Join The Community
All working actors in Hollywood have a shared dream: win an Academy Award. Notorious politics aside, to receive the Oscar trophy is to reach the top of the mountain and to be recognized by your peers for all the blood, sweat, and countless tears poured into a project. But having an Oscar doesn't make anyone immune from weird jobs. In fact, you can find many Oscar winners in bizarre roles while watching some of the most unexpected movies.
While the Academy Awards are just an industry award to commemorate yearly achievements, the glitz and glamour of the Oscars ceremonies imbue them with a rare air of ethereal importance. For most of us, it's a chance to fill up our watch lists with all the new best Oscar-winning movies. However, for actors, getting an Oscar feels like being canonized with immortality. You will be remembered forever, is the implicit, unspoken understanding. It's not true of course, but leave it to actors to be dramatic about these things.
Article continues below32. Robert Duvall, in Kicking and Screaming
Year: 2005
Director: Jesse Dylan
It's not that Oscar-winning actor Robert Duvall plays some freak in Kicking and Screaming. His character is a totally ordinary man, one who just happens to be overly competitive even when it comes to pee-wee soccer. What's weird about Robert Duvall is, well, he's Robert Duvall, a committed and commanding presence in a harmless PG-13 comedy where Will Ferrell coaches children's soccer. As the antagonist, Duvall's role is to compel Ferrell to action, to beat his team, and to finally learn to win in the game of life. Duvall excels at doing just that, it's just strange (and pretty funny) to see Tom Hagen yell at kids in soccer jerseys.
31. Natalie Portman, in Lucy in the Sky
Year: 2019
Director: Noah Hawley
In Noah Hawley's Lucy in the Sky, Natalie Portman (who won an Oscar for Black Swan in 2011) plays a NASA astronaut whose personal life unravels when she returns home. The movie is loosely inspired by real-life astronaut and Navy veteran Lisa Nowak, whose romantic entanglements outside her service caught the attention of tabloids circa 2007. Lucy in the Sky avoids sensationalism and presents itself as a serious movie about emotional detachment and disillusionment, but Portman's performance – underpinned by a Southern twang in her voice – makes the movie feel as though it lacks footing on solid ground.
30. Brendan Fraser, in The Passion of Darkly Noon
Year: 1995
Director: Philip Ridley
Brendan Fraser's acting career started out with a number of wacky comedies, like 1992's Encino Man (playing a silly caveman) and 1997's George of the Jungle (playing a silly jungle man). But long before he won the Oscar for the 2022 drama The Whale, Fraser starred in the 1995 psychological horror The Passion of Darkly Noon, playing the grown child of an ultra-conservative religious cult who encounters the outside world for the first time. Fraser shows early promise of his dramatic range in The Passion of Darkly Noon, it's just surreal to see Fraser in a bleak film during his slapstick era.
29. Gwyneth Paltrow, in Shallow Hal
Year: 2001
Director(s): Farrelly Brothers
In a movie "about body positivity" that only the year 2001 could imagine, Shallow Hal stars Jack Black as a sleazy man who chases after women only for their superficial looks. He is hypnotized to see people's inner beauty, which makes him see the morbidly obese Rosemary as a conventionally attractive blonde woman, played by Shakespeare in Love star Gwyneth Paltrow. While Shallow Hal has good intentions, or something close to it, it's just bizarre to see visual gags about a woman's heavyweight with Gwyneth Paltrow in the center of them.
28. Jack Lemmon, in My Fellow Americans
Year: 1996
Director: Peter Segal
Jack Lemmon isn't the only veteran movie star playing a former POTUS in the buddy comedy My Fellow Americans, which also stars James Garner and Dan Aykroyd as other ex-Presidents who together stumble upon a conspiracy. But Lemmon is especially hilarious and weird in it, relishing in his part as a particularly abrasive retired politician who would much rather be anywhere else. Lemmon is a genre icon with some of the best comedy movies like Some Like It Hot and The Apartment under his belt, but his work in My Fellow Americans deserves so much more of the popular vote.
27. Tom Hanks, in Mazes and Monsters
Year: 1982
Director: Steven H. Stern
Tom Hanks, roll for initiative! At the height of the Satanic panic in the 1980s, the popular tabletop game Dungeons & Dragons drew special attention and vitriol from conservative activists who believed the game was teaching youths to practice witchcraft. Inspired by a real-life incident involving a troubled college student, the movie Mazes and Monsters sees a young man – played by Tom Hanks early in his career – lose touch with his reality after developing an obsession with the game. Mazes and Monsters is silly even for made-for-TV standards, but it turns sublime thanks to Hanks' exaggerated crying and lines like "I have spells."
