Tired of Terrible Bosses? 7 Dark Comedies to Watch if You Loved Horrible Bosses

Have you ever dreamed of quitting your job in a spectacular fashion or maybe, just maybe, plotting a tiny bit of revenge on a boss who makes your work life, well, horrible? If you’ve ever chuckled at the dark humor of “Horrible Bosses” while secretly relating to the characters’ workplace woes, then you’re in for a treat! What if laughing at terrible bosses on screen could actually make your Monday mornings a little brighter? Let’s dive into a world of dark comedies that serve up workplace revenge, hilarious schemes, and characters you’ll love to hate – or maybe just love to watch. Get ready to explore 7 must-watch movies for fans of Movies Like Horrible Bosses!

Why We Love Movies Like Horrible Bosses

“Horrible Bosses” hit the big screen and resonated with so many because, let’s face it, we’ve all had a bad boss story or two. The movie took our secret office fantasies – the ones where we stand up to the unreasonable demands and petty tyrannies – and turned them into laugh-out-loud moments. It’s not just about the revenge plots; it’s about the camaraderie of the underdogs, the wickedly funny situations, and the satisfaction of seeing the tables turned on the truly awful people in charge.

If you’re searching for Dark Comedies Like Horrible Bosses, you’re likely craving that same mix of relatable frustration and comedic release. You want films that understand the daily grind, the office absurdities, and the sweet, dark joy of seeing bad guys get their comeuppance – in the most hilarious way possible, of course.

7 Dark Comedy Movies You’ll Love if You Love Horrible Bosses

Ready for your next dark comedy fix? Here are 7 movies that capture the spirit of Films Similar to Horrible Bosses, each offering its own unique flavor of workplace chaos and comedic revenge.

1. Office Space (1999)

“Office Space” is a cult classic for a reason. Peter Gibbons, a software programmer in a soul-crushing corporate job, decides he’s simply not going to work hard anymore. What follows is a hilarious series of events as Peter’s apathy somehow leads to promotions and admiration, while his friends and colleagues struggle with their own office nightmares, including a particularly annoying stapler. This movie perfectly encapsulates the drudgery of office life and the quiet rebellion many of us dream of. Starring Ron Livingston as Peter, Jennifer Aniston, and Gary Cole, and directed by Mike Judge, “Office Space” was released in 1999 and has a runtime of 1 hour and 29 minutes.

Despite being a box office disappointment initially, “Office Space” has become a beloved comedy. It grossed over $12 million worldwide against a budget of $10 million. On review aggregator sites, the movie holds a 77% rating on Rotten Tomatoes and a score of 68 out of 100 on Metacritic, indicating generally favorable reviews. IMDb users have given it a strong 7.7 out of 10.

Like “Horrible Bosses,” “Office Space” taps into the universal frustration of bad jobs and ridiculous office culture. Both films use dark humor to explore the absurdities of the workplace and the desire to escape or rebel against soul-crushing environments. While “Horrible Bosses” escalates to a murder plot, “Office Space” finds its humor in the everyday annoyances and quiet acts of defiance in corporate life.

You can stream “Office Space” on services like Apple TV, and Amazon Prime Video. Check JustWatch to see all your options.

If you’ve ever felt like just another cog in the corporate machine, “Office Space” is your movie. It’s a funny, relatable, and slightly cynical look at the 9-to-5 world, and it will make you laugh even as you cringe in recognition. It’s a must-watch for anyone who appreciates Best Movies Like Horrible Bosses that find humor in the mundane and maddening aspects of work life.

2. 9 to 5 (1980)

Before “Horrible Bosses,” there was “9 to 5” a classic comedy that paved the way for workplace revenge fantasies on screen. This film stars Jane Fonda, Lily Tomlin, and Dolly Parton as three secretaries who are constantly mistreated by their sexist and tyrannical boss, Franklin Hart Jr. After a series of comedic mishaps, they decide to take matters into their own hands, kidnapping their boss and running the office their way.

“9 to 5” is not only hilarious but also a sharp commentary on workplace inequality and female empowerment. Directed by Colin Higgins, and starring Jane Fonda, Lily Tomlin, Dolly Parton, and Dabney Coleman, “9 to 9” was released in 1980 and has a runtime of 1 hour and 49 minutes.

“9 to 5” was a massive box office success, grossing over $103 million domestically and becoming the second highest-grossing comedy film of 1980. The film was also critically acclaimed, earning an 83% rating on Rotten Tomatoes. IMDb users have rated it 7.1 out of 10, reflecting its enduring popularity.

The common thread between “9 to 5” and “Horrible Bosses” is the theme of fed-up employees taking extreme measures against their awful bosses. Both films use comedy to highlight serious workplace issues, though “9 to 5” focuses more on sexism and corporate power dynamics, while “Horrible Bosses” deals with more generalized abuse of power. If you enjoy Revenge Comedies Like Horrible Bosses, “9 to 5” is a foundational film in the genre.

