Actors whose careers were ruined by one role

Everyone makes mistakes—and that includes everyone who employs an army of agents, managers and publicists just to avoid mistakes. But when you're an A-list actor, your slip-ups are captured on film, projected six stories high and immortalized for criticism. As the instances listed here prove, all it takes is one box office bomb to tarnish a star.

Elizabeth Berkley in Showgirls (1995)

From 1989 to 1993, Elizabeth Berkley was brainy but semi-neurotic Jessie Spano in 75 episodes of Saved By The Bell. But when NBC canceled the series, Berkley (then 23) sought mature roles and found one in Showgirls—the only NC-17 movie ever widely released. Berkley won the part over a young Charlize Theron, but Showgirls tanked and incited brutal reviews. Berkley took home Razzies for "Worst Actress" and "Worst New Star" to go with the film's record 13 nominations and seven "wins" including Worst Picture and, eventually, Worst Picture of the Decade. Director Paul Verhoeven said Hollywood unfairly "turned its back" on Berkley, who quickly fell from big-budget features to Lifetime Original Movies. Although she's sporadically popped up in small parts on CSI: Miami, Law & Order: Criminal Intent and The L Word, it's not like you'd catch Charlize Theron on Dancing With the Stars. Berkley, however, finished sixth in 2013.

Freddie Prinze Jr. in Scooby-Doo (2002)

Freddie Prinze Jr.'s fame was a product of a time and place—that place being Hollywood, and that time being the 1990s. Back when movie studios were tripping over each other to put out teen slasher flicks and rom-coms, Prinze Jr. was a young man in high demand. He starred as Ray Bronson in 1997's I Know What You Did Last Summer and reprised the role in its 1998 sequel, then went on to cement his position as a Hollywood heartthrob with 1999's She's All That.


The new millennium brought a change in fortunes for the actor. While filmmakers were still keen to put out Prinze Jr.-fronted romantic comedies, audiences became less interested in seeing them. The actor starred in a string of critical flops in the first few years of the decade and decided to try something a little different, playing bleach-blond paranormal investigator Fred in the Scooby-Doo movie.


Despite a good showing at the box office, the 2002 adaptation of the classic Hanna-Barbera cartoon was panned by critics and left Prinze Jr. struggling for credibility, something he more or less gave up on when he returned for the film's 2004 sequel. The actor later revealed that he "didn't have fun" making either movie, and he abandoned Hollywood in the aftermath, pursuing passions elsewhere. He picked up work writing for the WWE and even took part in the odd storyline himself, though his career as a movie star has never recovered.


Alicia Silverstone in Batman & Robin (1997)

Everyone within a six-mile blast radius of Gotham felt the career aftershocks of Joel Schumacher's epically awful bomb Batman & Robin, but former Clueless darling Alicia Silverstone went from "Betty" to "Barney" faster than anyone. Her Razzie-winning turn as Batgirl to George Clooney's begrudging Batman helped spoil the release of Excess Baggage (the poorly received crime-comedy that was supposed to be her big starring vehicle) and promptly turned 1995's "It Girl" into 1997's has-been. Although Silverstone received an Emmy nomination in 2003 for her short-lived ABC series Miss Match and appeared in Beauty Shop, Batman & Robin foiled her chance at lasting stardom.

Taylor Lautner in Abduction (2011)

Thanks to the Team Jacob loyalists from The Twilight Saga, Taylor Lautner was once considered a breakout star in the making, and his name was attached to a slew of now-defunct blockbuster hopefuls—including a project with director Michael Bay, the long-awaited adaptation of Incarceron, and a live-action studio pic about Stretch Armstrong. Unlike Kristen Stewart and Robert Pattinson, who each endured their own critical and box office blunders after the supernatural romance series ended, Lautner wasn't as easily forgiven for his first high-profile flop.


