Winning an Oscar is supposed to be the pinnacle, right? The ultimate stamp of approval, the golden ticket to prestige projects and paychecks. But how could it ever be that simple? There’s a long history of actors who, after basking in the glow of their Academy Award moment, have suddenly found themselves struggling to land roles, battling weird industry backlash, or – if they happen to be a woman – being deemed “too difficult” overnight.
Some just call it the Oscar curse, because Hollywood loves to anoint a star, but it also loves to tear one down. Having said that, there’s a rare breed of actors who not only win an Oscar but do it again. And again. So who are these titans of the Academy, the actors who didn’t just win but kept winning?
25. Elizabeth Taylor
Elizabeth Taylor’s love life was famously dramatic, but, as she herself described it, one small gold man entered in 1961 and never left – her first Oscar. After three consecutive nominations for Raintree County (1957), Cat on a Hot Tin Roof (1958), and Suddenly, Last Summer (1959), Taylor finally won Best Actress for Butterfield 8. But the moment was bittersweet. Still mourning her husband Mike Todd’s death, she had also barely survived a near-fatal bout of pneumonia just weeks before.
By the time she won again in 1967 for Who’s Afraid of Virginia Woolf?, Taylor was in much better spirits. Though she skipped the ceremony, the win was monumental. Beyond her two Oscars, Taylor’s legacy extended to humanitarian work, earning her the Jean Hersholt Humanitarian Award in 1992.
24. Jodie Foster
Jodie Foster had long been an Oscar favorite, and her 2024 nomination for Nyad last year marked a surprising return – her first nod in nearly 30 years. A two-time Academy Award winner, Foster had been nominated in four of the six decades she worked in the industry, an incredible feat for any actor.
Her Oscar journey began in 1977 at just 15, earning a Best Supporting Actress nomination for Taxi Driver. She claimed her first win in 1989 for The Accused, delivering a powerful performance as a rape survivor. Just a few years later, she secured her second Oscar for The Silence of the Lambs. Her last nomination before Nyad came in 1995 for Nel.
With Nyad, however, her nomination made history for LGBTQ representation, as she and Colman Domingo became the first openly LGBTQ actors nominated for playing LGBTQ roles.
23. Gary Cooper
Gary Cooper was Hollywood’s ultimate leading man – effortless and natural. Over three decades, he built a career, earning five Oscar nominations, two wins, and an Honorary Award in 1961.
His first Oscar came for Sergeant York (1941), where he played a humble war hero torn between faith and duty. A year later, he scored another nomination as baseball icon Lou Gehrig in The Pride of the Yankees (1942).
It was, however, High Noon (1952) that sealed his legacy. As Marshal Will Kane, standing alone against danger, Cooper won his second Oscar. He wasn’t flashy – just real. And that’s what made him great.
22. Fredric March
Fredric March was one of Hollywood’s greatest, yet often overlooked, actors. He first worked in banking before a health scare pushed him toward acting – a decision that led to a legendary career.
March won two Academy Awards, first for his dual role in Dr. Jekyll and Mr. Hyde (1931), making him one of the rare actors to win for a horror film, and again for The Best Years of Our Lives (1946), where he played a struggling WWII veteran. In 1947, he made history as the only actor to win an Oscar and a Tony in the same year.
Unlike many stars of his time, March freelanced, choosing roles across genres – drama (Les Misérables, Inherit the Wind), romance (A Star Is Born), and comedy (I Married a Witch).
21. Michael Caine
Michael Caine doesn’t need the Oscars, he’s been around long enough. But awards don’t hurt, do they? And he already has a few. His first Oscar nod came in 1967 for Alfie, followed by another in 1973 for Sleuth. In total, he’s been nominated six times, winning twice for Best Supporting Actor.
Caine’s first win, for Hannah and Her Sisters, came while he was off filming Jaws: The Revenge – a rather funny example of the highs and lows of his career. The second came for his role as Dr. Larch in The Cider House Rules (1999).
The nomination closest to his heart, however, was for The Quiet American (2002), where Caine played a lonely journalist in Saigon. He thought it was his best shot at a Best Actor win, but the competition was fierce that year, with Nicolas Cage, Adrien Brody, Daniel Day-Lewis, and Jack Nicholson all in the running.
