Once you’re a big star in Hollywood, they say you’ve got your pick of all the great roles. Unfortunately, history has proven that even the biggest stars sometimes have a little trouble predicting what’s going to be a hit and what’s going to be a flop.

Here are just some examples of actors turning down really great movies, and opting instead to do films they definitely came to regret.

20. Will Smith turned down The Matrix for Wild Wild West

Before Keanu Reeves was cast as Thomas Anderson/Neo in the Wachowskis’ groundbreaking 1999 sci-fi action smash The Matrix, a number of other big-name stars were considered for the role. These included Brad Pitt, Nicolas Cage, Val Kilmer, Sandra Bullock (yes, really) and a certain Will Smith, who passed on the role to instead make blockbuster misfire Wild Wild West.

Smith has long since admitted that turning down Neo to play Jim West was one of his biggest career mistakes, but he has also said that he wouldn’t have done as good a job in the role as Keanu Reeves did.

19. Sylvester Stallone turned down Romancing the Stone for Rhinestone

In the early 80s, Sylvester Stallone was at the height of his fame when he was offered the role of Jack T. Colton in the romantic comedy-adventure Romancing the Stone. Instead, the Italian Stallion chose to make musical comedy Rhinestone with Dolly Parton. This, Stallone has since confessed, was a very bad decision, as Rhinestone bombed at the 1984 box office, whilst Romancing the Stone was a smash with Michael Douglas playing Colton opposite Kathleen Turner.

Rhinestone proved to be an embarrassing blip on Stallone’s early 80s resume. However, he bounced back in a big way in 1985, with back-to-back blockbusters in Rocky IV and Rambo: First Blood Part II.

18. Tim Roth turned down Harry Potter for Tim Burton’s Planet of the Apes remake

British actor Tim Roth found himself to be in demand around the turn of the millennium. He was the first choice to play the part of Professor Quirrell in Harry Potter and the Philosopher’s Stone (aka Sorcerer’s Stone), the first instalment in what was hoped to be a major franchise. Roth passed in order to take the part of the villainous Thade in director Tim Burton’s 2001 reboot of Planet of the Apes, which was also hoped to kickstart a series. Ian Hart was cast as Quirrell after Roth turned the part down.

Needless to say, it was Harry Potter that proved the bigger hit by far in 2001, successfully launching one of the most popular film franchises of all time. 2001’s Planet of the Apes, meanwhile, was widely dismissed as a mistake all around.

17. Michael Madsen turned down Pulp Fiction for Wyatt Earp

After making a big name for himself with the role of Vic Vega/Mr Blonde in Reservoir Dogs, Michael Madsen was offered the lead role of Vincent Vega (implied to be the brother of the Reservoir Dogs character) in writer-director Quentin Tarantino‘s next film, Pulp Fiction. Madsen declined in order to take the role of Virgil Earp in fact-based western Wyatt Earp, alongside Kevin Costner in the title role.

Tarantino cast John Travolta as Vincent Vega instead, and on top of rejuvenating Travolta’s career, Pulp Fiction also proved to be one of the most acclaimed films of the 1990s. Wyatt Earp, meanwhile, is almost entirely forgotten, not least because 1993’s Tombstone tackled the exact same story to greater success.

16. Emily Blunt turned down Iron Man 2 for Gulliver’s Travels

Although 2010’s Iron Man 2 is often regarded a lesser entry from the early days of the Marvel Cinematic Universe, the film introduced a character who came to be a major player in the franchise: Natasha Romanoff, aka Black Widow. While Scarlett Johansson wound up playing the role, the first choice for the part was Emily Blunt – but she pulled out due to a scheduling clash with Gulliver’s Travels, a largely forgotten Jack Black vehicle based on the classic story.

Although Blunt missed out on a role that Johansson reprised seven times (including in her own upcoming standalone Black Widow movie), the English actress insists she has no regrets. The rumour mill has since linked Blunt to the part of Sue Storm in Marvel’s planned Fantastic Four reboot, but she has dismissed this, stating that superhero films “are not up my alley.”

15. Kevin Costner turned down The Shawshank Redemption for Waterworld

There aren’t too many actors who have enjoyed such a meteoric rise and spectacular fall as Kevin Costner. By the early 90s, the actor was at the top of his game after an unprecedented string of hits – and around this time he was asked to play the role of Andy Dufresne in Stephen King adaptation The Shawshank Redemption. Costner passed, as he was committed to playing the heroic Mariner in fantasy adventure Waterworld.

Costner’s Bull Durham co-star Tim Robbins would play Andy instead, and while The Shawshank Redemption was only a modest hit on release, today it’s widely considered one of the greatest films ever made. Waterworld, by contrast, was a notoriously troubled misfire that sullied Costner’s reputation, and soon thereafter his superstar days were over.

