Even Academy Award-Winning Actors Couldn’t Save These Films From Failing

Winning an Academy Award is an achievement many actors strive to accomplish. Sadly, once some hit that milestone, their careers take a major turn, and they star in projects that wind up being awful.

From Judi Dench in the atrocious film adaptation of Cats to Jack Nicholson and Morgan Freeman in The Bucket List, there's more than one Oscar-winner that's appeared in a lousy movie.

Robert De Niro In Dirty Grandpa

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Lionsgate via MovieStillsDb

The film Dirty Grandpa is definitely a stain in Robert De Niro's otherwise stellar resume. A two-time Academy Award-winning actor, De Niro took up the role of Zac Efron's grandpa in the 2016 movie; a mistake.

The film wound up earning a 10% on Rotten Tomatoes, and De Niro was even nominated for a Golden Raspberry Award for Worst Actor.

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Halle Berry In Catwoman

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Taking on one of the most beloved anti-heroes in the DC universe should have been a sure thing for an Academy Award-winning actress like Halle Berry. Alas, even the Best Actress award for her performance in Monster's Ball couldn't save Catwoman.

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In three years, Berry went from an Oscar winner to a Razzie winner, both for Best Actress.

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Renée Zellweger In Case 39

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Renée Zellweger's future in the entertainment industry looked bright after winning an Academy Award for Best Supporting Actress for Cold Mountain. Then, Case 39 happened.

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The film was beaten down by critics, with some saying the film could have easily cost Zellweger her career. Thankfully, the awful movie didn't stop the actress, and she wound up winning an Oscar for Best Actress for the biopic Judy in 2020.

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Jon Voight In Superbabies: Baby Geniuses 2

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Since his Academy Award-winning performance in Coming Home, Jon Voight's career has been unpredictable at best. He's been in some more great motion pictures and then goes and stars as a villain in films like Superbabies: Baby Geniuses 2.

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The box office flop is widely considered one of the worst films ever made and earned a Razzie nomination for Worst Picture.

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Viola Davis And Jared Leto In Suicide Squad

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Viola Davis is one of the few who has won the iconic "Triple Crown," including an Academy Award. In 2016, she starred alongside fellow Oscar-winner Jared Leto in Suicide Squad, which did little to move either actor's career along.

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The highly-anticipated film was a major bust. Critic Richard Lawson even went as far as saying, "Suicide Squad is just bad. It's ugly and boring, a toxic combination..."

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Nicolas Cage In Season Of The Witch

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It is no secret that Nicolas Cage has been his fair share of horrible movies. But Season of the Witch might just top his resume as the absolute worst. The Academy Award-winner played the role of Behmen von Bleibruck, a knight charged with bringing a supposed witch in and destroying her powers.

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It didn't work out as planned. One critic didn't hold back, saying, "Cage was the primary reason that this swords-and-sorcery romp is a colossal [sic] waste of time." Cage was nominated for a Worst Actor Razzie Award.

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Jack Nicholson And Morgan Freeman In The Bucket List

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When a three-time Academy Award-winning actor, Jack Nicholson, gets together with another Oscar winner, Morgan Freeman, one would think the result would be unimaginable. Well, it was, but not for the right reasons.

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Many critics, especially Roger Ebert, did not appreciate how The Bucket List illustrated cancer survivors, giving the film a one-star rating to go along with its 41% on Rotten Tomatoes.

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Matthew McConaughey In The Dark Tower

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Actor Matthew McConaughey made it a point to get out of his rom-com persona and be taken seriously as an actor. It worked, earning him an Academy Award for Best Actor for The Dallas Buyers Club.

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Sadly, it only took four years for fans to forget that little award since The Dark Tower was miserable and his performance as the villain was viewed as "terrible."

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Forest Whitaker In Battlefield Earth

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In 2007, actor Forest Whitaker won an Academy Award for Best Actor for his performance in The Last King of Scotland. That excellent display of his acting ability was then overshadowed by the horrible performance but on in Battlefield Earth.

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He might be an Oscar winner, but Whitaker will forever be connected with what is often considered one of the worst films ever made.

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Sandra Bullock In All About Steve

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Sandra Bullock is one of those rare actors who picked up her Razzie one night only to win an Academy Award for Best Actress for The Blind Side the following evening. The former award was for her performance in the film All About Steve.

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With a solid 6% on Rotten Tomatoes, the film is one of the worst on the fan-favorite actress's resume.

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Julia Roberts In Mother's Day

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Julia Roberts has a long list of projects and accolades to her name, including an Academy Award for Best Actress for her performance in Erin Brockovich. Sadly, she also has the film Mother's Day on her resume, a film that wound up earning her a Golden Raspberry nomination for Worsts Actress.