In hopes of banking upon his werewolf popularity, Lionsgate quickly assembled attached Lautner to the mystery-action-whodunit pic Abduction, but the movie was a critical joke and certainly didn't justify the actor's asking price in the way of audience enthusiasm either. The movie was such a letdown that Lautner has since struggled to keep his name in the mainstream at all, living at the movie mercy of Adam Sandler, who cast him in small roles in Grown Ups 2 and The Ridiculous 6.


Nicolas Cage in Bangkok Dangerous (2008)

At this point, it might be hard to believe you need more than two hands to count the number of Certified Fresh films that Nicolas Cage has been involved in, but the vast majority of those successes came early in his career. The Oscar winner has settled for a life as a straight-to-VOD star in recent years, leaving fans and critics to wonder where it all went wrong.


Cage's career has been pockmarked with a long list of flops, but he always seemed to balance them with well-timed hits; his position as a credible A-lister really started to look seriously dubious after duds like 2006's The Wicker Man and 2007's Ghost Rider turned out to be huge letdowns. He had a brief reprieve with a successful (financially, at least) sequel to his fantasy epic National Treasure, but his next outing proved once and for all that his days of packing out movie theaters were behind him.


2008's Bangkok Dangerous couldn't even recoup its budget at the worldwide market, never mind domestically. A remake of the 1999 Thai film of the same name, it was pummeled by Rotten Tomatoes critics for "murky cinematography, a meandering pace, a dull storyline, and rather wooden performances." Bangkok Dangerous has an embarrassingly low 9 percent approval rating on the website, a trend which continued over the years and forced Cage to reexamine his career.


He told the Los Angeles Times in 2016 that he never wanted to become the new face of video-on-demand, but has decided to embrace it nonetheless. As he put it, "I think it's a good thing that at least these movies will be seen on some level and will not become completely extinct."


Demi Moore in Striptease (1996)

Demi Moore rose to prominence as part of the Brat Pack, an influential group of young actors who had the run of Hollywood in the mid-to-late '80s. A breakout star of the bunch, she went on to mold pottery opposite Patrick Swayze in 1990's Ghost, a surprise box office sensation that earned a staggering $500 million worldwide from a budget of just $22 million.


Moore remained a hot property throughout the early '90s, and by the middle of the decade she officially became Hollywood's highest-paid actress, agreeing to a record $12.5 million payday for 1996's Striptease. The erotic comedy tanked (opening behind The Nutty Professor, Eraser, and Disney's The Hunchback of Notre Dame) and Moore's reputation went down with it.


She had salt rubbed in her wounds at the Golden Raspberry Awards, where Striptease cleaned up, taking home six Razzies including Worst Picture. She was branded box office poison overnight, to the point that the Disney Corporation started sweating over the release of the Moore-led G.I. Jane, which they had already signed off on.


"We don't know what to do," one senior executive reportedly told Newsweek (via the Daily Telegraph). "People just don't want to see her. We would have to drag them kicking and screaming to see this movie." After G.I. Jane also failed to turn a profit, Moore receded from the spotlight, and eventually became better known for her marriage to (and divorce from) Ashton Kutcher.


Taylor Kitsch in John Carter (2012)

Taylor Kitsch almost became a pro hockey player at age 20, though injury forced him to reconsider his future. The Canadian told The National that he was forced to live rough after deciding to pursue a career in the movies, sleeping on subways in New York while he trained and then living out of his car in Los Angeles while trying to catch a break.


That break came when he won the part of running back Tim Riggins in Friday Night Lights. Kitsch gained a cult following during his time on the NBC football drama, which may have ultimately worked against him. Gawker argued the actor was "a victim of the Friends effect," claiming Kitsch fans didn't want to see him in tentpole roles, something the studios didn't count on.


