The Worst Movie Bosses Ever

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Most people have experienced a difficult boss at some point in their career. That’s likely why stories about bad bosses are so common in movies and other entertainment – we often see ourselves in the characters who are stressed, overworked, and frustrated by their overbearing supervisors. It’s a way to relate and feel understood.

Whether it’s a stressed-out workplace, a highly competitive company, or a demanding brand, bad bosses seem to enjoy upsetting their employees and using them to climb the ladder. And we can’t help but dislike them for this behavior.

Consider David Harken, brilliantly and disturbingly portrayed by Kevin Spacey in the 2011 comedy Horrible Bosses. The film features three truly awful bosses, including one who sexually harasses employees and another who’s unqualified and got the job through family connections. But Harken stands out as the absolute worst, relentlessly threatening and terrorizing those who work for him – and he even goes so far as to commit murder.

Cruella de Vil, particularly as played by Glenn Close in the 1996 live-action Disney film 101 Dalmatians, is a truly unhinged and terrible boss. Obsessed with fashion and fur, she’s a cruel and abusive leader who constantly tears down her employees. Beyond that, she demands they steal Dalmatian puppies so she can turn them into a fur coat – a shockingly evil act.

While many terrible movie bosses are clearly villains, some are just incredibly annoying. Think of Bill Lumbergh, the draining VP from the 1999 comedy Office Space. You probably won’t meet someone like the truly evil David Harken or Cruella de Vil, but you’ve almost certainly worked with a person or two who reminds you of Lumbergh.

When you have bosses like these, the workday can’t end quickly enough! Here’s a list of 10 of the most awful employers ever shown in movies.

The Worst Bosses in Movies

Miranda Priestly in The Devil Wears Prada (2006)

Miranda Priestly is a complicated character – she has some redeeming qualities, and a fantastic sense of style – but no one would realistically want to work for her, especially as an assistant. As the demanding editor-in-chief of Runway magazine, she prioritizes her career above everything, even relationships with friends and family. She gives her employees unrealistic assignments – like asking Andy to get a copy of an unreleased Harry Potter book on very short notice – and readily uses people, even those loyal to her like Nigel, to maintain her power and status.

David Harken in Horrible Bosses (2011)

The film features several awful bosses, including the manipulative Dr. Julia Harris (Jennifer Aniston) and the lazy Bobby Pellit (Colin Farrell), but Kevin Spacey’s Dave Harken is the worst. As the ruthless president of Comnidyne Industries, Harken intentionally creates a toxic and intensely stressful workplace. He’s controlling, prone to violence, and completely lacks compassion, even forcing an employee to skip a family funeral for a promotion he never intends to grant. And, disturbingly, he’s also a murderer.

Gilbert Huph in The Incredibles (2004)

Gilbert Huph, Bob Parr’s boss at Insuricare, is a truly unpleasant person with a big ego. He doesn’t care about the people he works with or the customers he serves, and he’s only interested in making money. He actually pushes his employees to trick customers so they won’t use their insurance benefits. He’s selfish, condescending, quick to anger, and very loud, often yelling at Bob for just doing his job. In many ways, he’s more damaging to Mr. Incredible than any supervillain, almost completely draining Bob’s spirit.

Katharine Parker in Working Girl (1988)

While Tess definitely oversteps by using her boss Katharine Parker’s identity after Katharine’s skiing accident, Katharine initially tried to steal Tess’s innovative business idea and present it as her own. Katharine initially seems like a modern and encouraging boss, but she quickly reveals herself to be ambitious and willing to take credit for others’ work. Despite being affected by the sexism of the 1980s herself, Katharine acts just like the male executives she criticizes, using her team to get ahead and never acknowledging their contributions.

