10 Celebrities Who’ve Won an “Oscar” for Best Actor but Who’ve Also Failed in the Simplest of Roles

10 months ago

An actors’ life is not easy — today you are applauded by viewers and critics who say you deserve the best awards in cinematography, but tomorrow you might be given an award for the worst actor or actress. Not all of them manage to keep the bar high, even famous and experienced actors don’t always manage to do it. Who could have ever imagined that the 3 main characters of The Irishman by Martin Scorsese would turn out to be experienced nominees for the “Golden Raspberry” (an award that honor the worst achievements in cinematography)?

Bright Side went through the filmographies of actors who were awarded an “Oscar” and an “anti-Oscar” and outlined their best and worst roles.

Natalie Portman

The best role: Ballerina Nina Sayers in Black Swan. Natalie went all in for this role. She started her ballet lessons one year prior to shooting. At first, she trained for 2 hours every day, then she increased the duration of her classes to 5 hours a day.

On set, she got a concussion and damaged ribs. It took 6 weeks for her to recover. In addition, the mental state of the actress was said to be unstable. As a result, Portman was nominated for various awards for her efforts, having won almost all of them, including an “Oscar” and a “Golden Globe.”

The worst role: Queen Padmé Amidala, Star Wars: Episode II — Attack of the Clones. 2 parts of Star Wars brought her nominations for “Golden Raspberry Awards.” In 2003, Natalie and Jake Lloyd were called the worst on screen couple and in 2003, Portman almost became the worst supporting actress. Later in her interview, Portman said, " Everyone thought I was a horrible actress. I was in the biggest-grossing movie of the decade, and no director wanted to work with me."

Al Pacino

The best role: Frank Slade, Scent of a Woman. Al Pacino has been nominated for an “Oscar” 9 times, but he won it only once. The role of a blind, retired Army officer became a real test for him and demanded his maximum-level acting skills. Critic Marjorie Baumgarten outlined Al Pacino’s perfect acting, saying that it made you forget about everything happening outside the screen.

The worst role: Cameo, Jack and Jill. It’s ok to stumble with such a long cinema career and that’s what Al Pacino did... 4 times. At the same time, he became a laureate of the “Golden Raspberry” only once. But it’s worth noting that the film Jack and Jill received a lot of negative feedback in general and was named the worst film of the year. 3 other projects where the actor showed his worst side were Revolution, Gigli, and 88 Minutes.

Charlize Theron

The best role: Aileen “Lee” Wuornos, Monster. In 2004, the actress won a lot of awards for working on this picture. The fact that she transformed herself drastically and left her comfort zone as a sweet girl, helped her achieve success.

The worst role: Sara Deever, Sweet November. This is a favorite film for anyone who loves to cry over a melodrama. But it’s this movie that got Charlize her first nomination for the “Golden Raspberry Award.” Critics blitzed the movie to smithereens. The screen couple played by Charlize Theron and Keanu Reeves also got a tongue lashing from the critics because of the absence of any chemistry between them.

Robert De Niro

The best role: boxer Jake LaMotta, Raging Bull. One of the first nominations for Robert De Niro for an “Oscar,” was in 1975 when he won the award for Best Supporting Actor in The Godfather: Part II. In 1981, he won it for Best Actor in Raging Bull. Moreover, he has been nominated for an “Oscar” 6 more times during his acting career.

The worst role: Dick Kelly, Dirty Grandpa. It is impossible to assert with complete certainty that the longer a career is, the worse the movies become. De Niro’s last movie called The Irishman had high chances to become the best movie of 2020. However, failures happen too. In 2017, the actor played in the movie Dirty Grandpa that was so unsuccessful, it eventually got the “Golden Raspberry Award.”

Nicole Kidman

The best role: Writer Virginia Woolf, The Hours. Kidman read all the letters that were published by Woolf. As the actress later admitted, it really helped her to get used to the role and understand her character. Also, Nicole had to learn to write with her right hand because she is left-handed.

The worst role: Devlin Adams, Just Go with It. The main stars in this comedy were, of course, Jennifer Aniston and Adam Sandler, but people still managed to notice the bad acting of Nicole Kidman. Critic Wesley Morris from The Boston Globe said, “Seeing her in junk like this is a bit like watching the Queen of England eat a Taco Bell chalupa.”

Joe Pesci

The best role: Tommy DeVito, Goodfellas. All 3 movies where Joe Pesci was nominated for an Academy Award have co-starred Robert De Niro. In Goodfellas, they played 2 gangsters who can’t imagine any other kind of life, apart from being criminals. The movie even included scenes taken from Pesci’s past.

