One of the most bizarre gross-out comedies ever produced, Nothing But Trouble is the demented brainchild of writer/director/star Dan Aykroyd, who was inspired by his own surreal experience with a traffic court in upstate New York. Hoping to craft something more in line with Beetlejuice, Nothing But Trouble follows a financial publisher (Chevy Chase) who becomes smitten with a young lawyer (Demi Moore), who get lost while escorting around their clients (Taylor Negron and Bertila Damas) and wind up in the remote, impoverished New Jersey town of Valkenvania. After getting pulled over for traffic violations, the four are forced to stand trial before a vile and sadistic 106-year-old judge (Aykroyd), who rules his run-down town with a penchant for capital punishment. A rare misstep for all involved, Cowboys & Aliens was initially intended to be the next high-concept studio tentpole film in the vein of Men in Black or Transformers after more than a decade of development under the DreamWorks Pictures umbrella. Employing an all-star cast, as well as the most in-demand writers and producers of the time, Cowboys & Aliens revolves around an outlaw (Daniel Craig) who awakens in the desert without his memories but with a strange bracelet that could possibly be the key to saving a local town from an extraterrestrial threat. However, the film’s mismatched tone and audience-repelling title left the movie dead on arrival, as Cowboys & Aliens only grossed less than $12 million more than its reported production budget. Does anyone else remember the collective groan of audiences in any given movie theater where the Battleship trailer would play? A colossal miscalculation on every fathomable level, Battleship was truly a shining example of “who asked for this?” from an underwhelming and uninspired cast to a concept that didn’t even feel organic to the game itself. In fact, it is still somewhat surreal to imagine the meetings that had to go into developing the Battleship board game into a big-budget cinematic fiasco, especially one lacking in tangible star power and doubling down on a shoehorned sci-fi premise that hasn’t even helped the film find a following as a syndicated late-night cable staple. One of those “Good Lord, how did THIS get made?” comedies from the early ’00s, all the good intentions in the world can’t stop Shallow Hal from feeling like true cringe 20 years later. The movie follows Hal (Jack Black, in one of his first leading roles), a superficial womanizer who is hypnotized by Tony Robbins to only see people’s inner beauty, leading him to fall madly in love with an overweight woman. It’s an offensive and embarrassing outing that feels icky by any standards, and the fact that it made more than $140 million at the box office back in 2001 is all the more shameful. There’s an almost endearing quality to Blumhouse’s attraction to reviving ancient IP for their potential franchises, but few films were as self-indulgent and conceptually mismanaged as their horror reboot of Fantasy Island from 2020. From the toothless PG-13 horror to the undercooked and bizarre comeuppance scenarios to the mental gymnastics in play to justify and introduce the more notable elements of the original 1977 television series, Blumhouse’s Fantasy Island seems to be lost at sea while desperately swimming to an out-of-reach island of relevancy. Toss in the fact that the film came out less than a month before the COVID-19 pandemic hit the US and hosts a Cinemascore of “C-” among polled audiences, it seems that nobody is particularly excited to return to Fantasy Island. Not to be confused with the feature film conclusion to the space Western series, Firefly, this star-studded cinematic enigma starts off as a modern noir, albeit with a much sillier setting, over-the-top performances from the whole cast, and a number of truly mind-numbing creative choices. But once the film begins to drift into science fiction territory and commits to becoming full-on camp, Serenity becomes a film nobody anticipated and, honestly, one of which you can’t quite make heads or tails. While there’s a good chance that Serenity might become a midnight movie, ala The Room or Fateful Findings, this box office bomb is more likely to be forgotten by audiences even despite its absolutely bonkers third act. At the time, Johnny Depp and Gore Verbinski had teamed up for one of the highest-grossing franchises in Disney’s history with Pirates of the Caribbean while Armie Hammer was earmarked as the next Hollywood star following his breakout performances in The Social Network and J. Edgar. However, none of these elements could help save this bloated western, as modern audiences were not exactly keen on seeing this long-winded revival of the golden-era cowboy hero. A massive loss for Disney, The Lone Ranger’s failure at the box office might have been a happy accident, considering the controversies surrounding both Depp and Hammer in recent years. By the late ‘00s, Mike Myers was one of the most dependable comedians working in the feature film space, having no less than three incredibly profitable franchises to his name with Austin Powers, Shrek, and Wayne’s World. But when the Canadian comedy hitmaker broke out an ill-advised accent, a surreal beard, and an unusually self-indulgent concept set in the world of hockey, it turned out to be cinematic kryptonite, repelling audiences and critics alike. The film remains a black mark on Myers’ resume and essentially sent the comedian away from the limelight for nearly 15 years until he introduced his brand of comedy to a new generation in Netflix’s The Pentaverate. After becoming a filmmaker to watch due to the underground success of his directorial debut, Donnie Darko, Richard Kelly kept that same sense of ambition and bravado for his follow-up film, Southland Tales. Yet even with the help of a wildly talented ensemble cast, including Dwayne “The Rock” Johnson in an early lead role, Southland Tales wound up playing like an incoherent tonal rollercoaster, complete with Justin Timberlake lip-syncing The Killers, a bevy of surreal cameos and a faux car commercial that includes two vehicles having sex. Richard Kelly would eventually get a chance to redeem himself with subsequent opportunities in the director’s