The 50 Worst Decisions in Movie History

The first two Deadpool movies could hardly have been more successful. The 2016 Ryan Reynolds movie and the 2018 sequel grossed over $1.5 billion combined. And fans and critics loved nearly everything about them, including the pivotal decision to dramatically up the gore and swear word count from your typical Marvel film, even if that meant accepting an R rating. A third one is coming soon featuring the return of Hugh Jackman as Wolverine. It’s almost guaranteed to be a smash. But the series nearly died before it even launched. They first rolled out Ryan Reynolds as Deadpool in the 2009 flop X-Men Origins: Wolverine. You may not remember that since it’s an off-brand version of the character where he’s not wearing the red suit and mask. And in a move that still baffles no matter how many times they’ve tried to explain it, his mouth is sewn shut, making it impossible for the character to spout his trademark quips. Most of the time, it’s a stunt double as opposed to Reynolds himself. There isn’t a single thing about this version of Deadpool that works on any level. It’s so dumb that the first two Deadpool subtly mock it several times, culminating in a mid-credit sequence in the second movie where he travels back in time to the time of X-Men Origins: Wolverine to snuff the character out of existence. 

When George Lucas headed off to the deserts of Tunisia in 1976 to film the original Star Wars, Hollywood paid little attention. He’d proven his value as a director with 1973’s American Graffiti, which was enough for 20th Century Fox to sign off on his space project, but even they had no clue that he was about to change the film industry forever. They just hoped to receive a return on their investment. And when he offered to exchange his $500,000 salary in exchange for the merchandise and sequel rights, they gladly agreed. They simply couldn’t imagine a future for Star Wars lunch boxes, action figures, toy lightsabers. They certainly didn’t think that new Star Wars movies and television shows would still be coming out nearly 50 years later. In 2012, George Lucas sold his Star Wars rights to Disney for $4 billion. By that time, the franchise had grossed somewhere in the ballpark of $20 billion when you factor in merch. All that cash could have gone to Fox had they simply told Lucas to keep his lousy $500,000.

Richard Pryor is undoubtedly one of the greatest stand-up comedians in history. But with the lone exception of a few projects, like Stir Crazy and Brewster’s Millions, he made really lousy movies. The low point came in 1982 when he starred in The Toy where he plays a desperate man that gets “purchased” by a rich father, played by Jackie Gleason, to serve as a plaything to his spoiled son. The creative team behind this movie, including Superman director Richard Donner, surely had good intentions. But this is essentially a movie about a slave. It’s also painfully unfunny for a supposed comedy. “Donner, with his embarrassingly bad direction, manages to suck dry the talents of everyone involved,” reads a review in the Austin Chronicle. “[It is] one of the worst comedies ever to emerge from a major studio.” Donner made Goonies just three years later. It’s as perfect as The Toy is horrid. It also manages to create jokes that don’t remind viewers of the most horrific chapter in American history.

This may surprise people that lived through it, but 1999 is now regarded by movie buffs as one of the greatest years in Hollywood history. It’s the year that gave us Fight Club, Magnolia, The Matrix, Election, Office Space, South Park. Bigger Long and Uncut, The Blair Witch Project, Boys Don’t Cry, The Sixth Sense, The Virgin Suicides, Galaxy Quest, Being John Malkovitch, The Talented Mr. Ripley, and too many other classics to list here. (Check out Brian Raftery’s book Best. Movie. Year. Ever.: How 1999 Blew Up the Big Screen to learn more about it.) When the Academy Awards handed out Best Picture that year, however, they went with American Beauty. This seemed like a very profound work of cinema at the time, but try watching it again. It revolves around Kevin Spacey desperately trying to have sex with his teenage daughter’s best friend. We’re supposed to think there’s deep meaning behind a plastic bag blowing in the wind. There’s a whole gay panic plot with the evil guy next door. It’s hard to get through any random five minutes without cringing. Giving it Best Picture in any given year seems nuts today, but it’s especially insane when you look at the other choices they had. 