In 2012—dubbed by Gawker "the year that Hollywood took a chance on Taylor Kitsch and failed miserably"—the actor fronted Disney's disastrous John Carter adaptation. The studio lost $200 million on the failed blockbuster, according to Forbes, and "John Carter" became another way to say "box office bomb." The disappointing performance of Battleship later that year proved to be the nail in Kitsch's coffin. "There is no doubt that a studio would think twice about casting him as a lead after the poor performances of both Battleship and John Carter," box office analyst Jeff Bock told Yahoo! Movies. "He might still be on the list, but pretty far down, and certainly not the A-list."


John Travolta in Battlefield Earth (2000)

John Travolta's story is one of multiple resurrections. His career has appeared dead and buried on several occasions, yet more than once, he managed to find ways to breathe new life into his career. He became one of the world's most recognizable movie stars after 1978's Grease, though by the mid-'80s his star had faded somewhat thanks to a string of poorly received pictures.


He shot back to the top at the turn of the decade after rom-com Look Who's Talking raked in an unexpected fortune (almost $300 million worldwide), though agreeing to appear in two sub-par sequels put Travolta right back where he started. It wasn't until the mid-'90s that he became relevant again thanks to Quentin Tarantino.


Pulp Fiction allowed Travolta to reinvent himself once more, and Tarantino even guided him down the right path afterwards, advising him to accept a part in Barry Sonnenfeld's Get Shorty. Two $100 million-grossing films followed (1996's Phenomenon and 1997's Face/Off), but poor choices over the next few years meant his career re-imploded with the millennium.


2000's Battlefield Earth was branded one of the worst movies ever made by The Guardian, and critics across the board agreed—the film has a pitiful 3 percent approval rating on Rotten Tomatoes. This drastically miscalculated L. Ron Hubbard adaptation cost $73 million to make and returned less than $30 million, sinking Travolta's career once more. Despite his best efforts, he's been unable to claw his way back since.


Tom Green in Freddy Got Fingered (2001)

It seems a lifetime ago that Tom Green was considered the next big thing in Hollywood. The Canadian funnyman actually dabbled in rap music as a teenager, going under the name MC Bones. Green was a member of Ottawa-based group Organized Rhyme, and only turned his attention to TV after they were dropped by their label.


According to The Guardian, Green returned to his parents' basement when the group disbanded and started developing his comedy act. Peddling his gross-out brand of comedy on cable access TV, he built a cult following that was eventually noticed by MTV. The network picked up The Tom Green Show in 1999, and it became popular enough to pique Hollywood's interest.


20th Century Fox jumped on the Green bandwagon and offered him the chance to write, direct and star in his own movie. The result was the surreal Freddy Got Fingered, a would-be comedy that debuted to withering critical scorn and ended its theatrical run as a bitter box office disappointment, just about recouping its budget but failing to turn a profit after marketing costs.


The rising star of the moment came crashing down to earth with a thump, and Green has been unable to recapture the public's interest since. Freddy Got Fingered has slowly earned cult status over the years (Vice called it "the most underrated film of all time"), but it's all too little, too late for Green.


Adam Sandler in Jack and Jill (2011)

Let's be real here. Adam Sandler has never really been a critical darling, but he did have a lot of fans who regularly went to theaters to watch his wacky antics for a long, long time…until Jack and Jill, that is. Thanks to his quotable comedic turns in movies like Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy, and Big Daddy, Sandler was riding high on a wave of followers who were willing to brave the theaters and home rental stores to see what he'd do in movies like The Longest Yard, I Now Pronounce You Chuck and Larry, Click, and You Don't Mess with the Zohan. Even critics had to give him credit for showing off some dramatic chops in Punch-Drunk Love and Funny People, and he had no trouble fronting ensemble efforts like Grown Ups and Just Go With It.


