Winning an Academy Award is probably the most coveted honor in the film industry. For actors in particular, winning an Oscar can be a terrific boost to their career in every sense, from the quality and quantity of roles they get to an increase in pay to just general prestige in the eyes of the public and the industry. However, this achievement has sometimes proved to be less of a blessing and more of a curse.
Throughout the years, there have been plenty of actors and actresses who peaked with their Oscars. Whether that means that they never delivered a performance quite as good as their Oscar-winning one again, they shifted away from mainstream Hollywood, or they pretty much vanished altogether,these thespians prove that becoming an Oscar-winning actor doesn’t actually push your career forward. These actors are listed in chronological order of the Oscar wins that they peaked with.
1Elizabeth Taylor
Won: Best Actress for ‘Who’s Afraid of Virginia Woolf?’ (1966)
The legendaryElizabeth Taylorwas one of the biggest icons of Hollywood’s Golden Age, but she delivered her greatest performanceafterthe end of American cinema’s Classical period: as Martha in the masterful psychological dramaWho’s Afraid of Virginia Woolf?Her performance here is typically praised as one of the greatest in the history of American cinema, and rightfully so.
Who’s Afraid of Virginia Woolf?in general is one ofthe best movies of the 1960s, and back when it came out, Taylor’s performance was lauded by critics with words like sensual, tender, and pitiable. As such, it was hardly a big surprise when the actress won her second Oscar for this film, just six years after she won her first forBUtterfield 8. But where does an actor go after summiting the proverbial Everest in this way? Indeed, having proven everything she had to prove,Taylor never delivered a performance nearly as titanic again. She definitely didn’t vanish from the spotlight, as she kept working in movies all the way into the ’90s (and tabloid journalists certainly kept loving digging into her privacy post-Oscar just as much as before), but this was undoubtedly the peak of her career.
Who’s Afraid of Virginia Woolf?
2Tatum O’Neal
Won: Best Supporting Actress for ‘Paper Moon’ (1973)
Paper Moonis a great comedy caper and one of themost touching films about father-daughter relationships, but it’s perhaps best known for the putting-together of its two stars: real-world father and daughterRyanandTatum O’Neal. While Ryan wasn’t even nominated for an Oscar for his work inPaper Moon, Tatum wasn’t just nominated—she won, and to this day, she’s stillthe youngest Oscar winner in history.
It’s notorious that Ryan was allegedlyquite jealous of her daughter’s victory, and what followedPaper Moonfor Tatum wasa pretty uneven careermarked by addiction and difficulty finding a role as perfect as the one that earned her an Academy Award. The actress certainly displayed talent on repeated occasions many times throughout the years, but she never rocked audiences' world like she did in the movie that made her a star.
Paper Moon
3Roberto Benigni
Won: Best Actor for ‘Life is Beautiful’ (1997)
It’s not often (and it was particularly uncommon back in the 20th century) that a foreign film gains as much traction in the Academy Awards asLife is Beautifuldid at the 1998 Oscars. Distributed by convicted sex offenderHarvey Weinstein(which makes its awards success less of a mystery), the movie was directed and cowritten by its star,Roberto Benigni.
Many would call Benigni’s humorous performance in this offbeat Holocaust film theweakest Best Leading Actor winner of the ’90s, but it’s nevertheless a pretty solid performance in an often misunderstood film. Whatever the case, Benigni captured lightning in a bottle with this endearing slapstick performance becausehe would never find the same kind of critical or audience lovethat he did withLife is Beautifulagain. He mostly kept working in Italy, making the infamous flopPinocchioin 2002, but even in his native country, his style of comedy seemed to have fallen out of style.
Life Is Beautiful
4Kim Basinger
Won: Best Supporting Actress for ‘L.A. Confidential’ (1997)
The iconicL.A. Confidentialis a paragon of the neo-noir genre, particularly as far as its representation in the 1990s is concerned. And, like any great neo-noir, it has a phenomenal femme fatale inKim Basinger’s Lynn Bracken. While some might agree that Basinger is perhaps theweakest Supporting Actress Oscar winner of the ’90s, she’s definitely not without her fans, and her performance is nevertheless exceptional.
Basinger pretty much swept all awards that season, proving that her performance inL.A. Confidentialwas very much considered the best of her career at the time. Sadly, it would prove toforeverremain the best of her career.She didn’t seem to know how to pick good, prestige roles after her Oscar win, working on things like the failed Oscar baitI Dreamed of Africa. There’s also the undeniable truth that women in Hollywood are held to much different standards than men after a certain age, even if (or, sometimes, particularly after) they win an Academy Award. Basinger was 44 when she won her Oscar, meaning that that probably also contributed to her pretty much slipping under the radar at some point during the 21st century.
L.A. Confidential
5Hilary Swank
Won: Best Actress for ‘Million Dollar Baby’ (2004)
Hilary Swankgot her first Oscar nomination and win in 2000 forBoys Don’t Cry. Five years later, she received her second nomination, forClint Eastwood’sMillion Dollar Baby—and she won that one, too. Following that second win, she did try to get a third, including the blatantly obvious (and thoroughly terrible) Oscar bait biopicAmeliafrom 2009, but she hasn’t tasted Oscar gold (or even come particularly close, quite frankly) since.