Ask a young movie fan to name the worst Marvel movie and you’re likely to hear about Iron Man 2, Thor: The Dark World, Ant-Man and the Wasp: Quantumania, or The Eternals. Those with slightly longer memories will likely reference Spider-Man 3, Blade: Trinity or Elektra. But anyone with a deep reservoir of knowledge won’t hesitate. They’ll immediately call out Howard the Duck and end the debate. The 1986 movie, produced by George Lucas, centers around an alien from Duckworld that travels to Cleveland, Ohio. He befriends a young Lea Thompson, nearly has sex with her in one of the most disturbing moments in cinema history, and battles the Dark Lord of the Universe. It’s supposedly a comedy, but the laughs never really come. There’s also the small problem that Howard the Duck himself is way creepier than the filmmakers intended. He’s an expressionless hellbeast that will haunt your dreams. The movie was a complete bomb that proved George Lucas isn’t infallible. It was another 22 years before Iron Man came along and showed the industry how to do this Marvel thing properly. 

On July 18th, 2019, the first trailer for Cats appeared online. Within seconds, people on Twitter had difficulty focusing on anything else. There were many questions. How could the “digital fur” applied to all the actors via CGI look this shitty? Why do the female characters have human-like breasts without nipples? Where are their genitals? Why do their tails look like they’re coming out of the wrong part of their bodies? Why do I feel like I’ve just journeyed into some ghastly corner of Hell? It turns out the creative team behind the movie had many of these same questions. The “digital fur” was a nightmare to create and they didn’t have the time to get it right. They worked furiously right up until the premiere date, and even added improvements after the movie hit theaters, which is almost unprecedented in movie history. There are many, many other problems with Cats, which is why it has a 19% on Rotten Tomatoes, but it was hard for anyone to focus on any of them when it just looked so shitty and disturbing.

Imagine you’re Michael Oher. You earned millions of dollars playing eight seasons in the NFL. Nearly everyone you meet knows the incredible story of your life, especially the part about being brought in by the wealthy Tuohy family as a teenager, and sent to a fancy private school that helped you secure a spot at the University of Mississippi. That might sound pretty great. Now imagine that they made a movie about your life that portrays you as a Forrest Gump-like simpleton with borderline magical powers that didn’t know how to even play the game of football until you were taught by Sandra Bullock and a little kid moving around ketchup bottles on a table. Imagine that movie grossed $300 million and played on TV all the time. Imagine if everyone believes that it tells the 100% true story of your life. That would drive you pretty nuts, right? “People look at me, and they take things away from me because of a movie,” Oher said in 2015. “They don’t really see the skills and the kind of player I am. That’s why I get downgraded so much, because of something off the field.” Oher eventually filed a lawsuit against the Tuohys, claiming they unfairly denied him profits from the movie and lied about adopting him. (They strenuously object to his charges.) Regardless of who is right and wrong, there’s no doubt The Blind Side has caused Michael Oher a lot of pain. Would it have been so hard to portray his life accurately?

Mel Gibson’s biblical epic The Passion of the Christ was one of the biggest movies of 2004, grossing $612 million worldwide. The film focuses on the final days of Jesus’ life, culminating with a brutal crucifixion scene. Before it even came out, Jewish organizations were concerned it would spread the myth that Jews were responsible for Christ’s death. “The Passion of the Christ” continues its unambiguous portrayal of Jews as being responsible for the death of Jesus,” the ADL wrote in a statement. “There is no question in this film about who is responsible. At every single opportunity, Mr. Gibson’s film reinforces the notion that the Jewish authorities and the Jewish mob are the ones ultimately responsible for the Crucifixion…We do not know what is in [Mel Gibson’s] heart. We only know what he has put on the movie screen.” Two years later, the world learned exactly how Gibson felt about Jews when he was arrested for drunk driving. “”Fucking Jews,” he said to the arresting officer. “The Jews are responsible for all the wars in the world.” If there was any doubt Gibson harbored antisemitism in his heart, it vanished in that moment.

The original Alien launched Ridley Scott as a titanic force in Hollywood, paving the way for Blade Runner and everything that followed in his career. James Cameron was given the reins of the franchise for Aliens, demonstrating he could handle a big budget movie after proving himself with The Terminator. For Alien III in 1992, the studio handed control to director David Fincher. He spent the Eighties shooting music videos for Madonna, Sting, Pala Abdul and many other superstars, and they felt he was finally ready to make a movie. But the project had major script problems from the beginning and went through many incarnations during pre-production. The studio began to fear their untested director couldn’t handle the project. They hated his initial cut, insisted on reshoots, and then created a new edit without his consent. The movie was still a major disappointment. Fincher looks back on it as one of the worst times of his career, and said it nearly caused him to quit the business entirely. Thankfully he stuck around and gave the world Seven, Fight Club, The Social Network, Gone Girl, and many other masterpieces. In other words, the man knows how to make a movie. Who knows what could have happened had he been allowed to execute his vision for Alien 3 without studio meddling?

