A lot of actors look back on their biggest roles with regret, even though everybody loved their characters.

A lot of actors look back on their biggest roles with regret, even though everybody loved their characters.


December 18, 2025 | Peter Kinney

A lot of actors look back on their biggest roles with regret, even though everybody loved their characters.


After The Spotlight Fades

Many actors take on roles that later come back to haunt them. For some stars, even parts that made them rich and famous also left them with regret, discomfort, or awkward memories in the light of years of hindsight. In this list, we explore notable stars whose most iconic roles didn't age how they hoped.

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Timothée Chalamet As Gatsby Welles

In A Rainy Day In New York (2019), Timothée Chalamet plays privileged student Gatsby Welles. But after renewed scrutiny of director Woody Allen, Chalamet announced his regrets for taking on the role. He even donated his salary to charities supporting abuse survivors, in an attempt to show his decision no longer aligned with his values.

A Rainy Day in New York TrailerScreenshot from A Rainy Day in New York, MPI Media Group (2019)

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Matt Damon As Jason Bourne

Matt Damon doesn’t regret being Jason Bourne overall, but he did have some harsh words to say about The Bourne Ultimatum (2007). He called an early script draft “unreadable,” saying the film almost drove a stake through the heart of the franchise. The career misstep still rankles him when he contemplates the series’ impact.

Matt Damon in The Bourne Ultimatum (2007)Screenshot from The Bourne Ultimatum, Universal Pictures (2007)

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Zac Efron As Troy Bolton

Zac Efron became a global teen idol as Troy Bolton in Disney’s High School Musical (2006–2008) trilogy. He has stated in interviews that he gets frustrated when audiences pigeonhole him into the squeaky-clean Disney persona rather than acknowledging the more mature work he’s done in the years since then.

Screenshot from American musical television film High School Musical (2006)Screenshot from High School Musical, Disney Channel (2006 - 2008)

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Sally Field As Aunt May

Sally Field took the role of Aunt May in The Amazing Spider-Man (2012) partially as a favor. She later noted the character’s limitations, saying there was no way to make her three-dimensional and that she felt constrained by a shallow script that allowed very little room for added complexity.

Sally Field As Aunt MayScreenshot from The Amazing Spider-Man, Columbia Pictures (2012)

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Harrison Ford As Rick Deckard

Even though Blade Runner (1982) is now considered a sci‑fi classic, Harrison Ford has also said he “didn’t like the movie one way or the other.” He always felt that his detective, Rick Deckard, lacked real agency and that he never fully connected with the ideas of the film until long after its release.

Screenshot from the movie Blade Runner (1982)Screenshot from Blade Runner, Warner Bros. (1982)

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Christopher Plummer As Captain Von Trapp

Christopher Plummer’s Captain von Trapp in The Sound Of Music (1965) is still beloved by fans, but he personally has said that he found the film “gooey” and overly sentimental. He admitted that he struggled to bring dimension to a role he felt was too stiff and saccharine for his taste.

The Sound Of Music Christopher Plummer And Julie Andrews20th Century Fox, Wikimedia Commons

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Daniel Radcliffe As Harry Potter

Daniel Radcliffe is thankful for his role in the Harry Potter series, but says he dislikes his acting in The Half-Blood Prince (2009) in particular. He’s not afraid to admit that he’d become complacent by that time in the series, and feels now that his performance was limited and “one-note,” making it hard to watch today.

Screenshot from the film Harry Potter and the Half-Blood Prince (2009)Screenshot from Harry Potter and the Half-Blood Prince, Warner Bros. Pictures (2009)

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Eddie Redmayne As Lili Elbe

Eddie Redmayne earned acclaim for The Danish Girl, but he now says casting a cis actor in the role of Lili Elbe was “a mistake.” He says he feels bad about contributing to barriers that trans actors face and now thinks that it would’ve been better if the role had gone to someone from that community.

Untitled Design (14)Screenshot from The Danish Girl, Focus Features (2016)

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Kate Winslet As Rose

Kate Winslet still says she still winces at parts of her performance in Titanic (1997). She’s often cracked jokes to the effect that she’d like to “do it all over again” when watching the film. To this day she’s unhappy with choices she made like her accent, feeling her twenty‑two‑year‑old self didn’t quite meet her later standards.

image of Rose from TitanicScreenshot from Titanic, 20th Century Fox (1997)

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Robert Pattinson As Edward Cullen

Robert Pattinson had a major career breakthrough as Edward Cullen in Twilight (), but he has often tried to distance himself from the movies by mocking the character and the films. He’s on record as struggling with the franchise’s melodramatic tone. He says the role typecast him in ways he had to work extra hard to overcome.

