Oscar Nominees’ Most Embarrassing Roles: Casey Affleck’s Sexpert, Asian Emma Stone, and More

Before they were the toast of Tinseltown, this year’s Oscar-nominated stars appeared in some, shall we say, less-than-stellar fare.

Photo Illustration by The Daily Beast

On Sunday night, Hollywood’s elite will gather at the Dolby Theatre to toast this year’s chosen ones at the 89th annual Academy Awards. There will be laughter, tears, and a deluge of jokes aimed at our remarkably thin-skinned president. There will be Jimmy Kimmel, who, as the night’s emcee, will rib his pseudo-nemesis Matt Damon for turning down Casey Affleck’s role in Manchester by the Sea. And there will be the races themselves. Will the silly La La Land backlash cost it Best Picture against Moonlight? Will the incomparable Viola Davis win her first Oscar? (She better.) And will the younger Affleck’s past come back to haunt him?

While these actors have reached the height of their profession, it’s good to remember where you came from. And so, in honor of the upcoming Oscars, here is our seventh annual edition of ‘Oscar Nominees’ Most Embarrassing Roles,’ highlighting the jobs that this year’s crop of nominees would rather have deleted from their IMDb pages. For all the struggling actors out there, don’t worry: it gets better. Casey AffleckTom Myers, American Pie movies

Before he became a respected Hollywood actor with the one-two punch of Gone Baby Gone and The Assassination of Jesse James by the Coward Robert Ford, two-time Oscar nominee Casey Affleck (Manchester by the Sea) went through a period where he navigated some pretty regrettable teen-targeting fare in the late-‘90s and early aughts, from the Heather Graham-starrer Committed to the dreadful psychological thriller Soul Survivors. But it’s his appearance as Tom Myers, the “wise” older brother to Thomas Ian Nicholas’s Kevin in the first two American Pie movies, that stands out. In the first film, Tom passes along a mysterious—and utterly ridiculous—sex manual to his virginal little bro, and in the second, advises him that renting a summer house with his buds will be a transformative experience like no other. Hopefully Ben Affleck gave better advice.

Nicole KidmanDevlin Adams, Just Go with It

Nicole Kidman has evolved into a very excellent, very blonde actress. Her performance as the homicidal weather lady Suzanne Maretto in Gus Van Sant’s To Die For remains, in my opinion, one of the better female film turns of the ‘90s. So it came as a bit of a shock when Kidman, this year nominated for her fourth Oscar for Lion, appeared in one of Adam Sandler’s paid vacations. In the Hawaii-set Just Go with It, she plays Devlin Adams, the frenemy of Jennifer Aniston’s character who appears to have it all together but is, like Aniston’s character, a total mess. The usually gripping Kidman sticks out like a sore thumb in this broad Sandler comedy, struggling to hit the (admittedly lame) comedic notes. Hopefully she got a nice tan and some piña coladas out of it.

Ryan Gosling Jamie Leary, Are You Afraid of the Dark?

Ryan Gosling’s performance as Daniel Balint, a Jewish neo-Nazi struggling with his identity in 2001’s The Believer, established the young Canadian as one of the finest actors of his generation. His transcendent turn as a crack-addicted inner city teacher in Half Nelson sealed it. But before all that, Gosling was an accomplished child actor, first appearing in Disney Channel’s Mickey Mouse Club with Justin Timberlake, Britney Spears, and Christina Aguilera, and then on a number of assorted other children’s television shows. In this, the third episode of the fifth season of the kids’ horror-anthology series Are You Afraid of the Dark?, Gosling plays Jamie Leary, a young death-obsessed kid who happens upon a radio station that transports its listeners to the afterlife. Gosling’s over-acting is especially hilarious given how fine-tuned his performances are today—like his Oscar-nominated soft shoe turn in La La Land.

Michelle WilliamsHobie’s Groupie, Baywatch

After making a name for herself as Jen Lindley, the fetching “new girl in school” on WB’s Dawson’s Creek, Michelle Williams has gone on to become one of the most lauded actresses around, receiving a fourth Oscar nomination for her turn as a grieving widow in Manchester by the Sea. Before achieving screen stardom, Williams appeared in a number of bit parts on film and television, including: as the younger version of Natasha Henstridge’s seductive alien in Species, a high schooler on the run from Michael Myers in Halloween H20, and tiny roles on the TV series Step by Step and Home Improvement. One of Williams’s first screen performances came on an episode of Baywatch in 1994, where the then 13-year-old played a random beach groupie (the character’s name is literally listed as ‘Hobie’s Groupie’) who flirts with Hobie Buchannon, the son of Baywatch honcho Mitch Buchannon, played by David Hasselhoff.