26. Katharine Hepburn, in The Iron Petticoat
Year: 1956
Director: Ralph Thomas
Katharine Hepburn was still in her element throughout the 1950s, earning Oscar nominations for movies like Summertime (1955), The Rainmaker (1956), and Suddenly, Last Summer (1959). But in between those projects, Hepburn starred in what she eventually declared the worst movie of her career. The Iron Petticoat, a war romantic comedy, sees Hepburn play an ice-cold Soviet pilot who gets romantically involved with an American officer (Bob Hope). Though Hepburn was (and is) a giant of the cinema, her cartoonish and unconvincing Russian accent shoots down The Iron Petticoat before it even takes off.
25. Tilda Swinton, in Snowpiercer
Year: 2013
Director: Bong Joon-ho
The bleak, icy future seen in Bong Joon-ho's Snowpiercer is sure to create eccentric characters, but few command your attention like Tilda Swinton's Minister Mason. Existing as a cross between power-hungry political dictators and condescending academic headmasters, Swinton's character exerts the authority of "Wilford," the head of the supertrain that houses the remnants of humanity. Decorated in mink coats that only exaggerate her wretched teeth, Minister Mason is an exhibition of the unpredictable depths Swinton possesses as an actress. It's also a far cry from her Oscar-winning role in Michael Clayton.
24. Ben Kingsley, in Shang-Chi and the Legend of the Ten Rings
Year: 2021
Director: Destin Daniel Cretton
"You'll never see me coming." That's what Ben Kingsley uttered in 2013's Iron Man 3, when he first appeared as the feared terrorist The Mandarin, only to be unmasked as a skittish, out-of-work English actor named Trevor Slattery. In 2021's Shang-Chi and the Legend of the Ten Rings, Kingsley – who received the Oscar for Best Actor for Gandhi (1982) – resurfaced as Trevor, now a "court jester" for the real Mandarin, real name Wenwu (Tony Leung). Kingsley was already great as Trevor before. But in Shang-Chi, a centered and sober Trevor is somehow even weirder.
23. J.K. Simmons, in Red One
Year: 2024
Director: Jake Kasdan
It's jingle barbells all the way for Oscar winner J.K. Simmons. In the 2024 Christmas action-comedy Red One, Simmons steps into the holly jolly boots of a shredded Santa Claus, who gets kidnapped and needs to be rescued by his head of security at the North Pole (played by Dwayne Johnson). Red One is on the naughty list for wasting a thespian like J.K. Simmons, who doesn't seem to be acting so much as just working out with cameras rolling. The joke that the usually rotund Santa Claus is actually cut like lean beef wears thin after only a few minutes.
22. Reese Witherspoon, in Overnight Delivery
Year: 1998
Director: Jason Bloom
In this direct-to-video romantic comedy, Paul Rudd plays a college student who races to intercept a break-up letter paired with some compromising Polaroids of him with another woman to his long-distance girlfriend. That "another woman" is Oscar-winner Reese Witherspoon (who won for the movie Walk the Line in 2006). Witherspoon stars in Overnight Delivery as a stripper who offers to help Rudd's character. Witherspoon was still early in her career at the time, having played sweet girl-next-door types in movies like The Man in the Moon (1991) and Fear (1996). The star continued being America's sweetheart through hits like Cruel Intentions (1999) and Legally Blonde (2001), but the oft-overlooked Overnight Delivery shines a whole different light.
21. Dustin Hoffman, in Meet the Fockers
Year: 2004
Director: Jay Roach
Dustin Hoffman, who won Oscars for the movies Kramer vs. Kramer and Rain Man, gets into Robert De Niro's face in the comedy Meet the Fockers, a direct sequel to Meet the Parents from 2000. Flipping the script of its predecessor, the straight-laced Byrnes family meets the free-spirited bohemian Fockers clan (Dustin Hoffman and Barbra Streisand). Hoffman's Bernie Focker is a former lawyer turned Capoeira-kicking senior who clashes with De Niro throughout the movie. Meet the Fockers is a delirious sequel with outsized actors doing their hardest to be at their most weird.