Jack and Jill, however, seemed to be the last straw for audiences who'd stuck with him through Little Nicky and The Animal. The movie is one of his most-hated projects of all time—even earning him a shelf full of Razzies—and turned audiences off of subsequent films like That's My Boy and Blended. Even Pixels, which was expected to tap into the same audience that loved similarly video game-themed hits like Wreck-It Ralph and The Lego Movie, bombed, and critics hated whatever was happening in The Ridiculous 6. Sandler burned audiences with Jack and Jill, and they've turned their backs on his subsequent work.


Halle Berry in Catwoman (2004)

After her Oscar-winning performance in 2001's Monster's Ball (and famously accepting a $500,000 bonus just to bare her breasts in Swordfish), Halle Berry could've had any role she wanted. Unfortunately, she wanted to play Catwoman. The 2004 Batman spinoff nearly swept the Razzies and Berry took most of the fallout with the Arizona Republic even suggesting she return her Academy Award. Instead, Berry returned to a diminishing role as Storm in the X-Men film series and has all but disappeared from leading roles.

Mike Myers in The Love Guru (2008)

If you ignore all the Wayne's World, Austin Powers and Shrek movies, Mike Myers' entire post-SNL résumé seems a lot less shagadelic. From So I Married an Axe Murderer and 54 through The Cat in the Hat, there were far fewer hits than misses. After the third Austin Powers and a five-year break from movies, Myers reemerged in 2008 with the universally hated comedy The Love Guru, which Roger Ebert called a "dreary experience." Myers took home a Razzie and apart from a cameo in one (previously filmed) scene in 2009's Inglorious Basterds and a few documentaries, he hasn't appeared onscreen since.

Neve Campbell in Wild Things (1998)

Neve Campbell was inescapable in the late '90s. A breakout star of the Golden Globe-winning series Party of Five, she almost single-handedly sparked the '90s horror revival with Scream and Scream 2, earning herself two consecutive Best Female Performance wins at the MTV Movie Awards, the cover of Rolling Stone, and an SNL hosting gig alongside musical guest David Bowie. But Campbell shed her good girl image (and most of her clothes) for the embarrassing erotic thriller Wild Things and although reviews were mixed, she never completely recovered. Campbell clung to the Scream franchise for two more sequels in 2000 and 2011, but otherwise toiled on studio clunkers like Three to Tango and second-rate indie flicks like When Will I Be Loved until resurfacing in 2016 for a part on House of Cards.

Jennifer Lopez in Gigli (2003)

A lot of people point to Gigli as the low point in Ben Affleck's career, but it's been even more damaging to the other half of the Bennifer brigade, Jennifer Lopez. Thanks to her breakout role in Selena and subsequent successes with Anaconda, Out of Sight, and Antz, Lopez had earned leading lady status in both rom-coms (like The Wedding Planner and Maid in Manhattan) as well as more serious film fare (including Enough, The Cell, and Angel Eyes) before Gigli came along. After that, she had a couple more shots in Shall We Dance and Monster-In-Law, but the trajectory she'd been on before was slowed significantly. She hasn't stopped working by any means—she lent her voice to the Ice Age animated movies, had a minor ensemble part in What to Expect When You're Expecting, and starred in the B-movie-at-best thriller The Boy Next Door—but her acting career has cooled substantially.

Chris Klein in Rollerball (2002)

In 1999, Chris Klein found both critical acclaim (for playing a sensitive jock in Election) and box office bank (for playing a sensitive jock in American Pie), then enjoyed a two-year run filled with romantic teen dramas (Here on Earth), blockbuster sequels (American Pie 2) and awards shows (named "Male Superstar of Tomorrow" at the Young Hollywood Awards). But then Klein strapped on elbow pads alongside LL Cool J for the dumbed-down Rollerball reboot (one of the costliest box office bombs ever) and the phone stopped ringing. Aside from Mel Gibson's We Were Soldiers (released less than a month after Rollerball), Klein appeared in just one movie (the underwhelming The United States of Leland) during the next two years. He released a steady stream of busts like Just Friends and Street Fighter, and his leading man potential had all but evaporated by the time his embarrassingly horrible Mamma Mia audition surfaced.