On December 31, 2006, the New York Times ran an article headlined ‘Mike Myers: Intentional Man of Mystery.’ The man himself wasn’t interviewed for the piece, which presented him as a mysterious genius prone to long absences from the public sphere until he reemerged with a brilliant new franchise like Wayne’s World, Austin Powers, or Shrek. They note that his next movie centered around a “love guru” from India. “In 2005 the character made his debut on some small theater stages in Greenwich Village, just as his Austin Powers persona was once honed at Los Angeles nightspots,” the Times writes. “Unrecognizable in makeup, a white wig and a yogi’s long flowing beard, Mr. Myers — who called himself Pitka — dispensed wild advice to the audience in a thick Indian accent.” In other words, he had a truly terrible idea for a new character that would involve him dressing up as an Indian. He had the sense not to wear brownface, but that’s the only saving grace of 2008’s Love Guru, which roped in co-stars Justin Timberlake and Jessica Alba. It’s a painfully unfunny movie that did tremendous damage to his career. Crazy as it sounds, it was the last time he had the lead role in a movie. His film work over the past 15 years has been entirely in animation, documentaries, and supporting roles. There’s been loose talk of Austin Powers 4 and even hopes of a Wayne’s World 3 (at least in the minds of fans), but nobody is talking about The Love Guru 2. There never should have even been a Love Guru 1.

In a fair world, Orson Welles would have been given the freedom to make whatever movies he wanted for the rest of his life after Citizen Kane. It was his very first movie, he was just 24, and it’s inarguably one of the greatest films of all time, if not the very greatest. But in this universe, the movie was a flop, and it ruffled the feathers of some absurdly powerful people. This was also a time when the studios, not directors, were the major forces in Hollywood. Directors were seen as replaceable cogs in the movie machine. And so when Welles adapted Booth Tarkington’s 1918 novel about a wealthy family at the turn of the century, he didn’t have final cut. When the studio didn’t like his version of the movie, they simply pushed him aside, and took a hatchet to his hard work. They chopped out nearly an hour, added in a happy ending, and even lost a ton of footage. There have been re-edits in recent years based on original Welles notes, and even an attempt to animate what was lost, but it’s impossible to recreate what could have been. It’s gone forever. Sadly, this wasn’t the last time Welles would face this sort of issue throughout his career.

Turning Pearl S. Buck’s 1931 book The Good Earth into a movie was a good idea. It’s about a Chinese family living in a small village in the Anhui province that was a huge bestseller in the early days of the Great Depression. It taught Americans a lot about day-to-day life in rural China, and many historians argue that it helped Americans sympathize with China against Japan at the start of World War II. Where they erred in making the film adaptation–and this is a biggie–was casting white Americans in all of the lead roles. They wore yellowface makeup. It’s just about as cringy as you can imagine. In the years that followed, the studio tried to argue they wanted to use Chinese actors, but felt that Americans “weren’t ready” for such a movie. They also tried to blame the Hays Code for forcing them not to have any characters in mixed-race relationships. Whatever the truth, it’s time for a remake with an actual Chinese cast.

At the end of the 2017 Academy Awards, Warren Beatty and Faye Dunaway walked up to the podium to hand out the award for Best Picture. Beatty pulled the supposed winning name out of a red envelope, looked a bit dumbfounded, peeked back in to see if something else was hiding in there, and then started to speak in a very halting fashion. “And the Academy Award…for best Best Picture…” He stopped himself, unsure of how to proceed since he was staring at a slip of paper that said Emma Stone wins Best Actress for La La Land. A frustrated Dunaway then glanced at the paper and said La La Land into the mic. The next two and a half minutes were absolute chaos, offstage and off, since representatives from PricewaterhouseCoopers, who were tasked with passing out envelopes and making sure the right names were read, totally froze. Stage manager Gary Natoli eventually took matters into his own hands by going onto the stage and telling the La La Land Producers that Moonlight actually won. Beatty and Dunaway were handed the wrong envelope. This was the first Academy Awards after Donald Trump won and it added to the sense that the world was breaking down, and nothing was working like it should.