Andrew GarfieldVarious Roles, Swinging

As a struggling actor, Andrew Garfield lived in a house in Hollywood with Eddie Redmayne and Jamie Dornan—just three incredibly well-coiffed gents from across the pond trying to make it. The Social Network and a couple of Spider-Man movies later, and Garfield, like Redmayne and Dornan, has achieved coveted leading man status. He’s received his first Oscar nod this year for the World War II drama Hacksaw Ridge, but before he was dodging bullets and the wrath of Mel Gibson, the lanky Brit was dodging a predatory art teacher on the U.K. TV series Swinging. The show, a series of strange sketches concerning sex, featured Garfield as a secondary school student whose art teacher constantly harasses him, attempting to ply the youth with sex and cocaine. It’s pretty painful to watch.

Octavia SpencerMadame Nora, Dinner for Schmucks

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Octavia Spencer is no overnight sensation. The journeywoman actress was forced to appear in dozens and dozens of bit parts en route to her first well-deserved Oscar win as Minny, the fiery, no-nonsense maid, in The Help. Spencer, who’s up for her second Best Supporting Actress turn for Hidden Figures, spent the first decade of her career weathering roles like ‘Neighbor in Alley’ in S.W.A.T. or ‘Big Customer’ in Beauty Shop. Her most unfortunate role, however, was the one right before the big Minny breakthrough—in 2010’s atrocious comedy Dinner For Schmucks, opposite Paul Rudd and Steve Carell. In the film, about sadistic rich people who are rewarded for bringing the biggest moron to a dinner, Spencer plays ‘Madame Nora’—a woman who claims to be able to channel the spirits of dead animals (think: Whoopi Goldberg’s character in Ghost gone even more haywire). The scene where she channels a dead lobster is… something else.

Michael ShannonFloyd Poteet, Bad Boys II

These days, if you know a film has Michael Shannon in it, you know you’re at least getting your money’s worth. He is flat-out one of the best actors alive; a performer whose onscreen intensity is unsurpassed. But that wasn’t always the case. Before his breakout turn as a paranoid Gulf War veteran in Bug, Shannon was tasked with tedious roles in crap films like Pearl Harbor and Kangaroo Jack. One of the most bizarre was the role of Floyd Poteet, a backwater Ku Klux Klansman who’s also involved in a massive Miami drug-smuggling ring. After being collared, the racist prick is made to help Will Smith and Martin Lawrence take the ecstasy kingpins down.

Emma StoneAllison Ng, Aloha

Hollywood has an Asian problem. From Mickey Rooney portraying the caricature I.Y. Yunioshi in Breakfast at Tiffany’s to Scarlett Johansson’s whitewashed turn in the upcoming Ghost in the Shell, there is an embarrassing reluctance on the industry’s part of casting Asian actors to play Asian characters—even though Asia accounts for a disproportionate percentage of a film’s box office gross. One of the sillier examples was Cameron Crowe’s disasterpiece Aloha, which starred Emma Stone (!) as the part-Asian Allison Ng. There was, understandably, a huge backlash, and Stone, who is by all accounts a lovely young woman—and excellent as an aspiring actress in La La Land—apologized for the gaffe, stating: “I’ve learned on a macro level about the insane history of whitewashing in Hollywood and how prevalent the problem truly is. It’s ignited a conversation that’s very important.”

Denzel WashingtonLincoln Rhyme, The Bone Collector

Just as Tom Cruise is Hollywood’s best movie runner, Denzel Washington is its best walker. It’s more of a stroll, really. And fuck, does it look cool. The man glides down city sidewalks like he owns not just the street, but the whole damn county. So why the hell would you confine Denzel to a hospital bed? That’s what happened in 1999’s The Bone Collector, a godawful thriller starring Denzel as Lincoln Rhyme (what a name), a tetraplegic forensics expert advising a rookie cop (Angelina Jolie) on the hunt for a serial killer from his hospital bed. Denzel spends the whole movie in bed on the phone with Jolie, which sounds like a pretty sweet gig, but doesn’t make for compelling cinema.

Viggo MortensenLucifer, The Prophecy

There have been some pretty ridiculous movie devils. Who can forget overactin’ Al Pacino yelling that God is AN ABSENTEE LANDLORD! in The Devil’s Advocate, or Harvey Keitel’s withering Satan in Little Nicky, or even Arnold Schwarzenegger shouting at Gabriel Byrne’s rapey devil, “You’re a fucking choir boy compared to me!” in End of Days. And look, Viggo Mortensen is one of the best in the biz, and is every bit deserving of his Best Actor Oscar nod for Captain Fantastic—hell, he should have won for Eastern Promises—but his hissing turn as Lucifer in the absurd 1995 flick The Prophecy is over-the-top hilarious (in a so-bad-it’s-fun way).