The 11 Greatest Times Actors Sang at the Oscars, From Amy Adams to Robin Williams

There was one question on everyone’s lips this awards season: Is Ryan Gosling going to sing “I’m Just Ken” live at the Oscars? The actor, whose turn as Ken in Barbie earned him several nominations this year, has demurred thus far. While perennial winner Billie Eilish has performed her own Oscar-nominated Barbie ballad live at recent award shows, Gosling has preferred to stay silent and seated—thus depriving us of what could very well be a grandiose, unforgettable live performance. Not even his generous Christmas gift to fans, a holiday remix of Ken’s anthemic showstopper with accompanying music video, could abate our thirst for seeing Gosling don the mink live in the flesh, for once and for all.

After months of lead-up, Gosling will grant us our wish: The actor is slated to perform “I’m Just Ken” live during this year’s Academy Awards, which airs March 10. With the song up for Best Original Song—again competing with Eilish’s multiple-award-winning theme—it’s only fair that Gosling gives it the last big push it deserves.

But this brings an interesting, newer question to the table. No shade to Dead Man’s Bones, but we know Gosling for his acting more than anything else. Can an actor really hold his own against professional musicians out there in the Original Song arena? Gosling would be far from the first to do so—and, should “I’m Just Ken” win, he wouldn’t even be the first actor-by-trade to sing the song to Oscars victory.

Below, we look back at the last 30 years of notable Oscar performances from actors pulling double-duty as singers. From a delightful live rendition of “Hakuna Matata” to some charmingly nervous Disney stars, The Daily Beast’s Obsessed will get you toe-tapping down memory lane with these 11 picks.

“Hakuna Matata” from The Lion King (1995, performed by Ernie Sabella and David Alan Grier)

The Lion King was the Barbie of its day, where Best Original Song was concerned. The film was the obvious frontrunner, with three different tracks up for the award. The Academy Awards broadcast featured two of those songs in a medley: “Circle of Life” and, amusingly, “Hakuna Matata.” While I might have swapped that one for the indisputable Best Disney Villain Song Ever “Be Prepared,” watching Ernie Sabella replicate his Pumbaa stylings in real life is a sight worth seeing. This shortened, but no less hilarious, take on the song has Sabella mashing up fart jokes and opera with aplomb, as any Lion King fan would expect. The only downside is that, instead of Nathan Lane joining him as Timon, David Alan Grier subs in—which makes this actor-led performance extra actor-y. But Grier knows to cede the floor to Sabella, helping facilitate a very funny bit. —Allegra Frank

“Blame Canada” from South Park: Bigger, Longer, and Uncut (2000, Robin Williams)

Any awards show enthusiast recalls the hilarity of the 2000 Oscars red carpet. Matt Stone and Trey Parker, co-creators of South Park and first-time nominees, strolled in front of the cameras in familiar dresses: Gwyneth Paltrow’s memorable pink frock, which she wore to the previous year’s ceremony, and Jennifer Lopez’s wildly low-cut green Versace gown from the recent Grammys. Of course professional trolls (non-derogatory, in this case) Stone and Parker would ostentatiously seize their already unexpected moment, and dressing in these dresses to Hollywood’s biggest night was a great way to do it.

But their fashions should not overshadow the reason they were there, which was for writing Best Original Song nominee “Blame Canada.” Mary Kay Bergman sang the anti-nationalist anthem in South Park: Bigger, Longer, and Uncut; unfortunately, she died by suicide months before the Oscars. Robin Williams, of all people, stepped in, leading an array of can-can dancers through a rousing rendition of one of the Oscars’ silliest nominees ever. The dearly departed Williams had many talents, but singing was … much lower on that list. No matter: This is a delightfully goofy performance, as one would expect from both Williams and the South Park boys—who were reportedly tripping balls in the audience. —AF

“I Move On” from Chicago (2003, Catherine Zeta-Jones and Queen Latifah)

Obviously, the 2003 Oscars couldn’t resist including a musical number from Chicago. Catherine Zeta-Jones, Queen Latifah, and a gaggle of burlesque dancers brought the red lights and black sequins to the stage with a rousing performance of “I Move On.” The original song, performed in the film by Zeta-Jones and Reneé Zellweger, played over the movie’s end credits, alongside a sizzle reel of gorgeous choreography. If we’re being honest, this new song was fine, but a weak spot alongside classics from the musical. Pretty much any of the older numbers would have been better, but this one still got the job done—and any excuse to put these actresses on stage is a good one. That said, I still can’t help but wish they’d also gotten to perform “Class”—a duet that now only exists on the film’s soundtrack and in extended editions. —Laura Bradley

“A Kiss at the End of the Rainbow” from A Mighty Wind (2004, Eugene Levy and Catherine O’Hara)