The story of studios compromising the visions of ambitious directors and chopping down their movies is nearly as old as Hollywood. Orson Welles had to deal with this indignity for the vast majority of his career. The sad reality is that studios usually have the final say over the final cut of their movies. The directors work for them. The most egregious example of studio butchery in Hollywood history took place in 1984 when Sergio Leone’s crime epic Once Upon a Time in America, starring Robert DeNiro, Joe Pesci, James Woods, and Elizabeth McGovern was cut from four hours and 29 minutes to two hours and 19 minutes. They also rearranged the scenes in a way that made the movie unwatchable. “Relationships are truncated, scenes are squeezed of life, and I defy anyone to understand the plot of the short version,” Roger Ebert wrote. “The original Once Upon a Time in America’ gets a four-star rating. The shorter version is a travesty.” There have been numerous attempts over the years to restore Once Upon a Time in America to its original form, though most Americans have only seen the truncated one. That’s a tragedy since this movie deserves to be mentioned in the same breath as The Godfather and Goodfellas. If the studio had just trusted Leone and allowed his version of the movie to hit theaters back in 1984, history would have unfolded very differently.

Whoopi Goldberg comedies, buddy cop action flicks, and sci fi films about dinosaurs generated a ton of money back in the Nineties. But if you mash up Sister Act, Bad Boys, and Jurassic Park, you wind up with the ungodly horror that was 1996’s Theodore Rex. If you aren’t familiar with this particular piece of celluloid history, it takes place in a freakish future where police officers and anthropomorphic dinosaurs in tennis shoes work together to solve crime. If you think this sounds like a dumb concept for a movie, you are not wrong. Goldberg realized this herself after verbally agreeing to shoot the film and tried to wiggle out of it, leading to a lawsuit and ultimate salary of $7 million. But she was practically shooting the movie with a gun to her head, and it shows in every frame. The budget eventually swelled to $33 million even though Theodore Rex is just a guy in a cheap rubber suit straight out of the TV show Dinosaurs. The studio eventually learned they’d made a horrible mistake and dumped it straight to VHS. At the time, it was the most expensive straight-to-DVD film in Hollywood history. All these years later, “Theodore Rex” has become Hollywood shorthand for “really, really, really dumb idea.”

In the early years of Hollywood, films that depicted unrepentant criminality, philandering spouses, and drug addiction were commonplace. But once talkies arrived and theaters spread all over the nation, calls for government censorship began growing louder and louder. (Remember, this was a somewhat puritanical time when alcohol was illegal nationwide.) Before the government had any chance to pass laws censoring movies, the studios decided to simply do the job themselves by establishing The Hays Code. Simply put, it severely limited what filmmakers could put on the screen. Once they began to strictly enforce the code in 1935, movies changed in significant ways. Anyone that committed an “immoral act” needed to be punished before the end of the picture. There couldn’t be even a hint of sexual activity, even between happily married characters. You couldn’t mock the Christian faith in any way, and you couldn’t show “mixed race” couples or homosexuality. The list goes on and on. Clever filmmakers found subtle ways around it, but it still forced huge creative compromises on nearly every movie. It wasn’t lifted until 1968 when ratings entered the picture, ending the need for such rigid self-censorship.

Some of the best movies in Hollywood history are remakes. That’s even true in the case of 1939’s The Wizard of Oz, which was actually the third attempt to adapt L. Frank Baum’s book into a motion picture. But if you’re going to create a movie that’s already been attempted, you want to make sure you’re telling the story in a new and interesting way. And if a perfect version of the movie already exists, you need a really compelling reason to revisit it. Gus Van Sant didn’t follow either of these unwritten rules in 1998 when he decided to film a shot-for-shot remake of Alfred Hitchcock’s Psycho with Vince Vaughn, Julianne Moore, and Viggo Mortensen as a cinematic experiment nobody was asking to see. This was right after Good Will Hunting, when Van Sant could have gotten the go-ahead to make any movie he wanted, which made his decision to make Psycho all the more baffling. It is simply not possible to improve on the original. And creating a virtual carbon copy does little but inspire unflattering comparisons. “The movie is an invaluable experiment in the theory of cinema,” Roger Ebert wrote in a brutal one-a-half star pan, “because it demonstrates that a shot-by-shot remake is pointless; genius apparently resides between or beneath the shots, or in chemistry that cannot be timed or counted.” In other words, what the hell was anyone thinking when they thought this was a good idea?