20. Will Smith, in The Legend of Bagger Vance
Year: 2000
Director: Robert Redford
The Legend of Bagger Vance is a hard movie to describe on paper. At a glance, it's a Depression-era period movie about golf that takes inspiration from Hindu mythology. If your head isn't spinning yet, then let us tell you that Will Smith stars as the titular "Bagger Vance," an angelic stranger who helps the main character (Matt Damon), a haunted World War I veteran, rediscover his groove for the game. After amassing stardom in the late '90s through blockbusters like Bad Boys (1995), Independence Day (1996), and Men in Black (2000), Will Smith playing a "Magical Negro" (as described by Black American critics), seems like a strange step backward for a Hollywood star, radio hit-maker, and as of 2022, an Oscar-winning actor.
19. Sandra Bullock, in Love Potion No. 9
Year: 1992
Director: Dale Launer
It's a classic trope to give an actor greasy hair and thick glasses when you need the audience to know they're an ugly duckling. But the effort feels hilariously forced in Love Potion No. 9, which sees Sandra Bullock (who won an Oscar for the 2009 movie The Blind Side) play a dorky biochemist who, along with the movie's other main character (Tate Donovan), comes across a magical love potion that makes people of the opposite sex fall to their whims. Bullock was just two years shy from her star-making role in Speed, which made everyone succumb to Bullock's allure, no potion necessary.
18. Jack Nicholson, in Mars Attacks!
Year: 1996
Director: Tim Burton
Multi-time Oscar recipient Jack Nicholson was a few decades early in his portrayal of a spineless POTUS eager to sell out American citizens for his own survival. But that just makes his role in Tim Burton's darkly funny Mars Attacks! (aka, one of the best alien movies ever made) timeless. In this ensemble spoof of pulp alien invasion thrillers, Nicholson leads as President James Dale, whose most memorable moment is a desperate plea to save his own rear disguised as a sappy speech about overcoming differences. Though Nicholson's signature sinister aura makes him ideal for the part, you have to wonder how in the world a guy like him got elected in the first place.
17. Al Pacino, in Jack and Jill
Year: 2011
Director: Dennis Dugan
Say hello to his… chocolate blend? Kicking off with an ill-conceived (and totally hilarious) Dunkin Donuts commercial, revered actor Al Pacino – who won Best Actor for the 1993 drama Scent of a Woman – sells out in the 2011 Adam Sandler comedy Jack and Jill. Pacino stars as a fictionalized version of himself, who is roped into appearing in a musical Dunkin ad to hawk "Dunkacinos" and falls head over heels for Sandler's twin sister (played by Sandler wearing a wig). Though Jack and Jill was panned by critics, Al Pacino proves he's the Boston cream of the crop.
16. Denzel Washington, in Gladiator 2
Year: 2024
Director: Ridley Scott
It's a testament to Denzel Washington that he can star in a movie set in ancient Rome, act like a 20th-century New York gangster, and still be the single most commanding character in the whole movie. In Ridley Scott's ostentatious legacy sequel to his hit film Gladiator, Washington plays the villainous Macrinus, an ex-slave and gladiator fight promoter who schemes to take all of Rome for himself. Washington is a trained Shakespearean performer, which implies that none of his choices in playing Macrinus are careless. Though his swagger might feel out of place and out of time, it's a mistake to ever bet against Denzel.
15. Matthew McConaughey, in Serenity
Year: 2019
Director: Steven Knight
The thing with Matthew McConaughey in Serenity is that he's not playing a bizarre character exactly. The actor's renowned handsome ruggedness is perfectly attuned to play a heartbroken fisherman hired by his ex-wife to kill her new husband. But Serenity's offensively awful execution, coupled with its laugh-out-loud story twist, renders anyone watching the film to descend into deafening madness. And not even McConaughey is powerful enough to make it all right, all right, all right. Serenity is so bad it's easy to forget he won an Oscar once, for a slightly better movie in Dallas Buyers Club.
14. Eddie Redmayne, in Jupiter Ascending
Year: 2015
Director(s): Lana Wachowski, Lilly Wachowski
A year after Eddie Redmayne won an Oscar for his performance as Stephen Hawking in The Theory of Everything, the actor became something else entirely: a flamboyant and spoiled villain, with the unintelligible name "Balem Abrasax," in the summer sci-fi Jupiter Ascending. Brandishing a stereotypical "British bad guy" accent and hamming it up in elaborate costumes and eye makeup, Redmayne's Balsamic Abracadabra is like seeing if Prince or David Bowie had infinitely less swag. Though the overzealous overdramatics are obviously intentional choices, it doesn't stop them from feeling overdone.