Swank tried other kinds of roles and genres following her Oscar win, butshe didn’t really find roles that brought her the same kind of recognitionthat her second Oscar-winning one did. True industry prestige would only come back to greet her when she was nominated for a Golden Globe in 2023 for her performance in the crime drama showAlaska Daily, but it was canceled after just one season, contributing to the truthfulness of saying that Hilary Swank peaked back in 2004.
Million Dollar Baby
6Sean Penn
Won: Best Actor for ‘Milk’ (2008)
2008 was a hell of a year for movies, and one of the year’s best isMilk, a biopic about the American gay activistHarvey Milk, who was elected as California’s first openly gay official in 1977. The movie itself is great, but it’s pretty much universally agreed (and the Academy clearly thought so, too) that the main reason to watch it isSean Penn’s terrific performance as Milk.
Penn’s courageous performance hereconstitutes one of the best Leading Actor wins of the 21st century, but after 2009, his career started dwindling.
The actor had already won his first Oscar back in 2004 for Clint Eastwood’sMystic River—much flashier actorial work but narratively inferior toMilk. Penn’s courageous performance hereconstitutes one of thebest Leading Actor wins of the 21st century, but after 2009,his career started dwindling. He started being the center of all sorts of controversies (though he was alreadya controversial figure before 2009), and he seemed to stop knowing how to pick roles that would find him the same kind of recognition he got forMilk. Or perhaps people just stopped hiring him because of his notoriously difficult behavior. Maybe both.
Won: Best Supporting Actress for ‘Precious’ (2009)
It’s usually fascinating when a comedian breaks type and gets cast in a dramatic role, something that actors likeJim CarreyandRobin Williamsare famous for. But never had an against-type dramatic performance by a comedian beenas gut-wrenchingly devastatingasMo’Nique’s work inPrecious, far and away one of the saddest movies of the 2000s.
According to Mo’Nique, she accepted relatively low compensation forPreciousbecause she was friends with directorLee Daniels. But when the film became a surprise hit at the box office, Daniels and producersTyler PerryandOprah Winfreywanted her to do more promotion than she was contractually obligated to do for essentially no extra pay, to which she said no. After that, Mo’Nique was allegedly labeled “difficult to work with” by the trio. In other words,she was blacklisted, and her career in Hollywood was virtually overright then and there. It’s a shame that she never got another chance to prove her acting chops because her work inPreciousis one of the greatest performances of the 21st century thus far.
8Melissa Leo
Won: Best Supporting Actress for ‘The Fighter’ (2010)
Melissa Leo’s performance inThe Fighteris definitely not the best of the film (it might not even be the best female supporting performance in the movie, withAmy Adamsright there), but it was great enough that she swept the entire 2011 awards season, and the Academy unsurprisingly gave her the Supporting Actress award.
Though this victory gave the world one ofthe worst Oscar acceptance speeches of all time, Leo still does some pretty exceptional work inThe Fighter, which makes things slightly less upsetting. She also had a great narrative, as a veteran actress who had been grinding for an Oscar for a long time, which the Academy loves. But after her win, this character actress began starring inall kinds of projects that simply didn’t live up to the standardshe had set withThe Fighter.The market got a little oversaturated with Melissa Leo, but since none of those performances were nearly as extraordinary as the one that earned her an Oscar, audiences got a bit tired.
The Fighter
9Brie Larson
Won: Best Actress for ‘Room’ (2015)
A24’sRoomis a volcanic drama brimming with emotions often hard to stomach but always memorable and profoundly moving. It’s all anchored by a pair of unbelievably great performances byJacob TremblayandBrie Larson, the latter of whom dominated the 2016 awards season and thus ended up taking the Best Leading Actress trophy home.
The thing about actors gaining prestige in modern Hollywood is that now, the ultimate target seems to be to become a franchise star. That’s precisely the direction that Larson’s career took, putting her in projects likeKong: Skull Islandand, most notoriously, the Marvel Cinematic Universe, starting withCaptain Marvel. Larson remains well-regarded in the industry, butshe spent most of her Oscar capital in Marvel, and it didn’t turn out the way we hoped it would. Larson has definitely offered great performances sinceRoom, even receiving an Emmy nod forApple’sLessons in Chemistry, butnone nearly as exceptional or prestigious.
10Ariana DeBose
Won: Best Supporting Actress for ‘West Side Story’ (2021)
Since he had never directed a musical before, no one expectedSteven Spielberg, of all people, to be the one to remake the iconicWest Side Story.Much less did they expect the movie to be so remarkably good, even if it underperformed at the box office. But despite its financial problems, the film was an Oscar darling and earnedAriana DeBoseaverywell-earned Supporting Actress Oscar for her portrayal of Anita, a role for whichRita Morenoalso won an Oscar back in 1962 for the original movie adaptation of the Broadway musical.
But whileWest Side Storyis one ofthe best musicals of the 2020sand DeBose was stellar in it, the projects that she has taken on since then have been less than remarkable.Wish(an animated Disney movie),Kraven the Hunter(a big franchise film), andLove Hurts(an action movie alongside another Oscar winner,Ke Huy Quan) have all looked like solid career choices on paper but have proved abysmal in practice. One can onlyhope that DeBose and her agent can get her career back on trackbecause, if her tantalizing performance inWest Side Storyis any indication,she’s an actress with an awful lot to offer.