It’s easy to forget that Star Wars was aimed at children from the very beginning. The original trilogy had R2-D2, C-3PO, Ewoks, and many other characters designed to delight young people and make for great toys. And when George Lucas returned to the Star Wars universe in the late Nineties to create The Phantom Menace, he felt he had to create another character that children could latch onto. Unfortunately, he went with a dundering, oafish, Gungan named Jar Jar Binks that speaks in broken English and felt uncomfortably like a crude Jamaican stereotype. Here are some sample Jar Jar words of wisdom: “Dissen ganna be bery messy!,” “How wuude!” and “Whaten dey speaking?” Lucasfilm felt that Jar Jar would be the breakout character of the film and they created mountains of Jar Jar merchandise. We even put him on the cover of Rolling Stone. But critics didn’t care much for Jar Jar, Kids didn’t care much for Jar Jar, and Star Wars fanatics really, really didn’t care for Jar Jar. They even created an entirely new version of the movie where his dialogue was dubbed over with the words of a wise elder. Lucas got the memo and virtually erased the character from the sequels, but the damage was done. Jar Jar Binks has become a symbol of everything wrong with the prequels. (To be fair, they look pretty good today when compared with the latest batch of sequels.)

Judy Garland was just sixteen-years-old when she signed on to play Dorothy Gale in The Wizard of Oz. But even at that young stage in her life, she was very familiar with the brutal expectations of Hollywood, especially when it came to remaining rail-thin and working 18-hour days. To get through it all, the studio gave her a nearly-toxic assortment of barbiturates and amphetamines designed to wake her up in the morning, fall asleep at night, and keep off any excess weight. It didn’t take long for her to become hopelessly addicted. The brass at MGM couldn’t have possibly cared less. They just wanted their star to keep working. But the pills took a terrible toll on her body. She was just 47 when she died, but looked about 20 years older. The tragedy could have been avoided if only the Hollywood studio system of the Thirties and Forties cared even a little about the health of their stars.

After creating Jaws, Close Encounters of the Third Kind and Raiders of the Lost Ark in a period of just six years, most studio heads would have been happy to let Steven Spielberg do whatever he wanted for this next project. But when he approached Columbia CEO Frank Price with the idea for E.T., he decided to pass, thinking that a story about a kindly alien that bonds with a small boy would only appeal to children. They sold the script to MCA for a million dollars and five percent of the profits. The movie, of course, was a colossal success, grossing nearly $800 million. A few years later, the studio had similar doubts about Back to the Future and let that one go too. The dunderheaded streak continued in the early Nineties when they shot down Pulp Fiction. Before either of those things could happen, Price left Columbia for a new role at Universal. One of his first major projects? Howard the Duck.

Judging pop cultural creations of the past through the prism of the present can sometimes be unfair. Standards change over time and jokes that once landed without a hint of controversy are now seen as deeply offensive. It doesn’t mean the people making them were terrible. They just came of age in a different era. But we’re only willing to take this line of reasoning so far. Some things are so egregiously offensive that “but it was the past!” simply doesn’t cut it as an excuse. A great example is Mickey Rooney’s portrayal of Japanese photographer/landlord I. Y. Yunioshi in Breakfast at Tiffany’s. Casting Rooney as an Asian character was bad enough, but he wore face makeup, a prosthetic mouth piece, and spoke broken English in a thick, cartoonish accent. It’s impossible to imagine a stereotype more obnoxious and crude. It’s so wildly offensive that it basically ruins an otherwise wonderful film. Also, this wasn’t 1931. It was 1961. They should have known better. ​​And even the press of the time took note. “Mickey Rooney gives his customary all to the part of a Japanese photographer,” wrote the Hollywood Reporter, “but the role is a caricature and will be offensive to many.” That is quite the understatement.