You can stream “9 to 5” on platforms like Amazon Prime Video, and Apple TV. Check JustWatch for streaming options in your region.

Watch “9 to 5” for a dose of retro comedic brilliance with a strong message. It’s a feel-good movie about standing up to injustice, with iconic performances and a theme song by Dolly Parton that you’ll be singing for days. If you love Movies Like Horrible Bosses for their empowering and funny takes on workplace revenge, “9 to 5” is an absolute must-see.

3. Throw Momma from the Train (1987)

Alfred Hitchcock gets a dark comedy twist in “Throw Momma from the Train.” Danny DeVito directs and stars alongside Billy Crystal in this darkly funny film about two men who jokingly agree to “swap murders.” Larry Donner, a writing professor tormented by his ex-wife, and Owen Lift, a meek man controlled by his overbearing mother, find themselves in a twisted pact that spirals hilariously out of control. This movie takes the idea of getting rid of someone who makes your life miserable to an extreme, comedic level. Directed by Danny DeVito, and starring Danny DeVito, Billy Crystal, and Anne Ramsey, “Throw Momma from the Train” was released in 1987 and has a runtime of 1 hour and 28 minutes.

“Throw Momma from the Train” was a solid box office performer, grossing over $91 million worldwide against a budget of $20 million. Critics generally liked the film, giving it a 73% rating on Rotten Tomatoes. IMDb users have rated it 6.8 out of 10, appreciating its dark humor and quirky premise.

While not strictly about workplace bosses, “Throw Momma from the Train” shares the DNA of Films Similar to Horrible Bosses in its exploration of dark, comedic revenge and the idea of eliminating someone who is the source of your misery. Both movies play with the fantasy of extreme solutions to everyday frustrations, albeit in very different contexts. If you appreciate the dark and twisted humor of Dark Comedies Like Horrible Bosses, “Throw Momma from the Train” offers a similarly satisfying, albeit more morbid, comedic experience.

You can stream “Throw Momma from the Train” on platforms like Apple TV, and Amazon Prime Video. Check JustWatch to find where to stream it.

Give “Throw Momma from the Train” a watch if you enjoy your comedies with a side of darkness and a dash of the macabre. It’s a quirky, funny, and suspenseful film that takes the “what if” of dark thoughts to outrageous and hilarious places. For fans of Best Movies Like Horrible Bosses who enjoy a more twisted comedic premise, this movie is a perfect choice.

4. The War of the Roses (1989)

“The War of the Roses” takes the dark comedy of dysfunctional relationships to a whole new level. Kathleen Turner and Michael Douglas star as Barbara and Oliver Rose, a wealthy couple whose perfect marriage devolves into a bitter and increasingly destructive divorce battle. As their resentment grows, their attempts to sabotage each other escalate into absurd and darkly comedic warfare. This movie is a cautionary tale wrapped in wickedly funny scenarios, showing just how far things can go when anger and resentment take over. Directed by Danny DeVito, and starring Michael Douglas, Kathleen Turner, and Danny DeVito, “The War of the Roses” was released in 1989 and has a runtime of 1 hour and 56 minutes.

“The War of the Roses” was a box office hit, grossing over $160 million worldwide. Critically, the film received mixed reviews but holds a 65% rating on Rotten Tomatoes. IMDb users have given it a 6.8 out of 10, appreciating its dark humor and the performances of Douglas and Turner.

While “The War of the Roses” centers on a marital conflict rather than workplace issues, it resonates with the themes of Revenge Comedies Like Horrible Bosses through its depiction of escalating conflict and darkly comedic revenge. Both films explore how everyday frustrations can spiral into extreme and hilarious situations, driven by characters pushed to their limits. If you enjoy Movies Like Horrible Bosses for their over-the-top scenarios and dark humor, “The War of the Roses” delivers a similarly outrageous and darkly funny experience.

You can find “The War of the Roses” for streaming on platforms like Apple TV, and Amazon Prime Video. Use JustWatch to see where it’s available to stream.

Watch “The War of the Roses” for a darkly comedic and over-the-top look at a marriage gone spectacularly wrong. It’s a funny, albeit unsettling, film with powerhouse performances from Douglas and Turner, and it will make you think twice about letting resentment fester. For those who love Best Movies Like Horrible Bosses for their dark humor and extreme scenarios, “The War of the Roses” is a must-watch.