John Milton in The Devil’s Advocate (1997)

Many people have difficult bosses, but John Milton, played by Al Pacino, takes it to a whole new level. He’s not just a bad manager – he is the devil. In the film, he recruits ambitious lawyer Kevin Lomax (Keanu Reeves) to a prestigious New York City law firm. While initially appearing as a charming mentor, John eventually reveals his true identity and systematically corrupts Kevin, exploiting his ego and leading to the downfall of his life. John manipulates Kevin into defending reprehensible clients, tragically impacts Kevin’s wife, and even schemes to bring about the Antichrist through a disturbing family connection. He’s truly a terrifying and awful boss.

Franklin Hart Jr. in 9 to 5 (1980)

Doralee, Judy, and Violet get a chance to act out a dream many workers share: they kidnap their awful boss and take over the office, improving things while he’s gone. Their boss, Franklin Hart Jr., truly deserves it – he’s sexist, treats women badly, and constantly harasses his female employees. Plus, he’s been stealing money from the company for his own benefit. He’s just a thoroughly unpleasant person.

Cruella de Vil in 101 Dalmatians (1996)

Cruella de Vil isn’t just a difficult boss – she’s truly awful. She constantly insults her employees and even those who work for her, and she’s generally controlling and manipulative. She actively tries to sabotage her best worker, Anita, preventing her from getting married, and then rudely intrudes on Anita and her husband Roger’s home, making snide comments and disapproving of their family. But the worst part? Cruella is obsessed with fur and callously steals Anita and Roger’s Dalmatian puppies, intending to make a coat out of them. This behavior is far beyond anything acceptable, and if it doesn’t frighten you, nothing will.

Bill Lumbergh in Office Space (1999)

Bill Lumbergh might not be a villain, but he’s definitely one of the most realistic bad bosses out there. He’s the kind of manager many people actually deal with: someone who’s quietly frustrating, subtly controlling, and not very competent. Working for him would be awful. He’s condescending, makes unreasonable requests, and creates a really stressful atmosphere. He constantly puts down employees like Milton and forces others, like Peter, to work extra hours. Honestly, a little respect and less frustration would go a long way.

Kylo Ren in Star Wars: The Force Awakens (2015)

It’s easy to focus on the galaxy-wide threat Kylo Ren poses, but he’s also a terrible boss. He routinely threatens, bullies, and verbally abuses his officers and Stormtroopers, flying into violent rages when they disappoint him. He’s even quick to execute those who fail, mirroring the brutal tactics of his grandfather, Darth Vader, who was known for Force-choking his subordinates. It seems abusive behavior runs in the family.

Professor Callahan in Legally Blonde (2001)

Professor Callahan initially seems like a helpful and principled advisor to Elle Woods, a student at Harvard. However, he reveals his true nature when he makes unwanted sexual advances toward her during her internship at his law firm. This demonstrates he’s a manipulative and unethical person who abuses his power, and ultimately, a predatory creep.

The 21 Worst Movies of the 21st Century So Far

21. Basic Instinct 2 (2006)

I’m a huge Sharon Stone fan, and honestly, she’s incredible – she can make even the cheesiest lines sound… well, captivating. But even she couldn’t save Basic Instinct 2. It’s just a disappointing movie overall. She totally dominates the screen, acting circles around David Morrissey, who just doesn’t measure up. I never understood why her character was even interested in him – it felt like she saw him as an easy mark. She just seemed to be toying with him! It’s like watching her have fun, but there’s no real challenge for her. He’s just so bland! It’s like the Dream Team playing against a group of beginners – there’s no suspense. Her character is supposed to be a risk-taker, but facing him? There’s absolutely no tension or danger in it.

20. The Book of Henry (2017)

Colin Trevorrow’s follow-up to Jurassic World, The Book of Henry, was a major disappointment – a strange and confusing film. It’s a bizarre mix of magical realism and disturbing themes, and surprisingly, it attempts to tell a story reminiscent of a Christ parable. The plot involves a powerful being’s death allowing a troubled mother to commit a violent act and adopt her mistreated stepdaughter. On top of that, it’s a serious cautionary tale about indifference, delivered through the unbelievable premise of a deceased child prodigy guiding his mother to become an assassin from the afterlife. It sounds unbelievable, but all of this actually happens in the movie.