As Mel Brooks proved with The Producers in 1967, there’s nothing wrong with making a funny movie about Hitler and the Nazis. Roberto Benigni proved it’s even possible to make a comedy about the Holocaust itself with 1997’s Life Is Beautiful. That movie collected three Academy Awards for that one, including Best Actor. But it requires a very delicate touch and the right tone. Jerry Lewis, the man behind The Disorderly Orderly, The Nutty Professor, and Boeing Boeing, was not the best man for this job. He tried in 1972 with The Day the Clown Died where he played a German clown that winds up escorting Jewish children into the gas chambers of Auschwitz. The movie never actually came out because screenwriter Joan O’Brien wouldn’t sign off on the final product. The movie instantly gained legendary status as the single worst idea for a movie in Hollywood history. Bits of the movie have surfaced over the decades, but there’s reportedly not even a complete negative anywhere in the world. That’s probably for the best.

By the turn of the millennium, John Travolta was one of the most successful actors in Hollywood. That fact would have stunned anyone back in 1993 when Look Who’s Talking Now hit theaters (that’s the one where the dogs talk), but he followed that one up with a little movie called Pulp Fiction. He then made Get Shorty, Michael, Face/Off, A Civil Action, Phenomenon, Primary Colors, and other big movies in quick succession. This gave him enough juice to finally actualize his dream of turning L. Ron Hubbard’s 1982 novel Battlefield Earth into a motion picture. This was a transparent attempt to spread the gospel of Scientology via the nation’s multiplexes, even though Travolta’s team denied it every time the subject came up. “I’ve never even dealt with or talked to the church on this,” Travolta’s manager said. “This is an action-adventure, science-fiction story. Period. The movie has nothing to do with Scientology.” This was, of course, a complete crock of shit. That might have been somewhat excusable if Battlefield Earth was a good movie, a decent movie, or even a middling movie. But it’s a terrible movie. Every second of it is agony. It’s hard to imagine a single person converting to Scientology because of it. They were too busy falling asleep or laughing at the ridiculous sight of John Travolta with dreadlocks. It won eight Golden Raspberry Awards and the Worst Picture of the Decade award in 2010. If earth sticks around long enough for the Golden Raspberry Awards to hand out a “worst movie of the century” at their 2100 ceremony, it’ll probably win that too.

It’s not hard to understand why the team behind 1981’s Roar felt they had to use real lions on the set of their 1981 movie Roar. The plot of the Noel Marshall/Tippi Hedren/Melanie Griffith revolves around an American family that moves to a nature preserve in Tanzania to study lions. This was years before CGI and putting humans in lion costumes was just out of the question. They’d look as phony as the apes in Planet of the Apes. What is impossible to understand is why they felt using actual wild lions, as opposed to trained, domestic ones, made even the tiniest bit of sense, and why the studio and their insurance company signed off on this psychotic scheme. Marshall was bit by a lion so hard at one point that he nearly lost his arm. Griffith was virtually scalped in a vicious attack that required 50 sutures. Nearly every member of the cast and crew was attacked at one point, and accounts from the set read like a real-life horror movie, but they somehow decided to just keep forging ahead. The topper is that movie was an enormous box office dud. Few people today have ever heard of Roar. But the unlucky few that worked on that set will never, ever forget it.

In 1947, 33 years before he became president, and when he still considered himself a Democrat, Ronald Reagan testified before the House Un-American Activities Committee. He was the president of the Screen Actors Guild at the time, and they wanted to know if communists had infiltrated the organization. “There has been a small group within the Screen Actors Guild which has consistently opposed the policy of the guild board and officers of the guild, as evidenced by the vote on various issues,” he said. “That small clique referred to has been suspected of more or less following the tactics that we associated with the Communist Party…I have heard different discussions and some of them tagged as Communists.” That was all the committee needed to hear. It was the start of a horrible chapter in Hollywood history in which the government was hunting down suspected communists, and anyone tagged as one would basically be unable to work for the next decade. It caused enormous damage to the careers of many good people, including Charlie Chaplin, Langston Hughes, Dalton Trumbo, and Lena Horne.