After the ceremony, Nicholson invited the nominees for drinks, and they got so hammered they couldn’t remember their speeches. When Brody won, Caine was genuinely happy for him – though Halle Berry might have felt differently after his infamous kiss.
20. Maggie Smith
Maggie Smith was such a British institution that it’s easy to forget Hollywood claimed her, too. Over nearly seven decades, she racked up six Oscar nominations – four for Best Supporting Actress and two for Best Lead Actress – spanning from the 1960s to the 2000s, by which point Harry Potter had made her a household name.
Smith’s first nod came in 1966 for Othello, but it was The Prime of Miss Jean Brodie (1969) that won her Best Actress. As an unconventional teacher whose ideas put her at odds with the system – though true to form, she skipped the ceremony to do a play in London.
She kept racking up nominations with Travels with My Aunt (1972), A Room with a View (1985), and Gosford Park (2001). It was, however, 1978’s California Suite, a Neil Simon comedy, that earned her a second Oscar. Smith rarely played the Hollywood game, but her talent spoke for itself.
19. Jessica Lange
Jessica Lange has been in the game for 40 years. Despite two Oscars and an impressive career in film and TV, she still feels somewhat underrated. She won her first Oscar for Tootsie (1982), playing soap star Julie Nichols, who finds herself confused by Dustin Hoffman’s disguised alter ego. That same year, she delivered a memorable performance in Frances, playing the brilliant but troubled 1930s actress Frances Farmer – earning a Best Actress nomination.
Lange smoldered in The Postman Always Rings Twice (1981), starring opposite Jack Nicholson as the restless, doomed Cora Smith. Her second Oscar, however, came with Blue Sky (1994), where she played a seemingly flighty military wife. Sensual, defiant, and compelling – Lange has always been more than just a pretty face.
18. Anthony Hopkins
Just a few years ago, Anthony Hopkins made Oscar history, winning Best Actor for The Father at 83, making him the oldest acting winner ever. But the moment itself was anything but triumphant – he wasn’t even there to accept. Instead, presenter Joaquin Phoenix awkwardly accepted the award on Hopkins’ behalf.
In The Father, he played an aging man struggling with dementia, a role that had already won accolades for stage actors before him. This was Hopkins’ second Oscar, coming nearly three decades after his performance as Hannibal Lecter in The Silence of the Lambs (1991), a role that became iconic in film history. Over his career, however, he earned six nominations, for The Two Popes, Nixon, and Amistad.
17. Tom Hanks
A Spielberg favorite, Tom Hanks’ Oscar journey has been a mix of Ws and near-misses, with six nominations and two wins. Throughout the ‘90s, Hanks was an Oscar darling, winning back-to-back Best Actor trophies for Philadelphia (1993) and Forrest Gump (1994), a feat matched by a few. (Later on this list).
A few years later, he earned another nomination for Saving Private Ryan, and by 2001, he seemed poised for a third win with Cast Away. That, however, did not happen, and he is still to win his third. Even when he didn’t take home the gold though, his roles came to define their eras. Few actors have the warmth, humor, and depth as he does – he’s basically America’s dad.
16. Dustin Hoffman
Dustin Hoffman has seven nominations, two wins, and a career packed with some pretty great performances. His Oscar journey started with The Graduate (1967), where he played the awkward, lovestruck Benjamin Braddock. That role put him on Hollywood’s radar, and nominations kept rolling in – Midnight Cowboy (1969), Lenny (1974), Tootsie (1982), and Wag the Dog (1997).
Hoffman’s Kramer vs. Kramer (1979) win was huge, also his first, going up against legends like Al Pacino and Jack Lemmon. 11 years later, he would win again for Rain Man (1988). He hasn’t won since, but does he really need to? Hoffman may not have Meryl Streep’s nomination count or Daniel Day-Lewis’s win ratio, but when it comes to acting that feels real, few can touch him.