19. Space Jam: A New Legacy (2021)

Warner Bros. delivered a surprisingly harsh self-critique in Space Jam: A New Legacy, portraying itself as a corporation obsessed with its properties and driven by cold calculation. The movie itself was a major disappointment – it made the original Space Jam look like a masterpiece. While LeBron James wasn’t a bad actor – he performed about as well as Michael Jordan did in the first film – almost everything else about A New Legacy was simply embarrassing. The film completely missed what made the Looney Tunes characters, especially Bugs Bunny, so beloved, turning him into a complaining and gloomy character. Instead of watching this movie, I recommend revisiting some classic Looney Tunes shorts on HBO Max. You’ll find more laughs in a single short than in the entire two-hour film, and the animation is far superior.

18. Catwoman (2004)

In the movie Catwoman, Halle Berry plays Patience Phillips, who uncovers a dangerous secret about her beauty company’s new product and is killed by her employers. However, she’s resurrected by cats, joining a long line of feline heroines throughout history. Now, with all the classic cat abilities – agility, perfect landings, a knack for stealing jewelry, and a love of leather – she fights (and sometimes creates) crime. The movie, directed by Pitof, who came from a visual effects background, isn’t the ugliest film of the 2000s, but it’s notorious for its incredibly poor editing. In fact, the editing is so bad that the actors wear the same outfits for two days straight, a result of scenes being rearranged without any additional filming.

17. Madame Web (2024)

“Madame Web” feels like an older, less polished Marvel movie, reminiscent of films made before the era of the Marvel Cinematic Universe, where adaptations sometimes seemed hesitant to fully embrace their comic book origins. This awkwardness extends to Dakota Johnson’s performance as Cassie Webb, the character billed as “Madame Web” – but who is never actually called that name in the movie. She also spends almost the entire film without wearing a superhero costume. It’s as if everyone involved is a little embarrassed by the project, which, considering the circumstances, is understandable. The film is often silly, strange, and confusing, making even the less successful “The Amazing Spider-Man” look like a masterpiece. It makes you wonder what Kevin Feige, the mastermind behind the MCU, would think if he watched it – that would be an interesting experience.

16. Planet of the Apes (2001)

Mark Wahlberg plays an astronaut who has a really rough time. He gets pulled into a strange purple cloud in space and ends up on a planet inhabited by… apes! After a long and confusing journey, complete with some awkward fight scenes, he finally makes it back to Earth, only to discover it’s now a planet of apes as well. Director Tim Burton, known for his successes in the 80s and 90s, unfortunately missed the mark with this film.

15. X-Men Origins: Wolverine (2009)

The film’s title is a hint of the mess it is. It tries to be an X-Men movie, a Wolverine story, and an origin story all rolled into one, and fails to do any of them well. Director Gavin Hood should have picked a single focus. The film was destined to be a disappointment, attempting to cram together too many different X-Men and Wolverine storylines. Hugh Jackman’s character, Logan, even complains, “We didn’t sign up for this,” which ironically sums up how many viewers felt about the movie itself. Other lines like “We’ve done enough!” and “Wake me when it’s over” feel like the film acknowledging its own problems.

14. Meet the Spartans (2008)

One of the most disappointing trends in recent movie history was the surge of poorly made spoof films that followed the success of the Scary Movie series. Often written and directed by people who worked on Scary Movie, these comedies relied on a simple, and usually unfunny, formula: recreate scenes from popular movies – particularly 300 in the case of Meet the Spartans, but also drawing from films like Shrek, Spider-Man 3, and Happy Feet – with look-alikes and slapstick humor. Even when they were initially amusing, the jokes were often based on fleeting 2000s pop culture references – like Lindsay Lohan and Paris Hilton – making these films feel incredibly dated today. Seriously, avoid Meet the Spartans at all costs.