13. Christoph Waltz, in The Green Hornet
Year: 2011
Director: Michel Gondry
The punchline behind Christoph Waltz's villain "Bloodnofsky" in The Green Hornet is that he's actually a scary villain. He just doesn't know how to be himself. Sadly, this arc is way underdeveloped in Michel Gondry's comedic superhero movie, which sees Seth Rogen and Taiwanese pop star Jay Chou revive the classic pulp superhero Green Hornet – and sidekick Kato – for the 21st century. Waltz's role as an unconfident gangster is a fun swerve from the usual garden variety baddies of other movies, but Waltz just doesn't get enough meat on the bone to make the part sublime. It's a far cry from the more colorful Nazi villain he portrayed in 2009's Inglorious Basterds, which earned him his first Oscar victory.
12. Michael Caine, in The Last Witch Hunter
Year: 2015
Director: Breck Eisner
The Last Witch Hunter just might have the most challenging role in Michael Caine's illustrious career: being subservient to Vin Diesel. In this underrated urban fantasy, Diesel plays the immortal witch hunter Kaulder, a knight who continues waging a secret war against the forces of darkness in the 21st century. Michael Caine plays the first of two "Dolans" – priests tasked with aiding Kaulder. The star's time in the movie is brief, as he is quickly succeeded by a new Dolan, played by Elijah Wood. But it's quite something to see Michael Caine and Vin Diesel share the screen together, playing old chums who go way back.
11. Sam Rockwell, in The Hitchhiker's Guide to the Galaxy
Year: 2005
Director: Garth Jennings
If you met Zooey Deschanel at a party, and she ran off to space with another man, would you still be mad if he was Sam Rockwell? Over a decade before Rockwell won the Oscar for Best Supporting Actor (for Three Billboards Outside Ebbing, Missouri), he played the eccentric alien Zaphrod Beeblebrox in the sci-fi comedy The Hitchhiker's Guide to the Galaxy. Portraying Zaphrod as though a '70s glam rock star had a second job as a used car salesman, Rockwell steals the movie as the fast-talking, slow-thinking, and multi-faced "President of the Galaxy." With another face where his neck should be, Zaphrod is one of Rockwell's most entertaining and simultaneously off-putting roles of his career.
10. Jane Fonda, in Barbarella
Year: 1968
Director: Roger Vadim
In the 1970s, Jane Fonda won two Oscars for the movies Klute (1971) and Coming Home (1978), in addition to her prolific political activism that made her a lot of enemies among the American public. But the '60s saw a more carefree Fonda, with roles in comedies that saw her play up her trophy blonde looks. In the 1968 pulp sci-fi Barbarella, Fonda plays the titular heroine, described as "the most beautiful creature of the future" by the trailer's narrator. Indeed, Barbarella is a sight to behold as a sultry (and often witty) space traveler in this tongue-in-cheek classic. Star Wars it is not, but a whole different Force flows in Barbarella.
9. Ke Huy Quan, in Breathing Fire
Year: 1991
Director(s): Brandon De-Wilde, Lou Kennedy
Ke Huy Quan's Oscar victory for the movie Everything Everywhere All at Once was the defining Cinderella story of the year, his emotional comeback serving as a cosmic justice for the career audiences never saw from him. But rewind the clock to 1991, and you'll find Ke Huy Quan as a teenage butt-kicker in the overlooked martial arts film Breathing Fire. A young Ke Huy Quan (credited as Jonathan Ke Quan) plays one of two teen kickboxers who train to protect their family from a dangerous criminal. Quan's role in Breathing Fire isn't bizarre because he plays an off-kilter weirdo. It's bizarre because Quan is totally locked in as a formidable action lead with boyish good looks, a template later fulfilled by the likes of Channing Tatum and Ryan Gosling. To watch Breathing Fire is to wonder: What could have been?
8. Nicole Kidman, in Destroyer
Year: 2018
Director: Karyn Kusama
In addition to being an Oscar recipient, Nicole Kidman is universally renowned for her outward beauty. She's been the face of luxury brands like Chanel and Balenciaga, and in 2021 was praised by Vogue as a "style icon." But in 2018, Nicole Kidman underwent an extensive transformation to play a world-weary L.A. cop in Karyn Kusama's crime thriller Destroyer. Wholly unrecognizable with a visage as creased as a tattered road map, hair salt-and-peppered, Kidman reveals a completely different side to her craft that few could have ever imagined.
