Career Killing Roles That Actors Should Have Passed On

Hollywood success is fleeting. One day you are accepting an Academy Award and the next you can’t even get an audition. With one bad film, these stars saw their careers turn sour.

How does an Academy Award winner see his career in a tailspin? For Cuba Gooding Jr., it took starring in the homosexual stereotype-riddled Boat Trip. Gooding Jr. is not that far removed from his award-winning role as Rod Tidwell in Jerry Maguire too, yet, between 2008 and 2013 13 of his 18 films were released straight to DVD. A sad turn of events for Tre Styles of Boyz N The Hood, a film preserved by the National Film Registry.

A big payday doomed Demi Moore’s career. Moore used her recent successes in A Few Good Men  and Ghost to receive $12.5 million to star as Erin Grant in Striptease. Although the movie was a commercial success, critics panned Moore’s dramatic performance as clashing with the comedic supporting characters. Moore’s follow-up, G.I. Jane attracted more attention due to Moore shaving her head for the role than her performance itself. Trying to keep up with Moore today? She will appear in Empire season 4.

Hollywood has a tendency to place its biggest stars together with the hope that they will bring out the best in each other. When the star-studded Lucky Number Slevin failed, it took Josh Hartnett’s career with it. Hartnett went from teen heartthrob to afterthought within a decade. While he and his co-stars Bruce Willis, Ben Kingsley, and Morgan Freeman navigated the choppy timeline, the film fought Pulp Fiction comparisons that it could not match and that Hartnett himself could not survive.

While he will always be known for his roles in Troy, The Lord of the Rings trilogy, and the Pirates of the Caribbean films, Orlando Bloom can’t seem to draw the parts that he used to. Bloom’s career almost took a turn for the worst after starring in Cameron Crowe’s Elizabethtown. The film could not capture Crowe’s past magic and left audiences bored. Following Elizabethtown, Bloom was able to save himself by reprising his franchise-famous roles as Legolas and Will Turner.

Between 1987 and 1994 there were not many bigger stars than Kevin Costner. He was capable of playing and directing a variety of successful characters but was yet to dabble in science fiction. His efforts to make gains in the genre fell flat. Waterworld and Postman, released with two years of each other, ended his run at the top. After the expensive Waterworld could not meet expectations, Costner’s last gasp in Postman failed miserably, barely grossing $18 million on an $80 million budget.

Alicia was a budding star following her performance as Cher Horowitz in Clueless. The coming of age comedy showcased Silverstone’s charm and earned her a multi-million dollar deal with Columbia-TriStar. Clueless has since become a classic, but what happened to Silverstone? She joined Warner Brothers’ Batman and Robin as Batgirl. The film’s effort to lighten the typically dark franchise failed miserably, and Silverstone’s career never recovered. A few direct to video films followed, and she never again matched Clueless‘s success.

Between Saturday Night Live, Austin Powers, and Shrek, audiences are very familiar with Mike Meyers’ crazy collection of characters and voices. For two decades Meyers rode his talents to hilarious hits, that is until 2009’s The Love Guru. Whereas Wayne Campbell and Austin Powers silliness still resonates today, Guru Pitka relied too heavily on crude humor and turned Meyers into a “once was.” Outside of the Shrek moneymakers, Meyers’ projects seem to have dried up.

Did you know Will Smith acted alongside his son Jaden in a film outside of 2006’s The Pursuit of Happiness? How could you forget M. Night Shyamalan’s After Earth? Frankly, the film is precisely so – forgettable. History would predict Smith plus science fiction to be a winning formula (i.e. Men in Black, Independence Day), yet Smith calls it “the most painful failure” of his career and rightfully so. What’s more agonizing? Sitting through any of his next films.

To any child, the chance to watch Star Wars is privilege enough. The chance to star in it? That is the opportunity of a lifetime. For Jake Lloyd, it was a Hollywood death sentence. The first prequel, released 16 years after Return of the Jedi, failed to meet expectations and brought a lot of stress to young Jake. Kids teased him at school, and promotional interviews exhausted him to the point he quit acting altogether.