5. Bad Teacher (2011)

Cameron Diaz stars as Elizabeth Halsey in “Bad Teacher,” a hilariously inappropriate and unapologetically lazy middle school teacher. Elizabeth’s only goals are to find a rich husband and avoid doing any actual teaching. When a handsome, wealthy substitute teacher arrives, Elizabeth competes for his attention against a go-getting, overachieving colleague, leading to outrageous schemes and classroom chaos. “Bad Teacher” is all about subverting expectations and finding humor in the least likely of role models. Directed by Jake Kasdan, and starring Cameron Diaz, Jason Segel, and Justin Timberlake, “Bad Teacher” was released in 2011 and has a runtime of 1 hour and 38 minutes.

“Bad Teacher” was a box office success, grossing over $216 million worldwide against a budget of $20 million. While critics were divided, the film holds a 44% rating on Rotten Tomatoes, it was a commercial hit. IMDb users have rated it 5.6 out of 10, acknowledging its humor even if it’s not a critical darling.

“Bad Teacher” shares the spirit of Dark Comedies Like Horrible Bosses by focusing on flawed, relatable characters behaving badly in a workplace setting. While “Horrible Bosses” deals with terrible superiors, “Bad Teacher” flips the script to focus on a terrible employee. Both films find humor in workplace misbehavior and the comedic consequences of letting your worst impulses take over. If you enjoy Films Similar to Horrible Bosses for their irreverent humor and workplace antics, “Bad Teacher” provides a similarly fun and edgy comedic experience.

You can stream “Bad Teacher” on platforms like Apple TV, and Amazon Prime Video. Check JustWatch to see where to stream it.

Give “Bad Teacher” a try if you’re in the mood for some raunchy, irreverent comedy with a lead character you’ll love to hate (and secretly root for). It’s a funny and outrageous movie that doesn’t take itself too seriously, perfect for a lighthearted and slightly naughty movie night. For fans of Revenge Comedies Like Horrible Bosses who enjoy workplace comedies with a bit of an edge, “Bad Teacher” is a great pick.

6. Seven Psychopaths (2012)

“Seven Psychopaths” takes dark comedy to a wildly eccentric and meta level. Colin Farrell stars as Marty, a screenwriter struggling with writer’s block who gets caught up in the criminal underworld when his best friend, Billy (Sam Rockwell), kidnaps a gangster’s beloved Shih Tzu. What follows is a chaotic and hilarious series of events involving gangsters, psychopaths, and Marty’s increasingly bizarre screenplay ideas coming to life. This movie is a mind-bending, darkly funny ride that’s as clever as it is outrageous. Written and directed by Martin McDonagh, and starring Colin Farrell, Sam Rockwell, and Woody Harrelson, “Seven Psychopaths” was released in 2012 and has a runtime of 1 hour and 50 minutes.

“Seven Psychopaths” was moderately successful at the box office, grossing over $33 million worldwide against a budget of $15 million. Critically, the film was well-received, earning an 82% rating on Rotten Tomatoes and a score of 66 out of 100 on Metacritic, indicating generally favorable reviews. IMDb users have given it a 7.2 out of 10, praising its originality and dark humor.

“Seven Psychopaths” might seem less directly related to Movies Like Horrible Bosses at first glance, but it shares the same darkly comedic tone and embraces of outrageous scenarios. While “Horrible Bosses” is about workplace revenge, “Seven Psychopaths” is about chaotic criminal mishaps, but both films revel in dark humor and unexpected twists. If you appreciate the edgy and unpredictable nature of Best Movies Like Horrible Bosses, “Seven Psychopaths” offers a similarly wild and darkly funny cinematic experience.

You can stream “Seven Psychopaths” on platforms like Apple TV, and Amazon Prime Video. Check JustWatch to see where it’s streaming.

Watch “Seven Psychopaths” if you’re in the mood for a smart, quirky, and very darkly funny movie that will keep you guessing until the end. It’s a unique and original film with fantastic performances and a script that’s both hilarious and thought-provoking. For fans of Dark Comedies Like Horrible Bosses who appreciate films that push the boundaries of dark humor and storytelling, “Seven Psychopaths” is a perfect fit.

7. Game Night (2018)

“Game Night” puts a darkly comedic spin on a couples’ game night that goes horribly, hilariously wrong. Jason Bateman and Rachel McAdams star as Max and Annie, whose regular game night with friends turns into a real-life mystery when Max’s brother Brooks is seemingly kidnapped. As the group tries to solve the “kidnapping,” they stumble deeper into a world of criminals and dangerous situations, all while trying to figure out if it’s still just part of the game.

“Game Night” is a fast-paced, funny, and suspenseful movie that keeps the laughs coming as the stakes get higher and higher. Directed by John Francis Daley and Jonathan Goldstein, and starring Jason Bateman, Rachel McAdams, and Kyle Chandler, “Game Night” was released in 2018 and has a runtime of 1 hour and 40 minutes.

