18 Celebrities Who Passed on Roles and Now Live with Regret

In the entertainment world, scoring the role of a lifetime is like striking gold. However, not all glittering opportunities lead to golden careers, and sometimes, the best move is the one not made. Today, we’re looking at 18 people who turned away once-in-a-lifetime roles, for better or for worse.


Dave Chappelle as Benjamin Buford “Bubba” Blue in “Forrest Gump”

Editorial credit: Kathy Hutchins / Shutterstock.

Dave Chappelle turned down the role of Bubba in “Forrest Gump,” thinking the movie would flop. Sure, he’s good at comedy, but it seems like his fortune-telling skills could do with a little work! The film went on to become a beloved classic, and Chappelle missed out on sharing screen time with Tom Hanks.


Molly Ringwald as Vivian Ward in “Pretty Woman”

Editorial credit: Ron Adar / Shutterstock.

The queen of ’80s teen movies, Molly Ringwald, could have been the star of “Pretty Woman.” However, she passed because she thought the role wasn’t the right fit, which allowed Julia Roberts to become the iconic Cinderella of Hollywood Boulevard. We’re pretty sure Ringwald regretted this, given that Roberts’ career skyrocketed after the film’s release.


Matt LeBlanc as Phil Dunphy in “Modern Family”

Editorial credit: Kathy Hutchins / Shutterstock.

Can you picture Joey from “Friends” as the lovable goofball dad Phil Dunphy? Yeah, neither can we. Matt LeBlanc was offered the role but he thought he wasn’t the right guy for the job, and honestly – we have to agree. Ty Burrell stepped in and turned Phil into one of the most beloved TV dads ever.


Jon Stewart as Host of “Meet the Press”

Editorial credit: Darwin Brandis / Shutterstock.

Before Chuck Todd, studio executives approached Jon Stewart to lead “Meet the Press.” However, Stewart felt that mixing his satire with the show’s serious tone might not be the best fit. He stuck with “The Daily Show,” leaving us to wonder, “What if?” However, it seems like it was the right decision, as “The Daily Show” continues to be successful even today.


Emily Blunt as Black Widow in the Marvel Cinematic Universe

Editorial credit: Kathy Hutchins / Shutterstock.

Emily Blunt was the first choice for Black Widow but had to bow out due to scheduling conflicts with Gulliver’s Travels. Scarlett Johansson then slipped into the iconic black suit, becoming one of the MCU’s most beloved characters. Despite this near-miss with the MCU, Blunt built a versatile career spanning drama to musicals and so much more.


Jerry Seinfeld as a Replacement for Johnny Carson on “The Tonight Show”

Editorial credit: Nounpusher Photography / Shutterstock.

Who knew that late-night TV could have been very different? Jerry Seinfeld almost took over “The Tonight Show” after Johnny Carson, but, ultimately, it wasn’t to be. Instead, Jay Leno took the reins, and Seinfeld continued his reign as a sitcom king. Although it was the right decision, we’re curious to know what his version of “The Tonight Show” might have looked like.


Leonardo DiCaprio as Anakin Skywalker in “Star Wars”

Editorial credit: Andrea Raffin / Shutterstock.

Leonardo DiCaprio almost became  Anakin Skywalker, but he wasn’t ready to dive into the galaxy far, far away. Instead, Hayden Christensen took up the lightsaber and became the Anakain we all know and love. Of course, this decision hardly affected DiCapriom, as he later became one of Hollywood’s most respected actors.


Sandra Bullock as Neo in “The Matrix”

Editorial credit: Fred Duval / Shutterstock.

In a twist of fate, Sandra Bullock almost took on Neo in “The Matrix” when producers were thinking about gender-swapping the character. However, Keanu Reeves took the red pill, and the rest is cyberpunk history. It’s hard to imagine Bullock dodging bullets in slow motion, but maybe in a parallel universe, she’s the One.


Will Smith as Neo in “The Matrix”

Editorial credit: Featureflash Photo Agency / Shutterstock.

Likewise, before Keanu Reeves, Will Smith had the chance to choose between the red and blue pill. Smith turned it down to star in “Wild Wild West,” a decision he’s later said was probably not his best. The Matrix might have had a few more one-liners, but Smith decided to battle mechanical spiders instead!


Madonna as Trinity in “The Matrix”

Editorial credit: Denis Makarenko / Shutterstock.