7. Kevin Costner, in Waterworld
Year: 1995
Director: Kevin Reynolds
In the world of Waterworld, climate change has sunk all of planet Earth underwater. Waterworld also sunk Kevin Costner's career, being a wildly expensive box office bomb that diminished Costner's star power until he resurged with one of the best TV shows ever made, Yellowstone. But while the movie itself has a dubious reputation, little is said about Costner's character. A nameless protagonist known only as "The Drifter," Costner is an uninspiring action hero, an eternally-soaked stereotypical swashbuckler or predictable personality. While Costner's acting persona has always implied a sense of detachment, Waterworld just sees him lost at sea.
6. Charlize Theron, in That Thing You Do!
Year: 1996
Director: Tom Hanks
Charlize Theron was just getting started in Hollywood when she landed the part of beautiful Tina in Tom Hanks' That Thing You Do! A far cry from the capable femme fatales she'd later be known to play or her 2003 Oscar-winning role in Monster, Theron's miniscule part in That Thing You Do! sees her as the attention-hungry girlfriend of Guy (Tom Everett Scott), drummer of The Wonders, who dumps him for her dentist just as the band climbs the Billboard charts. More of a comedic bit part than a lasting villainous foil, Theron is predictably radiant but bizarrely glossed over in favor of Liv Tyler.
5. Diane Keaton, in Smother
Year: 2008
Director: Vince Di Meglio
Decades after Diane Keaton won an Oscar for her role in Annie Hall, she became an overbearing mother in Smother. An overlooked comedy that premiered on Lifetime in 2008, Keaton plays an aging mother who moves in with her grown adult son (Dax Shepard) and his wife (Liv Tyler) and becomes a comically intrusive presence in their already delicate relationship. Smother is no one's favorite movie, but Keaton is clearly having a lot of fun being the world's worst greatest mother.
4. Cillian Murphy, in Breakfast on Pluto
Year: 2005
Director: Neil Jordan
For the 2023 movie Oppenheimer, Cillian Murphy won an Oscar for his nuanced performance as physicist Robert J. Oppenheimer – the "Father of the Atomic Bomb." Long before that, though, he caused a few ripples in the understated comedy-drama Breakfast on Pluto. Murphy stars as a transgender woman in 1970s Ireland who searches for her lost mother. Murphy's performance is full of questionable choices, with a particularly clumsy approach to the characters' trans identity. It's not easy to tell when the movie is telling jokes and when it's being real. You almost have to be smart enough to split the atom to know the difference.
3. Robert De Niro, in Brazil
Year: 1985
Director: Terry Gilliam
Robert De Niro never played a superhero in his prolific movie career. But for Terry Gilliam's sci-fi satire Brazil, De Niro makes a fun cameo as a masked vigilante and heating engineer – a "Repair Man," if you will. With the machismo of Superman and the tools of Batman, De Niro swoops in to save the day for a hapless government employee (Jonathan Pryce), whose issues with his air conditioning would be left unresolved otherwise. De Niro's character is a clandestine freelancer who operates off the books, away from the prying eyes of the law. It's a cool little part, a pleasant surprise if you had no clue De Niro was in Brazil when you started it.
2. Emma Stone, in Aloha
Year: 2015
Director: Cameron Crowe
Emma Stone has collected numerous accolades including Oscars and Golden Globes. But the seemingly harmless rom-com Aloha is a movie she'd probably want us all to forget. While Cameron Crowe's film is as offensive as vanilla, its tiny infamy stems from how it features the unmistakably white Emma Stone as a multi-ethnic Air Force pilot, Captain Allison Ng. (There's even a part in where Stone teaches Bradley Cooper how to say "Ng," a common Southeast Asian surname.) While there was nothing wrong with Stone's performance, it became part of a larger conversation about a lack of diversity in Hollywood that questioned the dubious tradition of white actors playing non-white roles.
1. Forest Whitaker, in Ghost Dog: The Way of the Samurai
Year: 1999
Director: Jim Jarmusch
A few years before Forest Whitaker won an Oscar for The Last King of Scotland, he was a philosophizing mob hitman in Jim Jarmusch's off-kilter crime film Ghost Dog: The Way of the Samurai. Existing as a spiritual homage to the 1967 classic Le Samourai, Ghost Dog sees Whitaker play a freelance hitman for the Italian mob. When he's not killing their enemies, he espouses the virtues of the samurai bushido code, quoting the Hagakure like a priest quoting scripture. A playful riff that combines the mafia genre with kung fu and samurai movie conventions, Ghost Dog: The Way of the Samurai walks to the beat of its own boombox.
