Oscars Top 10 Best Song performances ever: Bruce Springsteen, Madonna, Mariah Carey, Whitney Houston …

Numerous Grammy, Tony and Oscar winners have graced the stage on Academy Awards night to perform tunes contending for Best Song. Most of these performances have, at the very least, proven serviceable renditions, though there has been the occasional underwhelming turn. There have also, however, been some truly exceptional Best Song performances, a few downright legendary and others more obscure but just as powerful. (See our top 10 list of worst performance ever.)

This year, John Legend (performing “City of Stars” and “Audition” from “La La Land”); Auli’i Cravalho and Lin Manuel-Miranda (performing “How Far I’ll Go” from “Moana”); Justin Timberlake (performing “Can’t Stop the Feeling” from “Trolls”); and Sting (performing “The Empty Chair” from “Jim: The James Foley Story”) will take to the Oscar stage to sing this year’s nominees. Will any of these acclaimed artists, however, turn in a performance on the same level of these 10 extraordinary past Oscar appearances?

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1. “Streets of Philadelphia” from “Philadelphia” (1993)
Performer: Bruce Springsteen

The 1993 Oscar ceremony was hardly without its share of laugh-out-loud moments as Whoopi Goldberg turned in a remarkably witty and hilarious performance in her first hosting stint. Time stood still, however, as the already-legendary Springsteen took to the stage to perform his “Streets of Philadelphia” from Jonathan Demme‘s “Philadelphia,” the first big-budget film to address HIV/AIDS. Springsteen’s haunting rendition of the song, which so devastatingly captured the pain felt by all too many at the height of the AIDS epidemic, is one of the finest live performances he’s ever delivered. The artist would go on to win the Best Song Oscar that evening, and an additional four Grammy Awards for the tune.

2. “The Way He Makes Me Feel” from “Yentl” (1983)
Performer: Jennifer Holliday

It isn’t always the case that the original performer of a Best Song nominee graces the Oscar stage to belt out his or her signature tune. This year, for instance, we’re seeing Grammy-winner John Legend perform songs originally done by Ryan Gosling and Emma Stone in “La La Land.” In some cases in Oscar history, a new performer has completely botched the recognized song – case in point, Ann Reinking‘s odd rendition of Phil Collins‘ “Against All Odds” from “Against All Odds” (1984). In other instances, however, an artist has been able to match, if not surpass the original performer’s turn, and in no case was that more stunning than Jennifer Holliday’s sublime cover of Barbra Streisand‘s “The Way He Makes Me Feel” from “Yentl.” Streisand’s original version was gorgeous and seemingly impossible to top. Holliday, however, then a hot up-and-comer with Broadway’s “Dreamgirls,” interjected some R&B/soul flavor into the tune and holy cow, did it prove a jaw-dropping success.

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3. “A Kiss at the End of the Rainbow” from “A Mighty Wind” (2003)
Performers: Eugene Levy and Catherine O’Hara

Christopher Guest’s “A Mighty Wind,” the most heartfelt of the filmmaker’s side-splittingly funny mockumentaries, features the characters of Mitch (Eugene Levy) and Mickey (Catherine O’Hara), a former couple that released a bunch of folk music albums in the 1960s until their dramatic breakup – an event that left Mitch emotionally devastated for the rest of his life. Their most famous tune was “A Kiss at the End of the Rainbow” – penned for the film by actors Michael McKean and Annette O’Toole – a lovely song which always ended in a kiss between Mitch and Mickey. In the film’s grand finale, centered on a reunion among ’60s folk artists, the couple performs the tune for the first time in decades, and it’s that long-awaited kiss that proves the picture’s most unforgettable moment. Even Oscar night attendees who hadn’t seen “A Mighty Wind” must’ve been moved by Levy and O’Hara’s sweet and immensely endearing recreation of this moment.

4. “Friend Like Me” from “Aladdin” (1992)
Performer: Nell Carter

A collective sigh of disappointment was shared among Oscar followers and other film fans when it was announced the incomparable Robin Williams, so downright brilliant voicing the Genie in Disney’s “Aladdin,” would not take to the Oscar stage to perform the grand solo number “Friend Like Me.” Little did viewers know how deliriously fun his replacement – the delightful Tony-winner Nell Carter – would be. This splashy, campy, all-around enjoyable take on the tune managed to overshadow performances of fellow Best Original Song nominees “A Whole New World” from “Aladdin” and “I Have Nothing”/”Run to You” from “The Bodyguard” – the latter sung by Natalie Cole, subbing for Whitney Houston.

