10 Dark Comedies That Went Too Dark For Their Own Good

Dark comedies aren’t for everyone. More often than not, they tackle real-world subjects with a tongue-in-cheek approach, which can prove alienating for the more sensitive viewers (especially those who have dealt with the severe issue the movie is flippantly discussing). Even classic dark comedies such as Heathers generated controversy at the time of release and continue to do so.

Yet, some dark comedies still check both the critical and commercial boxes, like Grosse Pointe Blank, In Bruges, or The War of the Roses. But other movies did not. Either critics (and, subsequently, general audiences) found themselves turned off by the project, or box office receipts were dismal — or a combination of the two. The following dark comedy films went a little too dark and suffered for it, either critically or financially.

Update January 29, 2024: If you are a fan of dark comedies and curious to know which ones just went too far, then you will be happy to know that this article has been updated by Samuel Cormier with more titles and where each movie is streaming.

10 Death to Smoochy (2002)

A rarely-seen Robin Williams film that nonetheless falls far short of greatness, Danny DeVito’s Death to Smoochy is the penultimate of six films directed by the iconic It’s Always Sunny in Philadelphia star. Throw Momma from the Train, The War of the Roses, and Matilda all reached varying levels of success, but like his 1992 Hoffa, DeVito’s final two films largely failed to find their intended audience. In this film, Randolph Smiler (Williams) is a children’s television entertainer with his character, Rainbow. After the crimes he has committed are finally uncovered, he loses his show and is replaced by Sheldon Mopes (Edward Norton) and his own character, Smoochy, a pink rhino. Smiler’s only goal from here on out is to make Mopes lose his job.

What Made It Fail

Unlike Hoffa, which was a would-be prestige picture that generated more apathy than applause, Death to Smoochy and Duplex came and went from theaters like bolts of lightning. However, while the also-dark Duplex didn’t hit theaters with any word surrounding it — a true surprise for an early aughts film with Ben Stiller and Drew Barrymore leading — Death to Smoochy hit theaters with an outright toxic vibe. And it’s not surprising because, for the most part, the trailer accurately sold how unpleasant the whole movie actually is. The contrast between children entertainers and saturated colors against violent sabotage and jealousy was probably way too stark for most audiences. It’s a baffling misfire but also an interesting one with devoted performances from a star-studded cast including Edward Norton, Catherine Keener, and Robin Williams, and it has become a cult classic in the years since its release. Death to Smoochy is available to rent on Apple TV, Prime, and Vudu.

9 World’s Greatest Dad (2009)

Another Robin Williams film unfortunately makes it onto this list. With the prolific career of the actor, it is bound that some would end up in the bad bin. World’s Greatest Dad follows Lance Clayton (Williams) as he tries to pass off his teenage son’s death by autoerotic asphyxiation as a suicide amidst heavy media scrutiny. He himself is a failed writer and teacher of a poetry class.

What Made It Fail

While the film had the best intentions for this project, it most likely went a bit too dark. There are no redeeming events in this film, if for the bittersweet final scene where Williams dives into a pool like a Christian rebirth to the tune of “Under Pressure” by Queen and David Bowie. It is likely that the heavy themes prevented many viewers from seeing the film, resulting in a box office bomb at a measly $295,750 (first only published on-demand before a limited theater release) against a $10 million budget. Still, the movie received average to good critics, applauding the approach to heavy topics with deadpan dark humor, but somehow criticizing that the writers didn’t go even further with full drama. World’s Greatest Dad is available to stream on Hulu, Peacock, and Vudu.

8 That’s My Boy (2012)

That’s My Boy came out the same weekend as Rock of Ages, and like that film, its marketing hinged on playing to both nostalgia and “something new” simultaneously. In terms of something new, there was “Adam Sandler in an R-rated movie” and “Tom Cruise sings,” respectively. In other words, it is not enough to generate audience interest, especially when neither film really works for more than one scene at a time. In That’s My Boy, Donny Berger (Sandler) is an alcoholic man who rests on the infamy of having been involved with a highly covered statutory rape case. In an effort to make money and avoid prison for tax debts, he sets up a televised, reality-TV-style meeting with his estranged son (Andy Samberg).

What Made It Fail

The reviews for That’s My Boy were rightfully poor, primarily citing its mean-spirited nature, which doesn’t exactly make for a cinematic experience commensurate with a summer comedy vibe. The whole film is dark, from the detestable character of Donny Berger, to the idea of the TV show he comes up with (unfortunately, very believable). Audiences don’t want to go to the cinema to see dirtbags who already exist in the television industry. Given its themes, the film had a huge budget of $70 million yet could only generate $57.7 million worldwide, cementing it as a forgettable flop. That’s My Boy is available to stream on CWTV, USA Network, or to rent on Apple TV, Prime, and Vudu.