Lindsay Lohan in I Know Who Killed Me (2007)

Look. We could fill an entire article with the litany of other reasons why Lindsay Lohan's career has been so in the dumps in recent years, but you have to point to her 2007 flop I Know Who Killed Me as a pretty obvious turning point.


Before that film, Lohan was a true Hollywood starlet, even getting to share the screen with Meryl Streep in A Prairie Home Companion and Jane Fonda in Georgia Rule. She became a true teen sensation thanks to The Parent Trap, Freaky Friday, and Mean Girls, and her personal popularity landed her on the cover of countless magazines, for better and for worse. Her name was seen as a selling point when she led up this critically demolished mystery thriller, and its failure to attract an audience proved that those who knew her name may have been more interested in witnessing her tabloid-worthy behaviors than her screen presence. She went on to appear in Machete and the TV drama Liz & Dick, which caught some attention, but in the years since Killed Me, her screen appearances have been fewer and farther between.


Josh Hartnett in Lucky Number Slevin (2006)

Hartnett's late '90s hits (including The Faculty and The Virgin Suicides) made him something of a teen heartthrob. His turn as a swoony starcrossed lover in Here on Earth didn't do him any favors with critics, but his popularity soared and earned him top billing in a pair of big-budget actioners, Black Hawk Down and Pearl Harbor, and he returned to theaters in short succession with the rom-com 40 Days and 40 Nights, the eerie mystery romance Wicker Park, and the Frank Miller comics adaptation Sin City.


His fast-paced ascension hit a major speed bump, though, when he signed on to star in the title role of Paul McGuigan's Lucky Number Slevin, a star-studded caper that failed to impress fans or critics. With co-stars like Bruce Willis and Samuel L. Jackson, it had all the right ingredients to impress—but landed on Hartnett's shoulders when it failed. After that, he went on to star in the highly disfavored murder mystery The Black Dahlia and David Slade's underrated horror 30 Days of Night, but he has since had trouble reestablishing himself as the caliber of actor who enjoys co-leading status with the likes of Harrison Ford and Ben Affleck. You could argue that it was the buddy cop bomb Hollywood Homicide which issued Hartnett's initial career blow, but Slevin cemented the fact that he wasn't a bona fide movie star in the making.


Rebecca Gayheart in Jawbreaker (1999)

Rebecca Gayheart's jarring beauty and perplexing countenance made her something of a standout among the many scream queens of the '90s thanks to her appearances in back-to-back pop slashers Scream 2 and Urban Legends, and her turn in the TV teen drama Beverly Hills, 90210 only bolstered her fanbase. After her second major TV run in the short-lived Wasteland failed to take off, she turned back to the teen scene for the quirky dark comedy Jawbreaker.


The film was DOA with audiences and reviewers, however, and seemingly relegated her headshot to the B-movie pile forevermore. Her career has suffered a series of letdowns ever since, and while she might have been seen in this or that show along the way since then, she's never quite achieved the same star status others in her '90s peer group enjoyed.


Topher Grace in Spider-Man 3 (2007)

A year after he made an early exit from That '70s Show, Topher Grace had already put together an impressive movie résumé. From critically acclaimed performances in Stephen Soderbergh's Traffic and P.S. to starring roles in Win a Date With Tad Hamilton! and In Good Company, Grace seemed poised for full-time movie stardom. Then he signed on to play Venom in Sam Raimi's overwrought Spider-Man 3. Although the movie was still a blockbuster, Grace didn't exactly fit the ripped physical profile fans expected of Venom, and he was one of three villains battling for screen time. While Grace still found roles in Predators and Interstellar, Spider-Man 3 diminished his viability as a leading man.