Colin Farrell started to rack up a reputation for blockbusters after 2003. Daredevil, Phone Booth, SWAT, and The Recruit all put Farrell front and center to millions of moviegoers. With one choice, Farrell almost erased his goodwill. Oliver Stone’s Alexander rubbed everyone the wrong way: critics, historians, Greeks, and Iranians. With Farrell in the middle of it all, he barely came out alive. Thankfully, he attached himself to Michael Mann’s Miami Vice adaptation and has not slowed down as a leading man.

How the mighty have fallen. At the turn of the century, Halle Berry was THE leading woman. She won an Academy Award for Monster’s Ball, co-starred in X-Men, and became a Bond girl. Berry’s dip into the DC Comics world set her career back, however. Catwoman never allowed Berry to show off her award winning acting chops, rather focusing on sexualizing her instead. She now settles for marginalized X-Men roles and the occasional rom-com.

Without Lori Petty, Keanu Reeves would never have learned to surf in Point Break, and Geena Davis would never have had a sister to trade away in A League of Their Own. Petty’s career started off a solid note but took a sharp turn with sci-fi comedy Tank Girl. The film lost $21 million, and Petty has not received any roles with top billing. She has recently found a home as a recurring character on Orange is the New Black.

Child stars always struggle to maintain their juvenile successes as they age. It’s a standard career trajectory, but Lindsey Lohan, for a time, appeared to break away from the mold. Lohan’s career finally gave way to the stereotype after 2007’s I Know Who Killed Me. In the midst of dealing with her personal demons, the psychological horror film sealed her fate. The film received a then-record of Razzies for worst film of the year, and Lohan’s leading roles dissipated.

Reviving a beloved film is always an arduous task. Reviving a beloved film without any of its original stars is an impossible task. Regrettably, Jamie Kennedy tried to fill Jim Carey’s patent leather shoes and bright white smile to no avail. The Son of the Mask tanked and took Kennedy with it. He was a successful stand-up and was applauded for his roles in the Scream films and the Jamie Kennedy Show until this disaster made him untouchable.

Fran Drescher captivated television audiences for years as The Nanny. Although she is known for her TV work, her film work is responsible for her downfall. As The Nanny‘s run came closer to an end and her popularity rose, Drescher began appearing in movies. The Beautician and the Beast was an epic failure, and Drescher never recovered. Her life took an even greater turn with a cancer diagnosis in 2000. She is now in remission.

Italian actor Roberto Benigni struck a chord with audiences in his brilliant and award-winning performance in Life is Beautiful. The image of him climbing on top of his seat at the 1999 Academy Awards after the film’s win continues to endure and endear. So where did he disappear to? Benigni starred and directed Pinocchio to the content of Italian audiences and the dismay of North American ones. He would only appear in four more films.

Sure, Adam Sandler has never been a critical success, but his frat boy films are comedy gold and gave him the capital to green-light his own projects. By 2008 Sandler had already shifted away from the crude humor he specialized in and moved towards family comedies. Audiences tolerated films such as Grown Ups and Bedtime Stories, but critics never bought in. 2011’s Jack and Jill brought the worst of out Sandler’s idiosyncrasies. His next films only followed in its terrible footsteps.

The world opened its arms to 12-year-old Natalie Portman due to her work in Leon: The Professional. After two Star Wars prequels, Hollywood closed its doors to her. Before she became an Oscar winner, Portman portrayed Padme Amidala. The first prequel received so much backlash that its actors became toxic and, Portman included, could not land work. Thanks to a reference letter from director Mike Nichols, she got a supporting role in Cold Mountain and never looked back.

For a time it appeared as if Taylor Lautner was on the path to stardom. Twilight‘s Team Jacob movement propelled Lautner into the public eye and starring roles. He first starred in Abduction, a decision he might want to take back. The film was destroyed by critics, one of whom who wrote that an “actual abduction may be preferable.” Beyond Twilight sequels, Lautner attached himself to Adam Sandler’s disastrous The Ridiculous 6 and is yet to appear in another major studio film.