Here’s another what-if from “The Matrix”! This time, the Queen of Pop, Madonna, was going to appear in an undisclosed role. Madonna has never actually revealed who she was meant to be in the movie, just that she regrets turning it down. Rumor has it that she was going to play Trinity, who was later played by Carrie-Anne Moss.


Dana Delany as Carrie Bradshaw in “Sex and the City”

Editorial credit: Kathy Hutchins / Shutterstock.

Dana Delany was once offered the role of Carrie Bradshaw, but she passed because she wasn’t keen on doing a series about sex. So, Sarah Jessica Parker then stepped into Carrie’s shoes, turning the column into a cultural phenomenon. We’ll never know how Delany’s version would have been different, but Parker’s Carrie became the voice of a cosmopolitan generation.


John Travolta as Forrest Gump in “Forrest Gump”

Editorial credit: Andrea Raffin / Shutterstock.

John Travolta had the chance to sit on that famous bench and tell the world about chocolates, but he said no to “Forrest Gump.” Honestly, we can’t really imagine him taking on such a serious role, as we’re pretty sure he would’ve made it unintentionally hilarious. It’s hard to imagine anyone else making us feel quite as much at home on that bench.


Beyoncé as A Star in “A Star Is Born”

Editorial credit: Tinseltown / Shutterstock.

Before Lady Gaga, Beyoncé almost starred in the remake of “A Star Is Born.” However, due to various production delays and her own busy schedule, she stepped aside, leaving Gaga to take on the role. We’re sure Queen Be must be jealous, as Gaga ended up earning critical acclaim for her performance. 


Angelina Jolie as Ryan Stone in “Gravity”

Editorial credit: Tinseltown / Shutterstock.

Angelina Jolie missed out on the opportunity to play Ryan Stone in “Gravity.” Honestly, we can’t blame her – this was a seriously challenging role! It was a physically and emotionally intense role, as it required the actor to show a range of emotions almost completely in isolation, floating in the silent vacuum of space. Later, Sandra Bullock was chosen as the one to fly it solo.


Nicolas Cage as the Green Goblin in “Spider-Man”

Editorial credit: Andrea Raffin / Shutterstock.

Nicolas Cage passed on the chance to portray the Green Goblin. It was a role that demanded a complex blend of menace and madness as Spider-Man’s enemy. We can’t really imagine anyone else but Willem Dafoe bringing this character to life with his twisted sense of humor and dramatic flair.


Michelle Pfeiffer as Catherine Tramell in “Basic Instinct”

Editorial credit: Andrea Raffin / Shutterstock.

Apparently, Michelle Pfeiffer turned down the role of Catherine Tramell because it was a pretty daring and provocative character. She’s not wrong! Sharon Stone’s portrayal became legendary, combining seductive charm with a chilling depth. All these years later, that interrogation scene is just as controversial as it was back then!


Julia Roberts as Leigh Anne Tuohy in “The Blind Side”

Editorial credit: Everett Collection / Shutterstock.

Once upon a time, Julia Roberts had the opportunity to play Leigh Anne Tuohy, a woman whose family adopts a homeless teenager, guiding him to become a professional football player. Critics praised Sandra Bullock’s performance for its warmth and strength, which eventually won her an Oscar. We’re sure Julia Roberts is kicking herself still!


Al Pacino as Captain Willard in “Apocalypse Now”

Editorial credit: Patryk Kosmider / Shutterstock.

For “Apocalypse Now”’s Captain Willard, Al Pacino was going to explore the darkness of the human soul against the backdrop of the Vietnam War. However, Martin Sheen later took on the intensely demanding and harrowing role. The movie has often been cited as one of the greatest movies of all time, so we’re sure Pacino regrets it.

Share Article:

William Tyler

Writer & Blogger

William Tyler is a prolific movie writer hailing from the vibrant state of Florida. Growing up amidst the lush landscapes and diverse communities of the Sunshine State, Tyler developed a deep appreciation for storytelling from an early age. With a knack for crafting captivating narratives and memorable characters, Tyler’s screenplays captivate audiences with their blend of heart, humor, and insight. Drawing inspiration from the unique experiences and colorful personalities he encountered in Florida, his work reflects a deep connection to the region’s culture and identity.

Leave a Reply

Join the family!

Sign up for a Newsletter.

You have been successfully Subscribed! Ops! Something went wrong, please try again.
Edit Template