In 2004, the Academy of Motion Picture Arts and Sciences did one of the most marvelously groovy things they’ve ever done when they nominated a song from Christopher Guest’s mockumentary A Mighty Wind for Best Original Song. I’ve long said that most of Guest’s films deserve Oscar recognition, if only because they remain as droll as they were at the time of their initial release. But nominating “A Kiss at the End of the Rainbow” by fictional folk twosome Mitch and Mickey was downright inspired. And it wasn’t just because the song is legitimately good despite being part of a larger punchline, but because it made the genius talents of Catherine O’Hara and Eugene Levy part of Oscar history. During the ceremony, Levy and O’Hara took the stage to perform the song as Mitch and Mickey. In A Mighty Wind, the two former lovebirds have reunited after a tumultuous breakup, and it’s a constant question of how the couple will handle the iconic kiss at the end of the song now that they’re estranged. Just like in the film, O’Hara and Levy planted one on each other once they finished the song for the audience. It was funny, tender, and a celebration of two great comedic talents who deserve endless reverence. Rarely are Oscar performances so wonderful. —Coleman Spilde

“It’s Hard Out Here for a Pimp” from Hustle and Flow (2006, Taraji P. Henson w/ Three Six Mafia)

Before Taraji P. Henson was nominated for her first Oscar—for The Curious Case of Benjamin Button in 2009—and before her musical chops were cruelly snubbed by the Academy this last year for The Color Purple, she joined the ranks of Céline Dion, Barbra Streisand, and Beyoncé: She performed on the Oscars stage. Henson starred in the Oscar-nominated Hustle and Flow, and provided vocals for the original track. The Academy Awards telecast is so rarely invigorated by a hip-hop performance, so it was wild to see the pearl-clutching crowd react to Henson’s performance with Three Six Mafia. —Kevin Fallon

“Happy Working Song” from Enchanted (2008, Amy Adams)

Everyone involved in the Academy should be fired due to the fact that Amy Adams—in 2024!—doesn’t have an Oscar. The fact that she wasn’t even nominated for her ditzy, delightful performance is Enchanted is yet another crime, but I digress. Adams took to the stage to perform a toned-down version of “Happy Working Song” at the 2008 Oscars, killing with her chipper facial expressions alone. No rats, roaches, nor pigeons were needed to make this performance a real treat. —Fletcher Peters

“I See the Light” from Tangled (2011, Zachary Levi and Mandy Moore)

Any duets are sure to please, as is anything Disney—that’s why “I See the Light,” performed by Zachary Levi and Mandy Moore, was a real stunner. Now, “I See the Light” may not be the best song in Tangled. “Mother Knows Best” cannot be topped. But a romantic duet allowed these two hotshot actors to strut their IRL chemistry as they sauntered around the stage, proving why the movie is one of the finest animated rom-coms. As Disney hunts for the stars to replace these two in the upcoming live action remake of Tangled, they’re going to have big shoes (and long hair!) to fill. —FP

“Coming Home” from Country Strong (2011, Gwyneth Paltrow)

Gwyneth Paltrow had eras long before Taylor Swift did. There was her It Girl era. Her Oscar-winner thespian era. Her GOOP era. Her meme-generating DGAF era. In the midst of all this, though, was her singing era. Her song “Cruisin’” with Huey Lewis from Duets was a chart-topping hit. Her guest stint on Glee was all anyone talked about for a full year. And then there was Country Strong, her twangy A Star Is Born-alike in which she sang all her character’s tracks. She performed the original song on several award shows, including the Country Music Awards (where the above video is from, because her Oscars performance has been scrubbed from the internet), and got major props from her A-list pals for daring to do live vocals on entertainment’s biggest night. —KF

“Shallow” from A Star Is Born (2019, Lady Gaga and Bradley Cooper)

How does one even begin to describe this performance? It was talented, brilliant, incredible, amazing, showstopper, spectacular, never the same, totally unique, completely not ever been done before, unafraid to reference or not reference, put it in a blender, shit on it, vomit on it, eat it, give birth to it. First of all, there was Ms. Stefani Joanne Angelina Germanotta in that dress—a gorgeous, billowing, black satin ball gown that ate up half the stage, as Lady Gaga should. There was Bradley Cooper with full-on Jackson Maine scruff. There was the rumored romance that sat between them on stage like a giant elephant, especially as they squeezed onto one tiny piano bench to perform the song’s final notes. It was a perfectly executed celebrity moment, taunting us all with a possibility they’d both already denied eight ways to Oscars Sunday. But most importantly, the song is just an absolute banger. —LB

“I’m Standing With You” from Breakthrough (2020, Chrissy Metz)

Just weeks before the pandemic shut the world down, This Is Us actress Chrissy Metz reminded us to keep our heads held high—and to never walk on fragile frozen water! At the 2020 Oscars ceremony, Metz took the stage to perform “I’m Standing with You,” from her film Breakthrough (which I’ve always thought is the funniest possible title for a film about a child who falls through ice, but that’s neither here nor there). It was odd, considering Breakthrough—a gussied-up Christian movie—was not nominated in a single category other than Best Original Song. Most viewers, including myself, probably wondered what the hell was going on. But Metz would not be deterred! She put her pipes and Diane Warren’s pen to work, singing the song Warren wrote with all the tenacity of a mother trying to save her son from that damned freezing water. If only Miss Metz had warned us about the dangers of delicate ice and the impending novel coronavirus. —CS

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