Orlando Bloom in Elizabethtown (2005)

Orlando Bloom was a relative newcomer when he landed the role of unconquerable (and, let's face it, dreamboat) elf archer Legolas in The Lord of the Rings trilogy. Even though his long blonde locks and crystal blue eyes in the films were artificial for the movies, Bloom's natural aesthetic also earned him stud status, and he quickly nabbed the attention and hearts of millions outside of Middle-earth as well. His instant appeal earned him high-profile gigs, including the second swashbuckling lead in the Pirates of the Caribbean franchise, a similarly impressive billing stature in Wolfgang Petersen's pseudo-historical blockbuster Troy, and a respectable spot in Ridley Scott's cast for Black Hawk Down.


But then Elizabethtown happened. In theory, it's not a terrible idea for a guy who's been in so many large productions to dial it down a notch for a drama, but the movie flopped with critics and audiences alike, instantly undermining his acceleration to the A-list just as quickly as it had begun. The problem? His role and the film were charmless and altogether boring. Bloom starred in 2011's The Three Musketeers and has been able to fall back on his dual franchises to carry his film career forward with their endless barrage of prequels and sequels, but in recent years, his focus on smaller projects has made him harder to spot on the big screen—partly because he's also turned to the stage, making his well-received Broadway debut in a 2013 production of Romeo and Juliet.


Sean Connery in The League of Extraordinary Gentlemen (2003)

Nothing can actually ruin Sean Connery. The original James Bond through three decades, he repositioned himself in the '90s as a versatile action hero with The Hunt For Red October and The Rock. Despite flops like 1998's The Avengers and a Razzie-nominated performance in 1999's Entrapment, Connery still grabbed the title of People's "Sexiest Man of the Century" at age 69. In 2003, he returned as executive producer and star of The League of Extraordinary Gentlemen, adapted from Alan Moore's graphic novel series. While the movie debuted at No. 2, it finished the year at No. 44 (below even Kangaroo Jack) and received mixed reviews. Both shaken and stirred, Connery hasn't appeared in a movie since, officially announcing his retirement in 2005.

Colin Farrell in Alexander (2004)

In 2003, Farrell starred in a staggering four blockbusters (Daredevil, Phone Booth, S.W.A.T. and The Recruit). That track record inspired Oliver Stone to cast him as a bisexual Alexander the Great in his controversial 2004 epic Alexander. Critics hated the bloated movie and historians were offended by Stone's loose interpretation of facts, all while the movie made just $155 million against its $167 million budget. Farrell managed to dust himself off for a roles in Miami Vice, Pride and Glory, and Horrible Bosses, but he'll likely never have another year like the one before Alexander.

Hayden Christensen in Jumper (2008)

Star Wars fans had (and likely still have) a hard time accepting then-relative newcomer Hayden Christensen as their true Anakin Skywalker from the prequels Episode II and III, and it's partially because he suffered some notorious moments of bad acting throughout. (For instance, remember how much he hated the sand?) But the films were still staggeringly successful in the way of ticket sales, giving Christensen his shot at becoming the Next Big Thing in Hollywood.


That momentum was short-lived, however, because after he took on a little-seen but well-respected starring role in the fact-based newsroom drama Shattered Glass, he signed on for another perceived tentpole picture with 2008's Jumper. The sci-fi actioner, based on Steven Gould's popular novel series of the same name, was structured to launch a sequel series, but disappointed critics and underwhelmed audiences. The failure of that film marked the start of Christensen's mutual breakup with Hollywood, and he took several years off from show business shortly thereafter. He's since returned to making movies, but has been completely unable to capitalize on the momentum he lost after finishing his stint on The Dark Side.


Emile Hirsch in Speed Racer (2008)

Emile Hirsch became something of an indie sensation in the early 2000s after he appeared in a succession of critically lauded films including Lords of Dogtown, Into the Wild, and Milk, but those accolades didn't translate to box office gold the way Speed Racer filmmakers the Wachowskis hoped it would. It failed to make back its own production budget—let alone launch a franchise as anticipated.