Hardcore Star Wars fans will always have an issue with the prequel trilogy. Hayden Christensen’s Anakin failed to meet their standards, and his acting failed to lift the character. Regardless, the films performed incredibly well at the box office, and Christensen was positioned to make a continued impact on Hollywood. Instead, he chose Jumper, a film expected to launch a sequel series based on the novels, which lacked charisma, could not match the hype and derailed his career.

Ever since Christopher Reeve tossed his red cape and blue tights aside, Warner Bros. wanted to reboot the Superman brand. Initially looking into big names to fill the roll, director Bryan Singer insisted on an unknown actor, similar to Reeve’s casting. Routh signed on to the role and two future films, but it was a massive disappointment. He never escaped the stigma of mishandling his enormous opportunity and has not landed any other notable roles.

Chris Kattan became a fan favorite during his 7 years on Saturday Night Live for his wonky characters like Mr. Peepers and Mango. While his head-bobbing Butabi Brothers (with Will Ferrell) led to a feature film, Kattan had hoped to shed his SNL shackle and make his way into films with Corky Romano. Instead, the film tanked due to its lack of imagination and good jokes. Kattan went on to make small appearances until he landed a steady role in ABC’s The Middle in 2009.

By the early-90s, Rebecca Gayheart began converting her modeling career into an acting career. With small parts in television series in her pocket, Gayheart first received attention as Luke Perry’s love interest on Beverly Hills, 90210. She capitalized on the moment and turned roles in Scream 2 and Urban Legend into a starring role in Jawbreaker. Jawbreaker barely made $3 million, and Gayheart’s career nosedived into B-movie obscurity. Her last credit was in 2013’s G.B.F.

Before George Clooney became a bona fide superstar, he owned primetime tv as Dr. Doug Ross on ER. As he sought to expand his profile beyond television, he took what should have been a career-shaping role as Bruce Wayne, but almost killed it completely. Clooney’s Batman came off as unspirited and never carried the film as he should have. He would eventually be okay, settling into the role of Danny Ocean, and receiving multiple Oscar nominations.

Chris Klein’s career got off to a promising start thanks to some solid acting in Election and hearty box-office returns in American Pie. Although most people know him as “Oz” from the American Pie series, Klein worked on enough projects to be considered for leading roles. Klein surely would take a mulligan on his first leading effort in Rollerball. The film lost near $45 million and never lived up to the original. Klein has since released a constant flow of busts.

Another actor touched by the superhero curse. Topher Grace became a welcomed face to fans of That 70’s Show. Grace left the show to focus on a film career which started out well. Acclaimed supporting roles led to more starring roles. He signed on to Spider-Man 3 hoping the film would replicate the success of the first two installments. The film did well, but Grace could not fit the physical expectations of Venom. He still secures film roles, but without the juice he once carried.

Geena Davis took advantage of her opportunities as pushed herself away from modeling and into acting. She had a golden touch between 1986 and 1992, catapulting herself to stardom and an Oscar. Davis then pushed forward on the much-maligned Cutthroat Island with her then-husband and director Renny Harlin to catastrophic results. The film lost almost $90 million, which is the worst financial loss ever by a film (adjusted for inflation). She would not star in a feature film for another 15 years.

Debates over Al Pacino versus Robert DeNiro have circulated for years. When the two famed stars finally showed up in a scene together in Heat (DeNiro only appeared in Godfather flashbacks), it was cinematic magic. Their second attempt did not fair as well. Righteous Kill fell flat on all accounts once viewers moved past the awe of seeing them together. Outside a Golden Globe nomination for Danny Collins seven years later, Pacino’s work has significantly suffered and slowed.

Emile Hirsch found himself in the middle of a wave of praise for his work in Milk, Into the Wild, and Lords of Dogtown. His portrayal of Christopher McCandless gave the world a look at a dedicated actor as he lost 40 pounds for the role. Hirsch signed up for Speed Racer hoping to bring his indie dedication to a major production. Instead, the film could not make back its expensive production costs, and Hirsch scaled his work back to lower budget films.

