Horrible Bosses movies in order Horrible Bosses Marathon
Page Last Modified:
15 December 2025
Most Recent Release:
Horrible Bosses 2 - 2014
Total Runtime:
206 Minutes
Total Items:
2
Average User Score:
(6.5)Horrible Bosses movies in order
Sometimes you just need a good laugh at how disastrously wrong things can go, and that's where the Horrible Bosses movies shine. These darkly comedic tales of workplace revenge capture everything frustrating about your boss, add a chaotic criminal plan, and set three hilariously mismatched friends on a path filled with bungled heists, blackmail, and hitman spoofs. Whether you're watching them for the first time or planning a rewatch with friends, following the right viewing order will make your marathon even more enjoyable. Grab your popcorn and put your phone away (unless you need to call "Motherfucker Jones"). We'll guide you through the ultimate Horrible Bosses movie night.
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Horrible Bosses Movie 98 min. 2011For Nick, Kurt and Dale, the only thing that would make the daily grind more tolerable would be to grind their intolerable bosses into dust. Quitting is not an option, so, with the benefit of a few-too-many drinks and some dubious advice from a hustling ex-con, the three friends devise a convoluted and seemingly foolproof plan to rid themselves of their respective employers... permanently.USER SCORE 7 -
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Horrible Bosses 2 Movie 108 min. 2014Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.USER SCORE 6
The Horrible Bosses franchise shows that a simple concept: three friends trying to take down their terrible bosses, can be a comedy goldmine. It's got comedy legends like Jason Bateman as Nick, Charlie Day as Dale, and Jason Sudeikis as Kurt. Plus, it's got a good dose of black humor, so it's the perfect mix of dark comedy, crime, buddy vibes, and workplace satire. With directors like Seth Gordon and Sean Anders, and production by New Line Cinema, you're in for a wild ride that always goes the extra mile.
Horrible Bosses (2011)
We kick off the marathon with the film that started it all: Horrible Bosses. Seth Gordon directed this movie, which introduces us to three ordinary guys dealing with extraordinarily terrible employers. Nick is being tormented by the sadistic Dave Harken (Kevin Spacey), Dale is trying to escape his sexually harassing dentist boss Dr. Julia Harris (Jennifer Aniston in a legendary role), and Kurt is dealing with the incompetent and bizarre Bobby Pellitt (Colin Farrell at his best). Their solution? A criminal plan that spirals hilariously out of control. This film is a delightful mix of a hitman comedy spoof, a blackmail plotline, and total chaos among friends. The scene where they hire Motherf***er Jones (Jamie Foxx) as a "consultant" is a total comedy gold mine. And let's be real, we've all been there: sitting in an office and thinking, "What if...?" This is perfect for when you first want to watch it or want to watch it again with friends.
Horrible Bosses 2 (2014)
Nick, Dale, and Kurt are back in Horrible Bosses 2, and this time they are their own bosses... sort of. Sean Anders directs, and things get even crazier and more chaotic. Their attempt to bring a successful product to market ends in a comedic heist gone wrong. Then, Rex and Burt Hanson, played by Chris Pine and Christoph Waltz, show up as the new "bosses." The three friends are tangled up in crime again, but this time it's bigger and the plans are even sillier. What makes this follow-up so enjoyable is that it doesn't just do the same old thing. The film builds on their previous mistakes, shows that they haven't learned anything, and throws them into an even more complicated, dysfunctional trio scenario. The chemistry between the three leads is undeniable, and their timing is on point. You can tell they're totally at ease in their roles, which makes the whole thing even more enjoyable.
The Perfect Order for Your Horrible Bosses Movie Marathon
There are only two films in the franchise, so luckily you don't have to look up a complicated watch order or compare timelines like with Marvel. The order is simple and chronological: Horrible Bosses first, followed by Horrible Bosses 2. But that doesn't mean the experience is superficial—quite the opposite, actually. Watching the films back-to-back lets you see how the characters develop (or don't). You get callbacks, running jokes that truly work when you know both films, and subtle parallels between the two stories. The sequel is full of nods to the original, so if you binge-watch the marathon, you'll get double the reward. Hey, have you ever thought about the return of Motherfucker Jones? Or how their naivete keeps showing up in every "masterplan" they come up with?
Tips for Your Horrible Bosses Marathon Night
Planning a movie night? The Horrible Bosses movie marathon is perfect for an evening with friends, pizza, and a few cold drinks. The total duration is just over three hours, so it's perfect for one long sit without anyone dropping out halfway. Set the mood with some cozy lighting, a bit of background music during the breaks, and maybe even a quiz about who has had the worst boss ever (spoiler: probably still not worse than Dave Harken). If you really want to go all out, you can make themed snacks. For example, you could call it "Tooth Hurty Punch" for Julia's dental practice or "Ransom Nachos" for the chaos in the second installment. And don't forget to vote beforehand on who in your friend group resembles Nick, Dale, or Kurt the most. The outcome is always spot-on.
Why This Franchise Remains Binge-Worthy
The Horrible Bosses franchise knows how to milk a simple premise for maximum chaos. It's not a universe-building epic adventure like Marvel, but that's what makes it so accessible. You don't have to remember anything or delve into lore. You just have to sit back and enjoy how everything goes wrong in the funniest way possible. It's a modern comedy franchise that perfectly taps into the frustrations of the working millennial, while remaining ridiculously over the top. That's what makes these movies so enjoyable. And yes, there are only two movies, but they'll keep you entertained all evening with their chaos and quotables. Plus, they're great for rewatching because you pick up on small details and inside jokes you may have missed before.
Your Ultimate Revenge Plot Comedy Night
So, whether you have a nightmare boss (hopefully not), or just want an evening full of failed plans, bad disguises, and the most delicious office workplace satire ever, this marathon is your go-to. The Horrible Bosses movie marathon is an obvious choice for your next movie night. It's got a simple viewing order and a vibe that'll instantly set the right mood. Make sure your snacks are ready, grab your favorite blanket, and get your binge buddies together. Once that first boss shows up, you know it'll be a wild ride full of incompetence, crime, and plenty of laughs. So, here's the deal: who's gonna be the one to call "Motherfucker Jones"?