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The film has a solid 8% on Rotten Tomatoes and was called "the cinematic equivalent of a last-minute gift that only underscores its embarrassing lack of effort."

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Roberto Benigni In Pinocchio

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While the original Italian version of the 2002 film Pinocchio received mixed reviews, the English-language dubbed version was dragged through the mud. While Roberto Benigni was coming off his 1999 Academy Award win for Life is Beautiful, there was nothing beautiful about the creepy film.

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One reviewer wrote, "Roberto Benigni misfires wildly with this adaptation of Pinocchio, and the result is an unfunny, poorly-made, creepy vanity project." The film holds a 0% on Rotten Tomatoes.

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Marlon Brando In The Island of Dr. Moreau

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Actor Marlon Brando is one of the lucky actors who actually has two Academy Awards to his name. Sadly, the prestigious awards didn't save him from starring as a mad scientist in The Island of Dr. Moreau.

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With that one film, Brando went from being a two-time Oscar winner to the proud owner of a Razzie for Worst Actor.

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Sir Anthony Hopkins In The Rite

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Even two-time Academy Award-winning actor Sir Anthony Hopkins couldn't keep the 2011 film The Rite from flopping. While Hopkins's performance in the film was widely praised, the movie as a whole was not.

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Sitting with a 21% on Rotten Tomatoes, one reviewer wrote, "Anthony Hopkins is as excellent as ever, but he is no match for The Rite's dawdling pace and lack of chills."

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Jennifer Hudson And Dame Judi Dench In Cats

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Actresses Jennifer Hudson and Dame Judi Dench are both Academy Award winners. But that title meant nothing when it came to the film adaptation of the Broadway play Cats. The film lost Universal an estimated $71-$114 million at the box office.

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After numerous horrible reviews from critics, namely about the horrifying CGI cats, it has been branded as one of the worst films of all time and called "one of those once-in-a-blue-moon embarrassments that mar the résumés of great actors."

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Gwyneth Paltrow In Mortdecai

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While Gwyneth Paltrow's Academy Award win for Best Actress was in 1998, fans had high hopes for her career. Then, she starred as the wife of a shady art dealing aristocrat in Mortdecai.

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The film is definitely a rough spot on Paltrow's resume, earning her a Golden Raspberry Award for Worst Actress as well as the film garnering a 12% on Rotten Tomatoes.

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Al Pacino In Jack And Jill

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Adam Sandler did Al Pacino wrong when he wrapped Pacino into appearing as himself in Jack and Jill. The Academy Award-winning actor wound up winning a Razzie Award for his performance in what is considered one of the worst films of all time.

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It's a far cry from his outstanding resume filled with top-notch mob films.

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Whoopi Goldberg In Theodore Rex

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New Line Cinema via MovieStillsDb
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Six years after winning the Academy Award for Best Supporting Actress in Ghost, Whoopi Goldberg makes a questionable career choice. In 1996, she starred as police detective Katie Coltrane in Theodore Rex, a film exploring a futuristic world where humans and dinosaurs coexist and communicate.

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During an interview with Brazilian newspaper Folha de S.Paulo, Goldberg spoke of the movie, saying, "Don't ask me why I did it; I didn't want to." The film has a solid 0% on Rotten Tomatoes and went straight to video.

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Hilary Swank In The Reaping

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Hilary Swank starred as Katherine Winter in the 2007 supernatural horror film The Reaping. A very accomplished actress who has won two Academy Awards for Best Actress, Swank made a bit of a miscalculation when she signed on for the horror film.

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The film just broke even at the box office and earned a solid 8% on Rotten Tomatoes for being "schlocky, spiritually shallow, and scare-free."

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Emma Stone In Aloha

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The 2015 rom-com Aloha was surrounded by a lot of controversies upon its release, namely about Captain Allison Ng, played by Emma Stone. The actress actually publicly apologized for her character, someone who is supposed to be of Hawaiian and Asian ancestry (Stone is not).

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Stone made it up to her fans by taking on La La Land, a musical romance film that earned the actress an Academy Award for Best Actress.

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Cuba Gooding Jr. In Boat Trip

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Although Cuba Gooding Jr. earned quite a feather in his cap with his Oscar-winning performance in Jerry Maguire, it only took five years before his career was in trouble. Indeed, 2002 seemed to be a particularly rough year for him, as both Snow Dogs and Boat Trip were considered embarrassing career moves.

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However, Boat Trip has since grown into the worst of the two, as Snow Dogs at least has some cute dogs in its favor. Whereas Boat Trip is not only working with the distasteful premise of a straight man on a gay cruise luring a woman into intimate situations by tricking her into thinking he's gay, but was also consistently unfunny both at the time and since.

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Mel Gibson in The Singing Detective

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Although a roadside rant during a DUI arrest in 2006 would do far more damage to Mel Gibson's career than any movie, it still likely wasn't a point of pride that one of the last movies he starred in before this incident was The Singing Detective.