7 The Hangover Part III (2013)

Technically, The Hangover Part II was the installment of the trilogy that went too dark, but it was The Hangover Part III that felt the brunt of the impact. Part II took things from Vegas to Bangkok, and just about every plot point in the original film was elevated in intensity, often making it seem like one member of the central trio could actually die. And, as far as summer comedy movies go, that can work against the intended effect. The plot takes place two years after the events of Part II, expanding upon that already unpopular story instead of making up a whole new adventure. Also, this sequel is different from the first two films in that it does not describe a hungover where the characters need to trace back their journey to understand how they got to where they woke up.

Related: The Ridiculous Process of Filming The Hangover

What Made It Fail

Since audiences were already turned off by Part II, there really needed to be something about Part III that convinced prospective viewers it had any reason to exist outside of ticket sales. The trailer (and final product) did not come close to selling that notion, and the trailer’s one quasi-effective joke, where a giraffe is decapitated by an overpass, was certainly not a universally appealing bit of humor. So, while Part III cracked $100 million domestically, it still experienced a sharp decline in interest, primarily because audiences figured they were going to get more of the same bits that made Part II a failure. They weren’t wrong, but at least Part II had personality. The Hangover Part III is available to stream on TNT, TBS, truTV, and DIRECTV.

6 Kick-Ass 2 (2013)

Both Kick-Ass movies go dark, but most fans would argue that only one of them does so effectively. And, solid as it was, Matthew Vaughn’s Kick-Ass wasn’t ever going to build a swiftly expanding fanbase, so whatever sequel was released needed to be of a comparable quality to retain what fans there were. In this sequel, the antiheroes are out of retirement, and ready to cause chaos. Kick-Ass 2 didn’t come close to the first film’s good-but-not-great box office tallies, and the disparity between their critical receptions was even more substantial.

What Made It Fail

When it came to critical reception, Kick-Ass 2 was largely viewed as a copy-paste job of the first installment where much of the impact had been diminished, and any depth had been replaced by more expletives and neighborhood bloodshed. In terms of financial results, the 2010 film netted nearly $100 million worldwide against a budget of $30 million, which was respectable but not astounding, so hopes weren’t that high for the sequel. But, with $60.8 million against a budget comparable to the first film’s (specifically, slightly lower at $28 million), Kick-Ass 2‘s drop was too considerable to warrant a trilogy-capping installment. Yet it now does seem like a new Kick-Ass trilogy is in the works. Kick-Ass 2 is available to rent on Apple TV, Prime, and Vudu.

5 Super (2011)

The 2010s was an interesting time for superhero films, as the Marvel Cinematic Universe was just getting started, and the release of The Dark Knight gave the genre a second life. Revisionist takes on the superhero genre started to emerge, kicking off with Watchmen in 2009 and then following with movies like Kick-Ass in 2010 and Green Hornet in 2011 that looked to parody or subvert the genre. One of the earliest and darkest actually came from now one of the biggest names in superhero movies: James Gunn. Super follows Frank Darbo (Rainn Wilson), a short-order cook who becomes a superhero without having any superhuman ability, calling himself the “Crimson Bolt”. He sets out to rescue his wife, Sarah (Live Tyler), who has left him, from the hands of a drug dealer and teaming up with his sidekick, Libby/Bolte (Elliot Page).

What Made It Fail

Super is clearly the product of Gunn’s Troma Entertainment days, which was about gross-out violence and humor and trying to shock the audience. The film’s imagery of what a real-life superhero is is far more violent than Kick-Ass and with even less optimism. The film’s sexual assault scene is one of the most controversial, as it is supposed to be horrific. Still, at the point in which it arrives in the movie during a lot of overly dark comedic bits, it is not surprising that some viewers took it as making light of the subject even when that was not the filmmaker’s intent. The film was never going to be a mainstream box office hit and it never got a full theatrical release, so its box office was only $593,933 against a $2.5 million budget. Gunn would certainly perfect his vulgar-to-heart ratio in follow-up superhero movies like Guardians of the Galaxy and The Suicide Squad, but Super was a movie that seemed tonally confused. Rent or Purchase on Prime Video and AppleTV.