14. Mel Gibson turned down Gladiator for The Patriot

2000 sword and sandals action epic Gladiator made Russell Crowe a superstar. The New Zealand-born actor’s turn as Maximus Decimus Meridius landed him the Best Actor Oscar, and pretty much overnight he became one of the most in-demand leading men around. Things could have been rather different, however, if the role had been accepted by a certain other actor from Down Under who was offered it first: Mel Gibson.

Reportedly, Gibson passed on Gladiator as (at 44) he considered himself too old for the part. Instead, he took the lead in another violent historical drama, The Patriot, which earned him a then-record $25 million payday, but was otherwise met with a comparatively lukewarm response.

13. Harrison Ford turned down Cape Fear for Regarding Henry

While director Martin Scorsese and his long-time collaborator Robert De Niro were in development on their 1991 remake of classic thriller Cape Fear, De Niro personally approached Harrison Ford to ask him to co-star in the film. Ford was interested, but only if he was allowed to play the menacing Max Cady and De Niro played opposite him as the mild-mannered Sam Bowden.

Needless to say, De Niro didn’t like that idea, so Ford turned the film down. Instead, 1991 saw Ford appear in largely forgotten drama Regarding Henry, which did middling business critically and commercially. Cape Fear wound up a considerably bigger hit, with De Niro as Cady and Nick Nolte in the good guy role that Ford declined.

12. Bruce Willis turned down Ghost for The Bonfire of the Vanities

Bruce Willis had quickly become one of the hottest stars in Hollywood in the late 80s after his breakthrough hit Die Hard. However, when the actor was offered the role of Sam Wheat in supernatural romance Ghost, he declined, reportedly feeling the material was a bit corny. This didn’t stop Willis’ then-wife Demi Moore from signing on to play female lead Molly, with Patrick Swayze ultimately accepting the role of Sam.

Willis instead took the part of Peter Fallow in The Bonfire of the Vanities, director Brian De Palma’s adaptation of the Tom Wolfe novel, which went down like a lead balloon with critics and audiences. By contrast, Ghost wound up the biggest box office smash of 1990, and for a time was the third highest-grossing film ever made.

11. Matt Damon turned down Avatar for The Bourne Ultimatum

In the mid-2000s, Matt Damon was approached by James Cameron with an offer to take the role of Jake Sully in the writer-director’s long-in-development sci-fi epic Avatar. Damon turned him down, in part because he wasn’t sure the film would work, but also because the shooting schedule clashed with his commitment to The Bourne Ultimatum, the third film in the spy series. With Damon out of the running, Cameron cast the largely unknown Sam Worthington.

It would be wrong to write off Jason Bourne as a bad role, and we can respect Damon’s commitment to his signature franchise. Still, this was a major financial miss for the actor, as Avatar went on to become the biggest hit in box office history. The real sting is that Damon had been offered 10% of the film’s gross profits, which – assuming the film performed as well with him in the lead – would have left him more than $290 million better off, and comfortably the highest-paid actor of all time. (Sam Worthington didn’t get that same deal, incidentally.)

10. Brooke Shields turned down Scarface for Sahara

Brooke Shields rose to prominence as a child star and model in the late 70s, which seemed to set the stage for a strong career in mature roles. One of the first distinctly adult roles Shields was first offered was Elvira Hancock in Scarface, a remake of the 1932 gangster movie from leading man Al Pacino and director Brian De Palma.

On the advice of her mother, Shields declined, instead accepting the lead role in period adventure movie Sahara. Scarface wasn’t a huge hit in 1983, but it’s long since been re-assessed as a classic; Sahara, meanwhile, bombed on release and is all but forgotten today. Michelle Pfeiffer took the role Shields turned down, and it helped make her a superstar.

9. Molly Ringwald turned down Pretty Woman for Betsy’s Wedding

After her performances in Sixteen Candles, The Breakfast Club and Pretty in Pink, Molly Ringwald was the quintessential 80s teen movie icon and a prominent member of the ‘Brat Pack.’ Unfortunately, Ringwald had a little difficulty crossing over from teen roles to adult roles. One project that promised to help her do so was 3,000, an edgy drama about prostitution.

However, whilst 3,000 was in development, the script underwent significant rewrites, making it a romantic comedy. Uncomfortable with the tone and subject matter, Ringwald dropped out. Julia Roberts would take her place, and the film became Pretty Woman. It proved a massive hit, whilst Ringwald’s next project – the Alan Alda film Betsy’s Wedding – disappeared without a trace.

8. Eddie Murphy turned down Rush Hour for Holy Man

After rising to superstardom in the early 80s as a movie star and stand-up comedian, Eddie Murphy’s career began to cool off somewhat in the 90s. Then he was offered a movie that might have made him red-hot again: Rush Hour, an action-comedy that would have cast Murphy as an LA detective teamed up with a Hong Kong cop played by Jackie Chan.

Murphy decided against this, instead taking the lead role in satirical comedy Holy Man. Alas, that film proved a critical and commercial disaster, whilst Rush Hour was a big hit that went on to spawn two sequels, and helped make a star out of Murphy’s replacement Chris Tucker in the process.