The original Home Alone grossed nearly $500 million on a budget of just $18 million. It’s become a Christmas standard beloved by generations of children, and it launched a franchise that continues to this day. For 20th Century Fox, this was the dream scenario when they took on the film back in 1990. But every single cent could have gone to Warner Bros. They were the original studio attached to the movie during production, but they balked when director Christopher Colmbus said he needed $17 million to finish it. They told him they weren’t willing to go higher than $14 million. Unwilling to cut corners, the Home Alone team–including screenwriter John Hughes– figured out a way to wiggle out of the deal and get 20th Century Fox to give them the money they needed. Making matters worse, Warner Bros. had to watch Bonfire of the Vanities go down in flames at this exact same time. “There is little cheer at Warner Brothers today,” read a year-end article in the New York Times. “While many Americans refused to spend money on last-minute Christmas gifts, they were no more willing to fill those idle hours by going to ‘Bonfire of the Vanities.’ [The movie] cost about $40 million to produce and more to promote, but it took in a paltry $3.1 million in its opening weekend.” Meanwhile, Home Alone was shattering box office records. Not a great Christmas for the Warner Bros. team.

The tragedy on the set of the 1983 movie Twilight Zone that killed Vic Morrow and two child actors has been the subject of much debate and legal action over the past four decades. Sticking solely to undisputed facts, the accident occurred during the shooting of the “Time Out” segment where a man travels back in time to the Vietnam War and needs to protect two Vietnamese children. Director John Landis hired 7-year-old Myca Dinh Le and 6-year-old Renee Shin-Yi Chen for the roles even though he didn’t file the legal paperwork required for them to appear on camera. During the filming of an action scene, a helicopter crashed. The blades decapitated Morrow and Le. Chen was crushed to death. The sequence was removed from the movie, and years of lawsuits followed. And even though nobody was found criminally liable for what happened, the lawsuits revealed that basic safety precautions were not taken. “No movie is worth dying for,” Twilight Zone producer Steven Spielberg said years later. “I think people are standing up much more now, than ever before, to producers and directors who ask too much. If something isn’t safe, it’s the right and responsibility of every actor or crew member to yell, ‘Cut!’”

As Phil Lord and Christopher Miller have proved many times over the 15 years, they can take any concept Hollywood throws at them – no matter how seemingly inane – and turn it into a brilliant film. On paper, films based on Lego characters or the Eighties TV show 21 Jump Street are horrible, bottom-of-the-barrel ideas. In their hands, they were both stellar movies. When word came out that Disney was trusting them with a Star Wars movie focusing on the early days of Han Solo, fans rejoiced. But midway through production, they were fired. “I think these guys are hilarious,” said Lucasfilm president Katheleen Kennedy, “but they come from a background of animation and sketch comedy and when you are making these movies you can do that and there’s plenty of room for improvisation, we do that all the time, but it has to be inside of a highly structured process or you can’t get the work done.” Kennedy hired Ron Howard to take over the project. The end result was not just a deeply disappointing film, but the first Stars Wars movie to underperform at the box office. The fiasco forced Lucasfilm to put their other Star Wars theatrical projects on hold and start focusing on TV shows. We’ll never know what a Miller/Lord Solo would have looked like, but it certainly would have been significantly better than the one we got. When you hire great people, you have to sit back and let them do their thing. Pulling the plug before they can show you a finished product is deeply unfair.

It’s very hard to feel bad for Matt Damon. He’s one of the most successful actors of the past two decades, and he’s swimming in money thanks to the Bourne franchise and other colossally successful movies. But in the 2000s, he had an opportunity to dramatically up his wealth when James Cameron approached him about playing the lead role in Avatar. He was offered 10% of the back end as an enticement. The only problem was that it conflicted with his work on a Bourne movie. “I had to get it all the way to the finish line,” he said, “and I would have to leave the movie kind of early and leave them in the lurch a little bit and I didn’t want to do that.” The decision wound up costing him $250 million. Damon has talked about this several times over the years, but Cameron feels he needs to let it go. “He’s beating himself up over this,” Cameron said in 2023. “And I really think you know, ‘Matt you’re kind of like one of the biggest movie stars in the world, get over it.’” Would you get over $250 million?