The Party of Five and Scream star was a late 90s staple. She hosted Saturday Night Live, appeared on the cover of Rolling Stone, and won a handful of MTV award. Campbell took on a different role in 1998’s Wild Things. Shedding her good girl image, Neve teamed with Kevin Bacon and Matt Dillon for the erotic thriller. Beyond a couple of Scream sequels, Neve could no longer land the roles that made her a star in the first place.

What do you get when you try to make a film adaptation out of a Disney World attraction? A $17 million loss and a tainted career. Christopher Walken’s storied career may include an Academy Award, but it also includes The Country Bears. His career has never looked the same. For every Wedding Crashers and Catch Me If You Can that followed, he can’t seem to shake Gigli, Click, Balls of Fury, and Kangaroo Jack.

Peak “Bennifer” was a prosperous time for Jennifer Lopez and Ben Affleck. That good fortune would instantly disappear with their joint project Gigli. Lopez’s movie career had matured and offered her a handful of leading roles, including one with her then-beau. Gigli was a categorical failure for both, stunting Affleck’s own career for a time, and knocking J-Lo (the actress) back down to earth. She would continue to act, but without the pace and success she had once upon a time.

Sequels are always a dicey proposition for established stars. Sharon Stone’s second go at Basic Instinct failed to live up to the first thanks to constant production delays and comparison to its predecessor. Stone never reestablished her mojo from the 1992 original, or her Oscar-nominated performance in Casino. She is still hopeful that a third installation will receive a green light and she can work as the director. 25 years later, Stone does not resonate with audiences the way she used to.

Baby boomers salivated at the chance to see Warren Beatty, Diane Keaton, and Goldie Hawn together in Town and Country. What they received instead was an unrelatable and expensive romantic comedy. No one could forget Beatty in Bonnie and Clyde, but could only hope to forget this dismal production. $80 million in losses later, Beatty was clearly scared by the epic failure. He would not make another film for 15 years until he played Howard Hughes in Rules Don’t Apply.

John Travolta’s career is a tale of peaks and valleys. Unfortunately, he currently sits in his second deep slump after the career-ruining Battlefield Earth. Travolta was in high demand in the 90s thanks to a Pulp Fiction bump. The sci-fi action film is considered one of the worst films ever made, only banking $30 million in ticket sales against $73 million in production costs. Travolta’s dream for future films died with the first one, as did his second wind.

You probably remember Elizabeth Berkley from her role as the independent and intelligent Jessie Spano on NBC’s Saved By The Bell. For four seasons, Berkley roamed the halls of Bayside High School, but do know what she did after the show? Unlike many of her cast members, she did not appear in the many spinoffs. Berkley has been reduced to a guest star on various network dramas since bombing in the controversial Showgirls. Although it’s become a cult hit recently, it was universally crushed by critics.

The Batman universe suffered severely following Batman and Robin. Chris O’Donnell happily signed on to reprise his role as Robin, but the film killed his movie career. The doomed film came only a few years after O’Donnell turned heads with his performance in Scent of a Woman. Although he never headlined another major movie, O’Donnell found a home on television 12 years later as the co-star of NCIS: Los Angeles alongside LL Cool J.

For Matthew McConaughey to reach the McConaissance, he needed to fall hard first. McConaughey’s career got off to a hot start thanks to his role in Dazed and Confused. He cooled down until settling into a string of romantic comedies. Rock bottom came in the form of the straight to DVD Tiptoes. Both McConaughey and Gary Oldman struggled to escape its shadow. They both recovered, and McConaughey would go on to win an Oscar.

Eddie Murphy ruled the 80’s comedy scene. As the title character in The Adventures of Pluto Nash, a sci-fi action comedy, Murphy and the movie failed so miserably that it only made $7 million worldwide against a $100 million budget. He seldom appears as a lead actor today.

James Bond himself could not have stopped this unenthused effort from reaching audiences. The League of Extraordinary Gentlemen brought numerous literary characters together without the inspiration and exposition that propelled them in the first place. Connery was stuck leading the charge regrettably. The film was Connery’s last on-screen appearance in an impressive 50 year long career. It is too bad he rode off into the sunset with the stench of this film. Hopefully he can bounce back.