13. Marmaduke (2022)

As a movie lover, I can honestly say I’ve never seen an animated film look as bad as Marmaduke, and I really hope I never do. It honestly feels like something made just to move money around, or a quick project thrown together to keep the rights from expiring. And the weirdest part? Despite how awful it looks, they got some genuinely funny people – J.K. Simmons, David Koechner, Pete Davidson – to do voices! I don’t understand how that happened. Did they not see the script? The character designs? Were they bribed with private islands? Seriously, Marmaduke is just… terrible. I wouldn’t even recommend it to the kids who used to make up songs about me picking my nose – and honestly, those songs were more imaginative than anything in this movie.

12. Daddy Day Camp (2007)

It appeared nobody from the original Daddy Day Care wanted to return for the sequel. Eddie Murphy, Jeff Garlin, Steve Zahn, and Regina King were all replaced with Cuba Gooding Jr., Paul Rae, Josh McLerran, and Tamala Jones. The director of the first film, Steve Carr, was also absent.

The first movie focused on Murphy and Garlin learning how to run a daycare center. The sequel moves the action to a summer camp, and with their experience, it should have been an easy success. However, like the first film, everything goes wrong – and the movie suffers as a result.

11. Elektra (2005)

Before the Marvel Cinematic Universe took off, things were pretty rough for Marvel fans. After the initial success of movies like X-Men and Spider-Man, studios started rushing out Marvel adaptations without the same level of quality or attention to detail. The low point was probably the movie Elektra. Jennifer Garner returned as the assassin, but the film portrayed her as strangely meticulous – constantly cleaning to avoid leaving any DNA – yet incredibly careless, befriending neighbors while on a mission, and failing to recognize they were her targets. To make things even stranger, Elektra was brought back to life after her appearance in Daredevil and suddenly gained the power to see the future and even rewind time, essentially becoming immortal. Naturally, she used these god-like abilities to fight ninjas. It’s a fitting use of time travel powers, isn’t it?

10. Norbit (2007)

Eddie Murphy is known for entertaining audiences when he plays several characters in one movie, often with the help of impressive makeup. His 2007 film, Norbit, made nearly $160 million worldwide despite receiving negative reviews, considering it only cost $60 million to make.

However, that doesn’t make it a good movie. In Norbit, Murphy’s talent for transforming himself – and the fantastic makeup work by Rick Baker – are used to tell a frustrating story. Murphy plays a meek man who marries a controlling and abusive woman, and he portrays both roles. His performance as the angry and aggressive Rasputia is technically skilled, but relies on cruel and relentless jokes about her weight. He also plays Mr. Wong, a Chinese man who runs an orphanage and speaks with a stereotypical accent. Ultimately, the film is deeply disheartening.

9. The Emoji Movie (2017)

A good movie about smartphones and emojis could be made, but it would need to be much funnier and more critical than The Emoji Movie. Beyond a simple message about accepting others, the film feels exactly like an advertisement from a tech company that relies on selling phones – it basically says using a cell phone will make you popular and more appealing. It’s not very good.

8. Bulletproof Monk (2003)

I saw this movie over 20 years ago, and I was the only one in the theater. Everyone else was smart to stay away! By the end, I was so bored I kept moving around, trying to find a comfortable seat with a better view, but nothing helped – the movie was just bad. Looking back, Bulletproof Monk might have the worst martial arts scenes ever made by Hollywood. It wasn’t entirely the director’s fault, though; it seemed like Seann William Scott did more of his own stunts than Chow Yun-fat. When the actor best known for playing Stifler is the most dedicated action performer in your film, that’s a major issue.

7. Artemis Fowl (2020)

Let me tell you, revisiting Disney’s Artemis Fowl feels like unearthing a time capsule from the early days of the pandemic – a period, if you recall, roughly 65 years ago! While Disney smartly held back most of its big 2020 films, they curiously dumped this one straight onto Disney+. Looking back, that should have been a warning sign. The movie tries to cram the entire ten-book Artemis Fowl series into just 90 minutes, and the result is a confusing mess. Honestly, it’s almost unwatchable. I’m still baffled by how Josh Gad’s character went from burglar to buddy with Artemis without a single line of explanation! It’s a special kind of awful when a streaming movie makes you feel cheated even though you didn’t pay extra, but Artemis Fowl somehow managed to do it.