15. Jane Fonda
Jane Fonda may have been born into Hollywood royalty, but her two Oscars, seven nominations, and a lifetime of activism are emblematic of a person who has kept evolving. Daughter of screen legend Henry Fonda, Jane found her way to acting after a charity performance with her dad.
She briefly attended Vassar, studied art in Paris, then returned to the U.S. to train with acting legend Lee Strasberg. Her film debut came with Tall Story (1960), and a decade later, she landed her first Oscar nomination for They Shoot Horses, Don’t They? (1969).
Two years later, she won Best Actress for Klute (1971), playing the now-iconic Bree Daniels. She won again for Coming Home (1978), plastering her reputation as one of Hollywood’s most powerful leading women.
Off-screen, Fonda became just as famous for her activism. Outspoken against the Vietnam War, she visited Hanoi in 1972, a trip that led to the infamous “Hanoi Jane” controversy. Decades later, she was still on the front lines – getting arrested in Washington, D.C. during climate protests in 2019, all while flashing a grin.
14. Cate Blanchett
Cate Blanchett is one of the most gifted actors of her generation. From her early days in independent films like Oscar and Lucinda (1997) to her star-making turn as Elizabeth I in Shekhar Kapur’s Elizabeth (1998), Blanchett’s talent was evident from the start. She earned her first Oscar nomination for the role and has since built a filmography many actors can only dream of.
Her first Academy Award win came for portraying another Oscar winner – Katharine Hepburn – in Martin Scorsese’s The Aviator (2004). Her second Oscar win, for Blue Jasmine (2013), would only confirm what many had initially presumed – that she is one of the most powerful performers of her time.
13. Robert De Niro
Robert De Niro’s first Oscar win came for The Godfather Part II (1974), where he played a young Vito Corleone, making history as the first actor to win an Academy Award for playing the same character as a previous winner (Marlon Brando).
Two years later, he earned his first Best Actor nomination for Scorcese’s Taxi Driver (1976). He followed that with another nod for The Deer Hunter (1978), however, losing out to Jon Voight.
De Niro would finally get back to winning ways with Raging Bull (1980), where his transformation into boxer Jake LaMotta – gaining 60 pounds for the role – secured him his second Oscar. He kept returning with nominations for Awakenings (1990) and Cape Fear (1991) but lost both times.
After a 21-year gap, he earned a Best Supporting Actor nod for Silver Linings Playbook (2012), and in 2019, The Irishman brought him his first Best Picture nomination as a producer. He is yet to win again, but it’s De Niro, so you never know.
12. Jack Lemmon
One of Hollywood’s greatest dramedy actors, Jack Lemmon was no stranger to the Oscars, but his 1973 Best Actor win for Save the Tiger felt especially sweet. Having already won Best Supporting Actor for Mister Roberts (1955) previously, Lemmon had endured three Best Actor losses – for Some Like It Hot (1959), The Apartment (1960), and Days of Wine and Roses (1962). But after an 11-year dry spell, he finally got his due.
In Save the Tiger, Lemmon played Harry Stoner, a desperate businessman on the brink. His competition was intense – Marlon Brando (Last Tango in Paris), Al Pacino (Serpico), Jack Nicholson (The Last Detail), and Robert Redford (The Sting). But Lemmon had history on his side. The Academy had been favoring veteran actors, and with Save the Tiger earning other major nominations (Best Supporting Actor, Best Original Screenplay), he had momentum.
After accepting his Oscar, Lemmon quipped, “I had a speech prepared—in 1959.” Though he’d earn two more nominations (The China Syndrome and Missing), Save the Tiger would be his final Oscar win.
11. Marlon Brando
Marlon Brando’s relationship with the Oscars was as dramatic as his acting performances. He first won Best Actor for On the Waterfront (1954) but later called it “silly.” Nearly 20 years later, he was back in contention for his as Vito Corleone in The Godfather (1972). His win was expected, but what happened next wasn’t.
Brando refused the Oscar. Instead, he sent activist Sacheen Littlefeather to the stage, where she declined the award and spoke about Hollywood’s mistreatment of Native Americans. The audience reacted with a mix of applause and boos.