Screenshot from Twilight (2008)Screenshot from Twilight, Summit Entertainment (2008)

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Kristen Stewart As Bella Swan

Pattinson’s Twilight costar Kristen Stewart also had mixed feelings about Bella Swan. Despite Twilight’s success, she quickly grew tired of the obsessive scrutiny that came with the role. As a result, she has deliberately searched for roles in more unconventional films to redefine her image passed the star-crossed teen serial heroine.

Screenshot from Twilight ( 2008)Screenshot from Twilight, Summit Entertainment (2008)

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Carrie Fisher As Princess Leia

Carrie Fisher appreciated Leia’s strength in the original Star Wars trilogy but has confessed to disliking the emphasis the role put on her appearance. She especially regretted the revealing metal bikini displayed in Return of the Jedi (1983), which she felt feel objectified her and contributed to Leia overshadowing the rest of her acting career.

Screenshot of Princess Leia looking at side - from Star Wars: Episode VI - Return of the Jedi (1983)Screenshot from Star Wars: Return of the Jedi, Lucasfilm (1983)

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Alec Guinness As Obi-Wan Kenobi

Alec Guinness didn’t begrudge Star Wars’ success but also called the script “fairy-tale rubbish.” He felt the role overshadowed his long and storied dramatic career and disliked being recognized by younger people almost exclusively as the aged Jedi Master.

Obi-Wan Kenobi factsScreenshot from Star Wars: Episode IV – A New Hope, Lucasfilm (1977)

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Sean Connery As James Bond

Most Bond fans salute Sean Connery as the original and most enduring James Bond persona, but Connery has said that he eventually “hated” the character. He felt trapped by the franchise and frustrated at inability to overcome the suave spy role that overshadowed his broader range of acting abilities. Thankfully Connery enjoyed something of a renaissance in the late 80s and 90s in a variety of memorable non-Bond roles.

Sean Connery As James Bond (1971)Rob Mieremet, CC BY-SA 3.0, Wikimedia Commons

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Jennifer Lawrence As Aurora Lane

In Passengers (2016), Jennifer Lawrence plays Aurora Lane in this sci-fi romance co-starring Chris Pratt. Critics slammed the film’s ethics and story; Lawrence later conceded publicly that the film “wasn’t a good movie,” calling it one of the rare missteps in her career.

Jennifer Lawrence during Passengers Wardrobe Test - 2017Jennifer Lawrence Films, Flickr

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Ryan Reynolds As Hal Jordan

Ryan Reynolds headlined Green Lantern (2011) as Hal Jordan. The 2011 superhero epic fell right flat on its face at the box office and Reynolds has made a point of mocking the film ever since. It’s pretty clear that he saw the project was a major creative and professional miscalculation that ultimately shaped more calculated career choices later.

Screenshot from Green Lantern (2011)Screenshot from Green Lantern, Warner Bros. Pictures (2011)

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Zoe Saldaña As Nina Simone

Zoe Saldaña’s portrayal of Nina Simone in Nina drew some media backlash due to the film’s use of skin-darkening makeup and prosthetics. She later said she regretted taking on the role, believing a performer more familiar with Simone’s lived experience should have been given the chance to portray the legendary musician.

Screenshot of Zoe Saldana (Nina Simone) from - Nina (2016)Screenshot from Nina, RLJ Entertainment (2016)

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Jim Carrey As Colonel Stars And Stripes

Jim Carrey refused to promote Kick-Ass 2 (2013) after the Sandy Hook tragedy, expressing regret about endorsing extreme violence in the movies. Though he was proud of the cast and crew, he said he felt the sequel’s brutality weren’t in line with his own personal system of ethics. It created a divide he could no longer afford to ignore.

Jim CarreyJoe Seer, Shutterstock

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Molly Ringwald As Claire Standish

Molly Ringwald’s Claire Standish in The Breakfast Club (1985) became an 80s teen movie icon, but she later expressed her discomfort with the movie’s sexual politics. Rewatching the film years later as a parent, she started to question the messaging she once helped deliver, even though it was her defining role.

Screenshot from The Breakfast Club (1985)Screenshot from The Breakfast Club, Universal Pictures (1985)

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Fame Is Complicated

Iconic roles bring attention, opportunity, and long‑term recognition, but the problem is that it can come at great personal and professional cost. A wide public profile doesn’t guarantee personal and artistic satisfaction, and a single performance can shape a career in ways no one can predict until years later.

Screenshot from the movie The Twilight Saga: New Moon (2009)Screenshot from Twilight, Summit Entertainment (2008)

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Sources: 1, 2, 3, 4, 5


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