The worst role: Leo Getz, Lethal Weapon 4. The film as a whole turned out to be worse than the prequels that came before it. Joe Pesci’s acting was not as skillful as in Scorsese’s movies. That’s why, in 1999, he was nominated for the “Golden Raspberry Award” for the Worst Supporting Actor.

Julianne Moore

The best role: Linguistics professor Alice Howland, Still Alice. In 2015, Julianne Moore got the “Oscar” for her work in this movie. When preparing for it, the actress consulted The Alzheimer’s Association employees to be able to better show the changes that were taking place in her character’s life. David Hughes from Empire called Julianne Moore’s acting perfect.

The worst role: Mother Malkin, Seventh Son. The next year after getting the “Oscar” award, the actress was nominated for “The Golden Raspberry Award” for the Worst Supporting Actress in Sergei Bodrov’s movie. The project, as a whole, was perceived very negatively and received a low rating from both critics and viewers.

Jesse Eisenberg

The best role: Mark Zuckerberg, The Social Network. The role of Facebook founder got Eisenberg a nomination for the “Oscar” and other prestigious awards in 2011. And though the actor’s portrayal impressed even the most skeptical viewers, Jesse hasn’t been noticed in other significant drama roles since then.

The worst role: Lex Luthor, Batman v Superman: Dawn of Justice. DC Entertainment company expected a huge breakthrough from this movie, but they ended up creating something slurred. Critic Tasha Robinson describes Eisenberg’s acting as “a manic, lighter version of Heath Ledger’s Joker from The Dark Knight, all nervy babble, alarming tittering, and nihilistic challenges to the world.” In her review, Tasha outlines, “This Lex lacks the Joker’s sense of menace, or even focus; his sneakers, shaggy hair, and squeaky voice are overtly non-threatening, even when he’s in the middle of a threat.”

Rooney Mara

The best role: Therese Belivet, Carol. That year the actress didn’t get the “Oscar,” she was outpaced by Alicia Vikander. Nevertheless, the role was noted by many and people started to talk about Rooney Mara as a talented actress. Earlier, she also managed to reveal her creative potential in the movie The Girl with the Dragon Tattoo for which she was nominated for an “Oscar” too.

The worst role: Tiger Lily, Pan. The movie had every chance to be successful. The script it was based on was on “The Black List” of the “most liked” and not yet produces projects. The cast was full of world-famous celebrities: Hugh Jackman, Garrett Hedlund, Amanda Seyfried.

But it seems that Rooney Mara was defeated before she even had a chance to begin, during casting. The filmmakers were accused of racism and inconsistency with the canon since the character of Tiger Lily was supposed to be an Indian princess. Many critics agree that the actress should not have taken on this role at all.

Leonardo DiCaprio

The best role: Frontiersman Hugh Glass, The Revenant. The entire world had been waiting for this event and, finally, in 2016, Leonardo DiCaprio did it — he got his long-awaited Oscar. The actor had been preparing for this role for a long time, he discussed all the important moments and tiniest nuances with director Alejandro G. Iñárritu.

Leonardo got into this role so much that he was eating raw meat on set, while being a vegetarian in real life. After the release of the movie, almost all of the critics agreed that DiCaprio was the main nominee for the Academy Award in 2016.

The worst role: Young American guy Richard, The Beach. In 2001, the actor was nominated for the Golden Raspberry Award for the worst acting. Stephen Hunter, from the Washington Post, outlined that the main character was “embodied by the banal beauty of DiCaprio, that big-headed, gangly boy with an adult’s voice, a child’s body, and Huck Finn’s tousle of hair.”

Why do you think even experienced actors have failures?

From being labeled “too disruptive” early in his career to becoming a sought-after Hollywood actor, Leonardo DiCaprio’s journey has been marked by resilience and determination. Despite facing numerous rejections, he remained undeterred, showcasing a mindset that prioritizes success and humility. His care for the environment and those around him further underscores his commendable character.

Please note: This article was updated in May 2022 to correct source material and factual inaccuracies.


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I love Portman in Black Swan. It was a great movie and her performance was stunning, but I believe her role in V for Vendetta was even more amazing :)


Leo wasn't that bad at The Beach actually in my opinion. Romeo and Juliet wasn't that good I believe. Plus, he was really young back then :)


Halle Berry won an Oscar for 'Monster's Ball' and a Razzie for 'Catwoman' in the same year. How this missed the list is beyond me.


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