Brando had never cared much for awards. By 1973, he was more focused on activism than acting. He never returned to the Oscars. Though nominated again for Last Tango in Paris (1973) and A Dry White Season (1989), he never won another Academy.
10. Denzel Washington
Denzel Washington has been nominated for an Academy Award ten times – more than any other Black actor. Washington’s Oscar journey began with Cry Freedom (1987), earning his first nomination for Best Supporting Actor.
He won in that category two years later for Glory (1989). The ‘90s would bring more flowers, with a Best Actor nod for Malcolm X (1992) and another for The Hurricane (1999). But it was Training Day (2001) that finally won him the Best Actor award, making him only the second Black actor to achieve that honor.
Since then, Washington has racked up nominations for Flight (2012), Fences (2016), Roman J. Israel, Esq. (2017), and The Tragedy of Macbeth (2021). He even received a Best Picture nomination as a producer for Fences.
9. Spencer Tracy
Plenty of actors have taken home multiple trophies, but winning in consecutive years? Almost impossible. Only two actors have ever pulled it off in the Best Actor category – Spencer Tracy and Tom Hanks – both decades apart.
Tracy’s first Oscar came in Captains Courageous (1937), playing the kindhearted fisherman Manuel. A year later, he won again as Father Flanagan in Boys Town (1938), marking the first time an actor won for playing a real person still alive at the time. Both films also saw him in mentor roles, a fitting parallel.
Tracy’s versatility kept him in the Academy’s sights for decades, earning nominations for San Francisco (1936), Father of the Bride (1950), Bad Day at Black Rock (1955), The Old Man and the Sea (1958), Inherit the Wind (1960), Judgment at Nuremberg (1961), and a posthumous nod for Guess Who’s Coming to Dinner (1967). His acting was pure instinct – natural, subtle, and human, with Hollywood legends from Katharine Hepburn to Clark Gable calling him the best.
8. Bette Davis
Bette Davis racked up 10 Oscar nominations – all in the Best Actress category – putting her in the rarefied company of Meryl Streep and Katharine Hepburn. She won twice. First for Dangerous (1935) and then Jezebel (1938), though ironically, these are among her less celebrated films.
The more frequently remembered films came after, with nominations for Dark Victory (1939), The Letter (1940), The Little Foxes (1941), Now, Voyager (1942), Mr. Skeffington (1944), All About Eve (1950), The Star (1952), and Whatever Happened to Baby Jane? (1962).
Davis made a career out of playing complex, often unlikeable women, taking on roles that others might have shied away from. Even as her film career waned, Davis found success on TV, winning an Emmy for Strangers: The Story of a Mother and Daughter (1979). Fearless, and always working – who else but Bette Davis would take out a Variety ad essentially advertising herself for hire? A legend, through and through.
7. Walter Brennan
Walter Brennan might not be a household name today, but his Oscar record is nearly unmatched. The Western movie star won three Academy Awards for Best Supporting Actor in just five years – an achievement that led the Oscars to change their voting rules.
Before Hollywood, Brennan served in World War I, where mustard gas exposure gave him his signature high-pitched voice. He dabbled in real estate, lost his fortune, and then started working as a film extra. By the 1930s, he had appeared in over 100 films before landing his breakthrough role in The Wedding Night (1935). That opened the door to bigger parts, leading to Oscar wins for Come and Get It (1936), Kentucky (1938), and The Westerner (1940).
Brennan’s popularity with the extras’ union, which had voting power at the time, was a big pull. His fellow background actors adored him, and their support helped him dominate the Oscars. But after his third win, the Academy changed the rules, barring extras from voting. The very next year, Brennan lost for the first time, despite a nomination for Sergeant York (1941). With over 230 screen credits, he remains one of Hollywood’s most prolific character actors.
6. Frances McDormand
Frances McDormand has spent nearly 40 years doing things her way, earning three Oscars and seven nominations along the way. She’s one of Hollywood’s most talented and respected. Her big break came with Blood Simple, the Coen Brothers’ first film, where she met her future husband, Joel Coen.
They’ve worked together on several classics, including Fargo, which won her her first Academy Award for Best Actress. She later won again for Three Billboards Outside Ebbing, Missouri, playing a fierce mother demanding justice.