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The premise is interesting, as the extreme psoriasis patient under his care (played by Robert Downey Jr.) hallucinates entire plots and musical numbers from his hospital bed, but the movie drags significantly in trying to explore this premise. An interesting idea can wear out its welcome quicker than it may seem if the execution is plodding.

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Eddie Redmayne in Jupiter Ascending

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It's no secret that Jupiter Ascending was a confusing and oddly boring mess for how insane it is on paper, but it's a matter of perspective as to whether Eddie Redmayne's performance as Balem Abrasax is the best or worst part of it.

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Considering how little there is for audiences to grab onto in many scenes, his bizarre performance that sees him abruptly shift from whispering to yelling (seemingly at random) at least provides some bewildering amusement. In fairness, Redmayne was almost certainly directed to do that.

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Emil Jannings in Ohm Krüger

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Sometimes, the issue with an Oscar winner's post-award work doesn't have anything to do with the technical aspects of a film, its narrative finesse, or even the actor's performance. Sometimes, the issue is with the purpose the actor's performance is serving.

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For Emil Jannings, the first Oscar winner for Best Actor, the purpose of every film he made after 1933 was to glorify and propagandize for the German government, both before and during its aggression that led to the outbreak of World War II. Ohm Krüger was considered one of the most successful of these "state films," which also made it one of the reasons he would never find work as an actor again after the war.

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Will Smith in After Earth

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Although After Earth came before Will Smith's Pyrrhic Academy Award win in 2022, it nonetheless stands out as one of the most embarrassing entries in his filmography. With a story developed by him as a co-starring vehicle for him and his son Jaden, the film's muddled, confused narrative rests largely at his feet.

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In addition to the film's logical inconsistencies, it was criticized for both Smiths' bizarre performances and even their distracting futuristic accent choices. Although the premise may have been interesting in the right hands, it seemed that neither Smith nor director M. Night Shyamalan had the right hands.

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Adrien Brody in Blonde

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Adrien Brody's presence in the controversial 2022 Marilyn Monroe biopic Blonde is fitting, as it's widely regarded as a lurid, distasteful film that attempts to buoy itself with stellar performances. While Ana De Armas earned an Oscar nomination for her portrayal of Monroe, the movie "won" a Golden Raspberry Award overall.

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In addition to its filmmaking sins, the film was criticized for bastardizing the actual struggles Monroe went through and inventing further cases of abuse for exploitative purposes. Those who lamented that the maligned 1989 John Belushi biopic Wired reduced Belushi to his addictions will likely take a similar issue with Blonde.

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Anne Hathaway in The Witches

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Although Anne Hathaway's post-Oscar career challenges largely aren't her fault, it's still true that her performance as the Grand High Witch in the 2020 remake of The Witches is likely among her weakest. However, there's also plenty of failure to go around behind this movie's release.

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In addition to the wide perception of this film as an unnecessary remake of the imaginative and intriguing 1990 adaptation of Roald Dahl's novel, The Witches was also criticized for being overall stiffly acted and uninspired in its storytelling.

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Natalie Portman in Star Wars Episode II: Attack Of The Clones

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While it's true that some Star Wars fans like to lay the serious deficiencies of Attack Of The Clones at Hayden Christiansen's feet, the fact that future Oscar winner Natalie Portman seemed just as unconvincing in the film's key romantic plot as he did indicates the film's flaws go deeper than anyone's performance.

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Whether fans want to admit it or not, George Lucas's embarrassing script and the sterile direction of his actors are the most significant factors for why the movie's romantic scenes are so painful to sit through. There's also nobody else to blame for why there are so many of them.

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Gary Oldman in Tiptoes

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Due to his uncanny propensity to disappear into any role he plays, Gary Oldman could make a legitimate case for himself as one of the best actors in movie history. However, even the very best can end up taking regrettable roles, and it's fair to call his starring turn as a little person in the 2002 film Tiptoes the perfect example.

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Interestingly, co-star Peter Dinklage insisted that the film's director's cut was legitimately moving, but that Tiptoes was massacred by the studio before its release. However, since most others involved would prefer to pretend the movie never existed, this cut isn't likely to be seen by the public.

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John Wayne in The Conqueror

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It's hard to think of a more embarrassing example of miscasting than John Wayne's infamous starring role in the Genghis Khan biopic The Conqueror. Indeed, Wayne himself appeared to agree, readily admitting after the fact that it was a role he wasn't suited for.

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Worse yet, there's a strong possibility that this movie contributed to his death. Although it's true that there were other possible lifestyle factors behind his eventual cancer diagnosis, filming in a desert that had been subject to atomic testing is still a plausible candidate for the culprit behind his terminal illness.