6. Son of the Mask (2005)

Few movie sequels are as disappointing as one that doesn’t include its star, and Son of the Mask is a prime example. The original Mask was special because Jim Carrey’s energy and talent were central to the character, allowing him to be wildly expressive and funny. But in this sequel, Jamie Kennedy rarely wears the mask – his dog wears it much more often, strangely enough – and when he does, his performance feels forced and unnatural. They even seem to have dubbed over his voice to make him sound more like Carrey.

Believe it or not, a large portion of the movie focuses on the dog being jealous of the new baby and deliberately using the mask to try and harm him. Thankfully, the baby is born with powers of his own and is unharmed.

Just be warned: nothing can prepare you for the bizarre and unpleasant sight of a CGI baby interacting with Jamie Kennedy in this film. It’s a movie that should have been scrapped entirely, just like the mask is discarded at the end of the original.

5. Alone in the Dark (2005)

Uwe Boll gained notoriety as a director by making a series of video game movies, funded by a German tax loophole that ensured they would make money. Think of the characters from the movie The Producers, but obsessed with video games, and you’ll have a sense of his approach.

One of Boll’s worst films from the 2000s, Alone in the Dark, stars Tara Reid as an archaeologist and Christian Slater as a detective investigating the paranormal. It’s nearly impossible to follow the plot, made even more confusing by an incredibly long, 90-second opening title sequence. Considering Alone in the Dark already ranked as the worst video game movie ever made, the fact that it isn’t at the very bottom of this list speaks volumes.

4. Winnie-the-Pooh: Blood and Honey (2023)

This low-budget horror film is a very loose adaptation of the classic Winnie-the-Pooh stories, which are now in the public domain – meaning anyone can freely use them. Unfortunately, it fails as both a slasher movie and a parody of children’s books. Ironically, it only succeeds in making a strange case against the idea of public domain. It suggests that maybe copyright protection isn’t so bad if it prevents movies this bad from being made. Simply put, Blood and Honey is terrible.

3. Dolittle (2020)

Remember the scene in Tim Burton’s Batman where the doctor’s attempt to fix Jack Napier’s face results in the Joker’s iconic, scarred look? The movie Dolittle feels a lot like that—a disjointed and unpleasant experience. It’s as if mismatched pieces from different versions of the film were clumsily stitched together. What may have begun as a more thoughtful project ended up a chaotic mix of silly jokes about bodily functions, talking animals, poor special effects, and Robert Downey Jr. delivering an over-the-top performance that makes even Johnny Depp’s Captain Jack Sparrow seem reserved.

2. The Master of Disguise (2002)

The idea behind The Master of Disguise was promising. A character who can imitate others seemed perfect for Dana Carvey, known for his impressive impersonations on Saturday Night Live. However, there’s a difference between doing impressions and true disguise. A skilled disguise artist would completely transform into their character and become unrecognizable, while Carvey essentially plays himself. It’s incredibly obvious that it’s Carvey, even when he’s dressed as Al Pacino in Scarface or Robert Shaw in Jaws. Many scenes feel more awkward than funny, like the one where he disguises himself as a turtle-like creature. Thankfully, the movie is only about 70 minutes long, but those 70 minutes are strangely uncomfortable and not very funny.

1. Disaster Movie (2008)

The title Disaster Movie is misleading on both counts. The film spoofs recent blockbusters like 10,000 B.C., Hancock, Jumper, Enchanted, Alvin and the Chipmunks, Beowulf, and The Love Guru, but it barely qualifies as a movie itself. It features few developed characters and a weak plot, held together by a constant stream of awful celebrity impressions – so bad, even the characters in the movie point them out.

Honestly, it’s one of the worst films I’ve ever seen. By the time a man was fighting someone dressed in a poorly-made Kung Fu Panda costume, I wasn’t even angry anymore – I just felt sorry for the actors and, especially, for anyone who actually paid to watch it.

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2026-02-04 18:07