressive than Greatest Showman star Keala Settle belting out a goosebump-inducing version of “This is Me” at the Academy Awards? The fact that she had a stroke a week before the performance.
“Everything is Awesome” — Tegan and Sara, the Lonely Island, Mark Mothersbaugh (2015)
It is stupidly obvious to say that everything is awesome about this performance of the lead single from The Lego Movie, but, well, there’s really no other way to describe it. This thing features Tegan and Sara, the Lonely Island, and Oprah receiving an Oscar made out of LEGOs. Beat that, non-animated movies.
Dreamgirls medley — Beyonce, Jennifer Hudson, Anika Noni Rose (2007)
Beyoncé has had so many career-defining moments over the last decade that it’s easy to forget how good these performances of “Love You, I Do” with an equally stunning Jennifer Hudson, and “Listen” are.
“Can You Feel the Love Tonight?” — Elton John (1995)
A booming live version of the Elton John and Tim Rice ballad about the young lions Simba and Nala, the track serves as one of the many highlights from the 1994 Lion King soundtrack, going on to win that year’s Best Original Song Oscar.
“Sooner or Later” — Madonna (1991)
Madonna turned the Academy Awards into a cabaret via this Stephen Sondeheim-penned song from Dick Tracy, which also co-starred the “Like a Prayer” singer. If only her recent awards show appearances were as gripping.
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