Her third Oscar came with Nomadland, a film about life on the road. Beyond her wins, McDormand has also been nominated for Mississippi Burning, Almost Famous, North Country, and Nomadland (as a producer).
5. Daniel Day-Lewis
Daniel Day-Lewis stunned Hollywood in 2017 when he announced his retirement. Over his career, he became the only man to win Best Actor three times – first for My Left Foot (1989), then There Will Be Blood (2007), and finally Lincoln (2012).
He earned six Oscar nominations in total, with nods for In the Name of the Father (1993), Gangs of New York (2002), and Phantom Thread (2017). Day-Lewis took on an astonishing range of roles, from the ruthless Bill the Butcher in Gangs of New York to the tortured fashion designer in Phantom Thread.
If his retirement holds, he would not be worried, for someone who has already left an unmatched body of work. Few have ever done it better.
4. Ingrid Bergman
Hollywood has a long tradition of rewarding actors for the wrong roles, and Ingrid Bergman might be a good prime example. She wasn’t even nominated for Casablanca or Notorious, yet won three Oscars for performances that don’t hold nearly the same cultural weight.
Gaslight, for which she won her first, gave her a solid playing field – she runs the gamut from mild anxiety to full-blown hysteria – but everything’s on the surface. Compare that to her frustration in Stromboli, and it’s clear she was capable of much more.
Her second win, for Anastasia, is similarly baffling – it’s a fine performance in a film few revisit. Then there’s her Supporting Actress win for Murder on the Orient Express, where she’s barely in the movie. Bergman was undeniably great, but her Oscars tell the wrong story.
3. Jack Nicholson
Few actors have had careers this stacked. With a whopping 12 Oscar nominations, one of the highest ever, Jack Nicholson has won three times, putting him in a small, elite club of actors with only six members.
His first Oscar nod came from Easy Rider (1969), and he followed it up with Five Easy Pieces (1970), The Last Detail (1973), and Chinatown (1974) – a rather insane run of nominations. But it was One Flew Over the Cuckoo’s Nest (1975) that finally won him his first Oscar.
The ’80s brought another win with Terms of Endearment (1983), followed by nominations for Prizzi’s Honor (1985) and the now-forgotten Ironweed (1987). In the ‘90s, he stole scenes in A Few Good Men (1992) and grabbed his third win with As Good as It Gets (1997). His final nod came from About Schmidt (2002).
2. Meryl Streep
The most-nominated actor in history, if nominations counted as wins, she’d be #1, Meryl Streep is in a league of her own. With 21 nominations, she holds the record for the most nods in acting categories – far ahead of legends like Jack Nicholson and Katharine Hepburn, who each have 12.
Since her first nomination in 1978 for The Deer Hunter, she’s been a constant at the Academy Awards, earning recognition for roles across every genre imaginable.
While these nominations showcase her incredible versatility and longevity, she’s also taken home three Oscars. Best Supporting Actress for Kramer vs. Kramer and Best Actress for Sophie’s Choice and The Iron Lady. With her career still going strong, it wouldn’t be surprising if she added another golden statue to her collection. That’s what we have come to expect out of Streep, anyway.
1. Katharine Hepburn
Katharine Hepburn remains the most decorated performer in Academy Awards history, holding an unbeaten record of four Best Actress wins. She won her first Oscar in 1934 for Morning Glory, just three films into her career, but her unconventional choices soon led to a decline in popularity. Labeled “box office poison” by 1938, she staged one of Hollywood’s greatest comebacks with The Philadelphia Story (1940), earning another Oscar nomination.
Despite six more nods, she wouldn’t win again until 1968 for Guess Who’s Coming to Dinner, quickly followed by The Lion in Winter in 1969 – making her only the third performer to win back-to-back Oscars. Her final win came in 1982 for On Golden Pond, setting records for the longest span between first and last wins, and for being the oldest winner at the time.
Hepburn’s 12 acting nominations stood as the record until Meryl Streep surpassed her in 2003. Yet, unlike many of her peers, she famously skipped nearly every ceremony, only appearing once in 1974 to present an honorary award.
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