7. Jennifer Connelly turned down Heathers for Etoile

Jennifer Connelly started out as a child model before making a big impression as an actress in Once Upon a Time in America and Labyrinth. Hollywood expected big things from Connelly, and so she was at the top of the wish list for the lead role in a new, edgy teen comedy entitled Heathers.

Ultimately, Connelly decided against making Heathers, instead agreeing to star in Italian gothic melodrama Etoile. While that film was poorly received and quickly forgotten, Heathers soon became a cult classic and helped establish leading lady Winona Ryder as one of the definitive Generation X superstars.

6. David Schwimmer turned down Men In Black for Since You’ve Been Gone

David Schwimmer was at the height of his Friends fame when he was offered the role of Agent J, the ambitious young cop who finds himself recruited to a secret law enforcement agency policing extra-terrestrials in Men in Black. Although it had ‘blockbuster’ written all over it, Schwimmer declined the role.

Instead, Schwimmer directed and starred in comedy-drama Since You’ve Been Gone, in which he cast all his old friends from the Chicago theatre. With Will Smith as J, Men in Black proved a massive hit and spawned a long-running franchise, whilst Since You’ve Been Gone inspired so little confidence from studio Miramax they wound up releasing it as a TV movie.

5. Mickey Rourke turned down Pulp Fiction for F.T.W.

For all his notable successes, the career history of Mickey Rourke is littered with ill-advised missteps. After turning down such 80s hits as Beverly Hills Cop, The Untouchables and Platoon, Rourke was offered the chance of career redemption when he was offered a plum role in Pulp Fiction: Butch, the prize fighter (a role Rourke could relate to, having been a pro-boxer himself).

Rourke, in his infinite wisdom, turned down writer-director Quentin Tarantino and instead made F.T.W., a crime drama that Rourke himself co-wrote. Of course, F.T.W. (AKA The Last Ride) came and went without anyone noticing, whilst Pulp Fiction became one of the most acclaimed hits of the 1990s and reinvigorated the career of Bruce Willis, who took the role once earmarked for Rourke.

4. Tom Cruise turned down Footloose for All The Right Moves

We tend to think of Tom Cruise as an actor who couldn’t put a foot wrong back in the 80s. However, in the wake of his breakthrough lead performance in 1983’s Risky Business, Cruise made another movie that threatened to undo that good work: All the Right Moves, a trite high school sports drama that attracted far less audience interest.

To make matters worse, in taking the lead in All the Right Moves, Cruise had turned down another movie that proved a considerably bigger hit: Footloose, the dance drama which would ultimately star Kevin Bacon. Still, while that was a black mark on Cruise’s record, he didn’t have much to worry about, as soon enough 1986’s Top Gun made him the biggest star of his generation.

3. Christina Applegate turned down Legally Blonde for Just Visiting

In 2001, Christina Applegate was still best known for the role of Kelly Bundy on sitcom Married… with Children, which had ended just four years earlier. Keen to avoid typecasting, Applegate decided against taking the lead role of Elle Woods, fashion student turned aspiring lawyer in comedy Legally Blonde.

Reese Witherspoon signed on instead, and Legally Blonde proved a huge hit, earning widespread acclaim and spawning a sequel. Meanwhile, Applegate’s 2001 movie Just Visiting – a remake of a French comedy about dim-witted knights transported to the modern-day – was met with poor reviews and low box office receipts.

2. Leonardo DiCaprio turned down American Psycho for The Beach

Leonardo DiCaprio had just headlined the biggest film in box office history, Titanic, when he became aware that Lionsgate Films were developing an adaptation of Bret Easton Ellis’ controversial novel American Psycho. He was eager to take on the lead role of Patrick Bateman, but there was a problem: director Mary Harron wanted the comparatively unknown Christian Bale.

After briefly being attached to star, DiCaprio ultimately chose to walk away from American Psycho to instead make The Beach with director Danny Boyle. As American Psycho is now considered a classic and The Beach was a comparative flop, this might seem a misstep; however, many have applauded DiCaprio for recognising that Bale was the right actor for the role, not him.

1. Katie Holmes turned down The Dark Knight for Mad Money

Having risen to fame on 90s TV drama series Dawson’s Creek, Katie Holmes embarked on a movie career in the 2000s, and enjoyed her highest-profile role as Rachel Dawes in the blockbuster superhero movie Batman Begins. When work began on sequel The Dark Knight, it was known that the character of Rachel would return, so it was assumed Holmes would too.

However, for reasons which have never been made entirely clear, Holmes opted against reprising the role and backed out of The Dark Knight to instead make Mad Money, a crime comedy that barely made a dent at the box office. Maggie Gyllenhaal took over as Rachel Dawes, and The Dark Knight became one of the biggest hits ever at the time, as well as earning massive critical acclaim.