Despite all the success that Will Smith had throughout his long career, he always struggled to get taken seriously as an actor. That’s because he started as a rapper, spent years on a sitcom, and was best known for popcorn flicks like Men In Black and Bad Boys. But in 2022, he was finally on pace to receive a Best Actor Academy Award for his role as Richard Williams in King Richard. It was going to be the crowning moment of his career. But shortly before they gave him the award, which everyone knew was coming, Chris Rock made a joke onstage about his wife, Jada Pinkett, who had shaved her head due to alopecia. Smith then walked onstage and slapped Rock hard in the face as tens of millions of people watched. “Keep my wife’s name out your fucking mouth!” Smith roared. It briefly felt like a rehearsed comedy bit, but it was no such thing. Smith still received his Best Actor award that night, and he attempted to apologize, but it wasn’t enough. The Academy banned him from the Oscars for a decade. Apple was forced to delay the release of his new project Emancipation by several months because the slapping incident was such an enormous distraction. The film wound up underperforming anyway. He gave Chris Rock amazing material to use on his next standup tour, but Smith benefited in no way from the incident. It was just a wild, unforced error. 

In 1997, Harvard professor Clayton Christensen published the groundbreaking book The Innovator’s Dilemma. It explained that hugely successful companies often fail in the long run because plucky, disruptive firms with little to lose have an easier time implementing new systems that can revolutionize a business. At the time it was written, Blockbuster was at the peak of its powers. Their video rental stores dotted suburban landscapes and were as ubiquitous as Starbucks or McDonalds. And when Netflix came around and began mailing DVDs straight to consumers, eliminating late fees and the need to leave your house, Blockbuster didn’t see a threat or any need to change their practices. In 2000, Blockbuster was given the opportunity to buy Netflix for $50 million. They turned it down. “Well, shit,” co-founder Marc Randolph recalled saying after the meeting. “Blockbuster doesn’t want us. So it’s obvious what we have to do now … It looks like now we’re going to have to kick their ass.” Flash forward 23 years and Netflix is valued at nearly $200 billion. Blockbuster doesn’t exist for all intents and purposes except for a single store in Bend, Oregon. There were over 9,000 at the chain’s peak. Had they made a different move back in 2000, Blockbuster Netflix could be the biggest name in streaming.

If you were making a big movie in the Seventies or early Eighties and needed a leading man, odds were pretty decent you’d offer the role to Burt Reynolds. The man was a titan of Hollywood throughout the era that pounded out hit movies like Deliverance, The Best Little Whorehouse in Texas, The Longest Yard, Smokey and the Bandit, and Cannonball Run. But he also had a remarkable talent for turning down movies. The streak of colossal bad decisions began when he refused a chance to play James Bond after Sean Connery stepped aside because he felt Americans wouldn’t accept an American Bond. It continued when he said no to the Michael Corleone part in The Godfather, Jack Nicholson’s part in One Flew Over the Cuckoo’s Nest, and peaked when he rejected an overture to play Han Solo in Star Wars. Years later, he even declined an opportunity to play Richard Gere’s part in Pretty Woman. Al Pacino, Roger Moore, Harrison Ford, Jack Nicholson and Richard Gere are forever grateful for these judgment calls, but Reynolds regretted nearly all of them. Hey, at least he agreed to make Cop and a Half, Smokey and the Bandit Part 3, Not Another Not Another Movie.

The 1956 historical epic The Conquerer was awash in bad decisions before they even started shooting the damn thing. The lead role of Mongol conqueror Genghis Khan was originally written for noted non-Asian actor Marlon Brando, which would have been absolutely ridiculous. When he dropped out, they didn’t move onto an actual Asian thespian that could play the role with credibility. They went for John “I believe in white supremacy” Wayne. Did they slather his face with makeup and use rubber bands to pull back his eyes? They sure did. If that wasn’t insane enough, they decided to shoot the movie at nuclear testing sites around Utah. It’s impossible to prove cause and effect, but 41% of the crew developed cancer in the decades that followed, and 21% died from it. That 21% includes John Wayne himself. These people didn’t even die for a good movie. The Conquerer is absolutely horrible. “Wayne portrays the great conqueror as a sort of cross between a square-shootin’ sheriff and a Mongolian idiot,” Time wrote in a scathing review. “The idea is good for a couple of snickers, but after that it never Waynes but it bores.”