“Failure is a steppingstone to greatness.”
Those words, spoken by the inimitable Oprah Winfrey, couldn’t be truer in the world of entertainment. Take Walt Disney, fired by the Kansas City Star because his stories “lacked imagination”; or Steven Spielberg, who was twice rejected from the USC School of Cinematic Arts. Following his film acting debut as a bellhop in 1966’s Dead Heat on a Merry-Go-Round, a studio executive took a young Harrison Ford aside and said, “You’ll never make it in this business.”
On Sunday night, 20 actors will vie for Academy Awards. But the road to the Oscars’ stage is paved with rejection—and plenty of regrettable roles.
And so, for the seventh straight year, here are the Oscar nominees’ most embarrassing roles.
Gary Oldman, Tiptoes (2003)
Gary Oldman, character actor par excellence, is all but guaranteed to win the Best Actor Oscar for his utterly convincing portrayal of Winston Churchill in Darkest Hour. And there is no role the 59-year-old Brit is afraid of tackling, from Pontius Pilate to a white Jamaican pimp. This one, however, should have been left alone. Tiptoes stars Matthew McConaughey as a man who is, unbeknownst to his girlfriend (Kate Beckinsale), the only normal-sized member in a family of dwarfs. When she gets pregnant, he feels it best to come clean, since their child may be a dwarf. And so he introduces her to the family—including his twin brother Rolfe, played by Oldman. Since Oldman is 5-foot-9, the dwarf effect was achieved by having him walk around on his knees. Aside from looking terribly unrealistic—and his arms remaining laughably disproportionate—his lower legs are visible in several scenes throughout the film. Yikes.
Margot Robbie, The Elephant Princess (2008)
American audiences were first introduced to the talented Margot Robbie in The Wolf of Wall Street, and she’s equally electrifying as the troubled figure skater Tonya Harding in I, Tonya. Although Robbie is only 27 years young, she didn’t become a star overnight, having appeared in a number of indie films and TV shows in her native Australia—including a four-year stint on the soap opera Neighbours. One of those TV shows was The Elephant Princess, a teen drama trading in gross Orientalism (that also featured Liam Hemsworth). In it, Robbie played Juliet, a white high school girl whose body is taken over by Diva, an evil agent from the fictional Indian land of Manjipoor who, in true Melisandre fashion, is later revealed to be a 600-year-old witch. It’s a problematic role, to say the least. Oh well. Live and learn.
Timothee Chalamet, Clown (2008)
In this writer’s opinion, Timothee Chalamet deserves to win the Best Actor Oscar for so vividly capturing the throes of adolescent agony in Call Me by Your Name. There were, of course, some bumps along the way. With all due respect to his turn as a scalped murder victim on Law & Order, it’s one of his earliest turns in the dreadful 6-minute short Clown that takes the cake. Chalamet plays “Clown Boy,” a young sideshow clown who’s tormented by his menacing clown dad—that is, until he slits the freak’s throat with a straight razor, giving him a taste for murder. Call Me by Your Name this is not. Sorry, Chalamaniacs.
Woody Harrelson, Anger Management (2003)
Woody Harrelson is one of the best character actors alive, and very easily could have earned two Oscar nominations this year, for his turns as a tyrannical colonel in War for the Planet of the Apes and a compassionate cop in Three Billboards Outside Ebbing, Missouri. Heck, he should’ve won an Academy Award for White Men Can’t Jump. But my goodness, was this a mistake. In the Adam Sandler vehicle Anger Management, Harrelson plays Galaxia, a cross-dressing prostitute with a German accent by day, and a Yankee Stadium security guard who goes by “Gary” by night. Galaxia’s cross-dressing is played as a cheap, offensive gag—including a cringe-worthy sequence where, after being picked up under a bridge (and called a “shemale”), she flashes Sandler’s character before cackling with glee.
Saoirse Ronan, I Could Never Be Your Woman (2007)
Amy Heckerling made one of the greatest films of the ‘90s in Clueless, but hasn’t been able to make anything great since. Despite a stellar cast, including Michelle Pfeiffer, Paul Rudd, Tracey Ullman and Saoirse Ronan, this older-woman-falls-for-younger-guy flick is painfully unfunny and awash with rom-com clichés. Ronan plays Pfeiffer’s daughter, who’s almost like a middle-school version of her Lady Bird character—a social pariah navigating the pangs of puberty. The impractical, Dawson’s Creek-esque dialogue, sadly, does her no favors, culminating in an excruciating rendition of Britney Spears’ “Hit Me Baby One More Time” that takes several shots at the princess of pop. For shame!
Daniel Kaluuya, Chatroom (2010)
Following well-received turns in Black Mirror, Kick-Ass 2, and Sicario, the English actor Daniel Kaluuya earned a Best Actor Oscar nod for his riveting performance in Get Out, a film that would take home the Best Picture Oscar if there was any justice in this world. Before he reached the height of his profession, however, Kaluuya appeared in a few less-than-reputable projects. There was Johnny English Reborn, a groan-inducing action-comedy, and Chatroom, an appalling horror film that makes Reborn look like Hitchcock. In the film, Aaron Johnson plays a sadistic teen who cyberbullies other teens into committing suicide. The silly conceit here is that the chatroom chats are acted out in a hotel room. Kaluuya is Mo, a young man who is worried he may be a pedophile due to his attraction to his best mate’s prepubescent sister. Mo is ultimately manipulated into telling his pal his feelings, and is subsequently berated, branded a sexual deviant, and attacked. It’s a messy character in an even messier film, and is sitting at a 9 percent on Rotten Tomatoes.
Meryl Streep, The House of the Spirits (1994)
Steven Spielberg’s The Post is not a very good movie—but Meryl Streep, of course, is excellent as the tortured Post publisher Katherine Graham. She is our greatest living actor, male or female, and has been for the past few decades. But boy, was this a colossal misfire. Based on Isabel Allende’s acclaimed debut novel La casa de los espíritus, it chronicles four generations of the Trueba family before, during and after Pinochet’s military dictatorship in Chile. So yes, Meryl Streep plays a Chilean named Clara del Valle, who is possessed of psychic powers, and she’s never looked more like a deer in headlights than here. It’s not all on Meryl, though, as the entirety of Billie August’s film is a melodramatic mess—a big-budget, star-filled soap opera that resembles a demented parody of Gone with the Wind. The hardest pass.
Mary J. Blige, The 411 (2016)
Mary J. Blige, the R&B diva turned actress, is mesmerizing in Dee Rees’ underappreciated Mudbound, exuding grace and courageous control as the matriarch of a tenant-farming family in rural (and very racist) 1940s Mississippi. For her efforts, she’s received nominations for both Best Supporting Actress and Best Original Song, and should win the latter. Blige has, throughout the course of her outstanding career, been at the center of so many memorable musical moments—but this one she’d probably take back. You’ve seen the clips, the GIFs, the memes, but none of those can do justice to just how amazingly awkward her performance on her talk show The 411 was, wherein she serenaded then-candidate Hillary Clinton with a song about police brutality in America. As the camera cuts from an emoting Blige to Clinton’s concerned/confused face, one can’t help but laugh at the juxtaposition.