It also put a major damper on the Hollywood heat Hirsch accrued through his lower-budget releases. He's since been unable to regain that early momentum, and even releases that have enjoyed some respect, like Killer Joe and Lone Survivor, found him in supporting roles. Hirsch remains admirably active—he shot three movies in 2016—but the industry doesn't seem to be in any rush to put him back behind the wheel of a major motion picture.


Kevin Costner in Waterworld (1995)

At one point, Kevin Costner was one of the biggest movie stars in the world. He put together a string of huge successes in the '80s, including The Untouchables, Bull Durham, and Field of Dreams; by the time he won dual Oscars for directing and starring in Dances with Wolves, he was one of Hollywood's most bankable household names. Even The Bodyguard, which didn't fare well with many reviewers, was a massive box office hit.


When Costner put his clout behind the high-concept dystopian actioner Waterworld, though, he ended up over his head. A notorious production nightmare that barely made any money due to its engorged budget, it took a critical flogging that sent Costner down a path of many pans to come. While 1996's Tin Cup was a charming enough dramedy, it still failed to excite audiences, and his next would-be blockbuster, 1997's The Postman, brought out even fewer viewers and was roundly panned by critics. Costner's star status was officially jeopardized. One flub is forgivable, but two in quick succession? Disastrous.


It's been hit or miss for Costner since then. High-profile efforts like Message In a Bottle and For Love of the Game were met with lukewarm critical and commercial receptions, but dramas like Thirteen Days, Open Range (which he also directed), and The Upside of Anger served as low-key reminders of the gifts that helped make him a a star. Costner's more recent efforts include supporting roles in blockbusters like Man of Steel and Jack Ryan: Shadow Recruit, but his marquee status never really recovered after Waterworld.


Cuba Gooding, Jr. in Boat Trip (2002)

Cuba Gooding, Jr. rose to fame in 1991 as the lead in Boyz n the Hood—a movie so important that it's in the National Film Registry. He went on to win an Oscar for his work in Jerry Maguire and continued rolling with As Good as It Gets, What Dreams May Come and Men of Honor. In 2002, however, he unleashed his first two starring vehicles: the family comedy Snow Dogs and the offensively horrible comedy Boat Trip. Both were critical disasters, but at least Snow Dogs made money. With his credibility blown, Gooding only made things worse with later Razzie-nominated roles in Radio, Norbit, and Daddy Day Camp. Of the 18 movies he released between 2008 and 2013, all but five went straight to DVD.

Geena Davis in Cutthroat Island (1995)

Between 1986 and 1992, Geena Davis went from being a model-turned-actress to an Oscar-winner (for 1988's The Accidental Tourist) and a bona fide box office commodity with The Fly, Beetlejuice, Thelma & Louise, and A League of Their Own. Then in 1995, Davis teamed with her husband, director Renny Harlin, for the swashbuckling Cutthroat Island, which cost $98 million to make and pulled in just $10 million, giving it the notorious distinction of the all-time worst financial loss by a movie. Davis and Harlin tried again with the moderately successful The Long Kiss Goodnight in 1996, but for the next decade, Davis only appeared on the silver screen twice (in 1999's Stuart Little and 2002's Stuart Little 2) and despite winning a Golden Globe in 2006 for ABC's Commander in Chief, the series only lasted as long as 2000's The Geena Davis Show: one season.

Warren Beatty in Town & Country (2001)

Warren Beatty took Hollywood by storm in 1967 with the colossal hit Bonnie and Clyde (which he also produced), and he became one of his generation's true renaissance men by directing and starring in Heaven Can Wait, Reds, Dick Tracy, and Bulworth. Although he had endured his share of box office bombs like Ishtar and Love Affair, none of them suffered the spectacular failure of 2001's Town & Country. One of the most expensive flops in film history, the romantic comedy made back just $10 million of its $90 million budget, and Beatty didn't take another project for 15 years.