4 Tusk (2014)

Kevin Smith’s later films, particularly his True North trilogy (Tusk, Yoga Hosers, and the forthcoming Moose Jaws), have proved to be far different from his early View Askewniverse stuff and subject to poor critical marks. Criticism primarily focused on the two films’ wild tonal inconsistencies, with both Tusk and Yoga Hosers oscillating between outlandish, referential, niche humor and body horror tropes. Tusk tells the outlandish story of a retired seaman (Michael Parks) who kidnaps a young podcaster interviewing eccentric people (Justin Long) and surgically transforms him into a walrus, little by little.

What Made It Fail

Tusk undoubtedly walks a thin line in the body horror genre and was most likely too gross for the general audience. It did not have the novelty success of other films, such as The Human Centipede, and couldn’t make a profit on an already slim $3 million budget (specifically, $1.9 million returns worldwide). Even body horror fans complained about the cheap special effect of the walrus skin, although the film’s carefully crafted filmography has been praised. Yet, thanks to a respectable and still-building cult audience for the first entry in the True North trilogy, Tusk 2 is most likely en route. Tusk is available to stream on Cinemax, Kanopy and DIRECTV.

3 The Voices (2014)

In The Voices, Ryan Reynolds stars as the troubled Jerry Hickfang, who believes he’s able to converse with his pet dog and cat. Of course, in reality, their words are all creations of his own murderous mind. And, as could be guessed, Reynolds himself provides the voices of the dog and cat. And as could also be guessed, they’re the humorous highlight of this dark comedy.

What Made It Fail

The reviews for The Voices were solid if not astounding, which could very much be said of the film itself (though Reynolds really gives it his all and is easily watchable). While it may seem strange that a movie starring Ryan Reynolds would flop, The Voices came out after a string of unlucky films for the actor, including Green Lantern (infamously negative critics), R.I.P.D. (box office flop), or The Change-Up (negative reviews). Although the budget was kept very low (despite Reynolds and Kendrick’s presence) at a suspected $11 million, the niche horror comedy still barely cracked $2 million worldwide. However, Reynolds himself keeps this film very high on the list of his favorite projects. The Voices is available to stream on PlutoTV.

2 Bad Santa 2 (2016)

The original Bad Santa was a critical and commercial favorite that gave Billy Bob Thornton his best role in years. Bad Santa 2 received the opposite kind of reaction and ruined what was once an interesting (though crass) character. There’s no character growth in Bad Santa 2; there’s just a man who has continued to fall back in his own way, even dragging the first film’s young boy (not so young now) down with him. This time, Willie plans to rob a charity on Christmas Eve. Classy.

What Made It Fail

Terry Zwigoff’s original 2003 film scored $76.5 million worldwide against a budget of $23 million, yet the 2016 sequel could only attract $17.8 million in domestic interest and just over $6 million overseas on a slightly bumped (but reasonable given the time jump) budget of $26 million. Despite the addition of the always-lovely Christina Hendricks, Bad Santa 2 came out in a year of disappointing sequels like Teenage Mutant Ninja Turtles: Out of the Shadows, The Huntsman: Winter’s War, and Alice Through the Looking Glass. While the original film was dark, this one just felt far more meanspirited compared to the original. Regardless of the relatively small budget, given the financial returns and horrendous reviews from critics and fans alike, there was no point in making Bad Santa 2. Bad Santa 2 is available to stream on Paramount +.

1 Happiness (1998)

Director Todd Solontz is known for his use of dark humor to make light of the vices present in modern society. His second film and first success, Welcome to the Dollhouse, explores the concept of a teenage girl who goes completely unnoticed in her day-to-day life and is ready to achieve recognition through any means possible. But with his 1998 film, he may have gone a bit too far. Happiness follows a series of intertwined suburbian characters who each have their dark secrets– some worse than others. There is a man who makes anonymous phone calls to women just to get off, a woman who killed her landlord after he sexually assaulted her, and a pedophile attracted to his own son.

What Made It Fail

Dealing with grim topics including pedophilia, incest, suicide, murder, fatphobia, and overall perversion, Happiness was first refused a screening at Sundance festival; then, the film struggled with distribution through October Films, who dropped it, as well as an NC-17 rating from the MPAA, later on abandoned to the favor of unrated distribution. The idea of approaching such themes in a comedy was a thing that not everyone could bet on but that only Solontz could bring to fruition. Established actor Dylan Baker, who played the pedophile father, definitely took a gamble for this role. With that said, the film received positive criticism for its satire of modern society and managed a shyly successful box office of $5.7 million against a budget of $2.2 million. Happiness is not available to watch online.