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5. “Sooner or Later (I Always Get My Man)” from “Dick Tracy” (1990)
Performer: Madonna

Madonna has never been an Oscar favorite. She was overlooked countless times in Best Song, for the likes of “Into the Groove” from “Desperately Seeking Susan” (1985) and “Crazy for You” from “Vision Quest” (1985), to “Live to Tell” from “At Close Range” (1986) and “This Used to Be My Playground” from “A League of Their Own” (1992). In 1990, however, the academy couldn’t resist nominating the legendary Stephen Sondheim‘s “Sooner or Later (I Always Get My Man)” from “Dick Tracy,” which meant having the film’s leading lady at last gracing the Oscar stage to perform an original tune. Her performance was a memorable one to say the least, as Madonna donned an appearance that was a dead-ringer for Marilyn Monroe and delivered a sultry, crowd-pleasing rendition of the Sondheim tune.

6. “Blame Canada” from “South Park: Bigger, Longer and Uncut” (1999)
Performer: Robin Williams

Seven years after Carter stepped into his shoes as the Genie, Williams finally saw an opportunity to perform an original tune when “Blame Canada” from the wonderfully raunchy “South Park: Bigger Longer and Uncut” nabbed a Best Song nomination. Backed by a comparably enthusiastic ensemble, Williams stole the show with an uproarious musical turn, leaps and bounds more memorable than the performance of Phil Collins, that year’s ultimate Best Original Song winner for “You’ll Be in My Heart” from “Tarzan.” The following year, “South Park” took aim at Collins with the episode “Timmy 2000,” in which the artist is portrayed as a villain who carries his Oscar with him everywhere he goes.

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7. “Travelin’ Thru” from “Transamerica” (2005)
Performer: Dolly Parton

Three 6 Mafia‘s “It’s Hard Out Here for a Pimp” from “Hustle & Flow” may have proven victorious in the 2005 Best Song race but it was Dolly Parton’s “Travelin’ Thru,” composed for the Felicity Huffman-headlined “Transamerica” that most charmed the pants off viewers on Oscar night. This terrific top-tapper, written 25 years after Parton’s first Oscar nomination with “9 to 5,” was an irresistible crowd-pleaser that even had three-time Oscar-winner Jack Nicholson clapping along in the audience.

8. “Listen”/”Love You I Do”/”Patience” from “Dreamgirls” (2006)
Performers: Beyonce, Jennifer HudsonAnika Noni Rose and Keith Robinson

While composer Henry Krieger‘s new songs for the long-awaited film adaptation of Broadway’s “Dreamgirls” could not quite match the gargantuan strength of tunes like “I Am Telling You I’m Not Going” and “I Am Changing” from the original stage production, there was still something awfully special about the medley of new tunes showcased on Oscar night in 2006. Enthusiastically performed by the film’s talented young stars, this trio of tunes proved plenty memorable, even if all ended up falling to Melissa Etheridge‘s “I Need to Wake Up,” from “An Inconvenient Truth,” for the Best Original Song prize.

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9. “Belle”/”Be Our Guest” from “Beauty and the Beast” (1991)
Performers: Paige O’Hara, Richard White and Jerry Orbach

Disney productions have proven hit-or-miss when it’s come to Best Song performances at the Oscars, in large part on account of how they’re choreographed. At the 1989 ceremony, for instance, Paula Abdul‘s spastic, headache-inducing direction all but sank the recognized tunes from “The Little Mermaid.” Two years later, however, with Oscar veteran Debbie Allen back as ceremony choreographer, the presentation was vastly superior for two of the nominated songs from Best Picture nominee “Beauty and the Beast” – “Belle” and “Be Our Guest,” performed back-to-back. With O’Hara, White and Broadway legend Orbach, all performers from the film, taking the stage, the production captured the magic of “Beauty and the Beast” in a way that the Oscars’ “Little Mermaid” tribute certainly did not.

10. “When You Believe” from “The Prince of Egypt” (1998)
Performers: Mariah Carey and Whitney Houston

Carey and the late Houston may have a combined 11 Grammy Awards but remarkably, on only one occasion have these pop divas performed a Best Song nominee at the Oscars. That single performance happened to be a dual effort, as Carey and Houston teamed up to belt their hit “When You Believe” from “The Prince of Egypt.” While not among the most memorable tunes from either of their packed discographies, “When You Believe” was still a plenty notable effort and worthwhile if only for the opportunity to see these beloved artists finally collaborate.

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