“Game Night” was a box office success, grossing over $117 million worldwide against a budget of $37 million. It was also critically acclaimed, earning an impressive 85% rating on Rotten Tomatoes and a score of 66 out of 100 on Metacritic, indicating generally favorable reviews. IMDb users have given it a 6.9 out of 10, praising its clever writing and comedic performances.

“Game Night” captures the comedic energy of Revenge Comedies Like Horrible Bosses through its blend of dark humor, relatable characters in over-their-heads situations, and escalating comedic chaos. While “Horrible Bosses” focuses on workplace revenge, “Game Night” takes everyday people and throws them into an extraordinary, dangerous, and hilarious scenario. If you enjoy Movies Like Horrible Bosses for their dark humor and ensemble casts, “Game Night” offers a similarly fun, fast-paced, and darkly comedic experience.

You can stream “Game Night” on platforms like Apple TV, and Amazon Prime Video. Use JustWatch to check where you can stream it.

Definitely watch “Game Night” if you’re looking for a smart, funny, and thrilling dark comedy that will keep you entertained from start to finish. It’s a movie that perfectly balances humor and suspense, with a fantastic cast and a clever plot that constantly surprises. For fans of Films Similar to Horrible Bosses who enjoy ensemble comedies with a dark and twisty edge, “Game Night” is a must-see.

Summary Table: Movies Like Horrible Bosses

Movie Title	Year	Main Stars	Runtime	Where to Watch	Why Watch?
Office Space	1999	Ron Livingston, Jennifer Aniston	1h 29m	Apple TV, Amazon Prime Video & JustWatch	Relatable office humor, cult classic status
9 to 5	1980	Jane Fonda, Lily Tomlin, Dolly Parton	1h 49m	Amazon Prime Video, Apple TV & JustWatch	Classic workplace revenge, female empowerment, iconic theme song
Throw Momma from the Train	1987	Danny DeVito, Billy Crystal	1h 28m	Apple TV, Amazon Prime Video & JustWatch	Quirky, dark, and suspenseful, Hitchcockian twist
The War of the Roses	1989	Michael Douglas, Kathleen Turner	1h 56m	Apple TV, Amazon Prime Video & JustWatch	Over-the-top marital warfare, darkly funny, powerhouse performances
Bad Teacher	2011	Cameron Diaz, Jason Segel, Justin Timberlake	1h 38m	Apple TV, Amazon Prime Video & JustWatch	Raunchy, irreverent, workplace misbehavior
Seven Psychopaths	2012	Colin Farrell, Sam Rockwell, Woody Harrelson	1h 50m	Apple TV, Amazon Prime Video & JustWatch	Wildly eccentric, meta, clever, unpredictable
Game Night	2018	Jason Bateman, Rachel McAdams	1h 40m	Apple TV, Amazon Prime Video & JustWatch	Fast-paced, thrilling, ensemble cast, clever plot

FAQ About Movies Like Horrible Bosses

Q: What makes a movie like “Horrible Bosses”?

A: Movies like “Horrible Bosses” typically blend dark humor with relatable workplace frustrations. They often feature ordinary people pushed to their limits by terrible bosses or work situations, leading to comedic revenge plots or outrageous schemes. These films find humor in uncomfortable or even morally questionable scenarios, making light of dark situations in a way that’s both funny and thought-provoking.

Q: Are dark comedies only about revenge?

A: Not necessarily. While revenge is a common theme in dark comedies like “Horrible Bosses,” the genre also explores a range of other themes through a darkly humorous lens. This can include social satire, dysfunctional relationships, absurd situations, and characters behaving badly. The key is the comedic approach to potentially serious or uncomfortable subjects.

Q: Where can I find more dark comedy movies?

A: Many streaming services have categories dedicated to dark comedies. You can also search online movie databases and review sites using keywords like “dark comedy,” “black comedy,” or “satire” to discover more films in this genre. Exploring films similar to the ones listed above is also a great way to find more Best Movies Like Horrible Bosses.

Q: Is “Horrible Bosses 2” worth watching?

A: While “Horrible Bosses 2” does bring back the original cast and dark humor, it generally isn’t considered as strong as the first film. If you’re a big fan of “Horrible Bosses,” it might be worth watching for more of the same characters and comedic style, but set your expectations accordingly. Many fans feel the movies on this list offer a more satisfying dark comedy experience.

Ready for More Dark Laughs?

If you’re a fan of Movies Like Horrible Bosses, these 7 dark comedies are sure to give you your next dose of workplace (and beyond!) humor. From office drones plotting rebellion to couples engaging in all-out war, these films offer a darkly funny escape from the everyday grind. So grab your popcorn, get comfy, and get ready to laugh – maybe a little darkly – at the outrageous situations and flawed characters in these must-watch comedies!