chair, but Southland Tales remains a cinematic cautionary tale for young filmmakers. The ’80s had a lot of ridiculous elements that now get viewed with rose-colored glasses as endearing cultural touchstones, from bold hairstyles to flamboyant fashion choices. However, there were plenty of times when these weird and wild aspects of the decade go overboard, and Voyage of the Rock Aliens is a perfect encapsulation of them all. Developed as a star vehicle for singer-actor Pia Zadora and featuring the likes of Craig Sheffer (One Tree Hill), Ruth Gordon (Rosemary’s Baby), and Jermaine Jackson (of the Jackson Five), Voyage of the Rock Aliens tries to be equal parts Grease and Star Wars, which turns out to be a combination as disastrous as you think it might be. Listen, I know that the novel Abraham Lincoln: Vampire Hunter was a critical and commercial success, as author Seth Grahame-Smith’s combination of absurdity, horror lore, and biographical detail made for a unique reading experience in the vein of his breakout book, Pride and Prejudice and Zombies. But while the comedic concept works well enough on the page, the humorless big-screen adaptation from the director of Wanted baffled audiences by doubling down on visual style, including the then-popular 3D release, over investing in the surreal atmosphere that naturally surrounds such a project. As a result, most people were left cold by the straight-faced take, proving that sometimes it’s better for the audience to laugh with your movie than not laugh at all. I wouldn’t necessarily be surprised if you hadn’t known that Donnie Darko received a direct-to-video sequel, as the film had very little marketing and the only connective tissue between the films is Daveigh Chase, reprising her role as Donnie’s younger sister more than eight years after the first film’s release. Nevertheless, the sequel that no one asked for was a bust with fans of the series, critics who saw right past the film’s intentions as a cheap knock-off of the original’s defining attitude, and even Richard Kelly himself, who went out of his way to distance himself from this ill-advised blunder. I don’t know what cruel and unusual domino effect needed to happen to get pop culture from Scary Movie and Not Another Teen Movie, which all have their merits and genuinely funny moments, to the lifeless dreck that is Epic Movie, a spoof movie taking inspiration from the trailers of Hollywood’s biggest films while throwing in random celebrity cameos in an attempt for a cheap laugh that never comes. Fun Fact: when I went to see Epic Movie in the theater, a member of the audience stood up and yelled “What is this?! This isn’t a movie!” Looking back, he couldn’t have been more right, and hopefully, the beast that spoofed movies will remain dormant for a while, or at least until someone with an actual funny bone in their body can whip up some worthwhile parody ideas. Oh just because the other creative minds behind parody movies in the ’00s doesn’t mean that the Wayans Bros., who initially delivered some drop-dead funny flicks like Don’t Be A Menace… and I’m Gonna Git You Sucka in the ’90s, are off the hook for some of the cinematic crimes to their name. While most gravitate toward the nightmare fuel that is White Chicks, there’s something even more problematic and off-putting about Little Man, a film that uses face-swapping technology to portray Marlon Wayans as a little person who decides to pass as a baby in order to steal a stolen diamond stashed in the handbag of a woman who desperately wanted a child. Though the film was a minor success at the time, Little Man has aged like milk on a summer day in the years since. Outside of the Fast & Furious saga, Guardians of the Galaxy, and, to a lesser extent, the xXx and Riddick franchises, Vin Diesel has had a bit of a hard time finding the next big property to his namesake in Hollywood. Some didn’t work out so well, such as Babylon A.D., while others were the victim of circumstance, such as Bloodshot, which hit theaters only days before the COVID-19 pandemic took hold of the world. But no Vin Diesel vehicle baffled audiences and critics quite like The Last Witch Hunter, a film that indulged Diesel’s D&D fandom and sensibilities while feeling more at home with the bizarre contemporary fantasy films of the 1990s. Nevertheless, no one was particularly enthusiastic about exploring the world of The Last Witch Hunter, as the film has fallen into obscurity over the past seven years. Produced by the Farrelly Brothers, who make their second appearance on this list, The Ringer is not just a film that is confusing in its own existence but one that borderlines on ugly at times. I understand that the film carries the endorsement of both The Special Olympics and Best Buddies, programs that both empower and mentor those with disabilities, while also employing various individuals with intellectual disabilities, and does indeed plant its feet in a message of treating everyone with respect and dignity, which is ultimately what the film should be about. But the story of which these themes are a conduit, as well as some of the non-disabled performers in prominent supporting roles as characters with disabilities, feels inappropriate and regrettable at the very least. Few modern movie decisions left their audience scratching their heads as hard as The Dark Tower movie, having been developed over so many years to eventually become something that feels incongruent to the entire mythos of the novels. But even beyond alienating the film’s built-in audience, the film somehow even found a way to make Stephen King’s voice feel tired and rote, eventually composing an emotionally impenetrable film about good versus evil where you don’t even care who wins. While King fanatics still hold out hope that a proper Dark Tower adaptation might come one day, this one ain’t it, fam. Perhaps best known to contemporary audiences as the movie from which Paul Rudd would play a particularly peculiar clip every time he appeared on Conan, Mac and Me is a cult relic of a time when Hollywood would more than happily craft propaganda on behalf of McDonald’s in the form of a goofy E.T. ripoff. However, the film would veer closer to kinder trauma than children’s classic, and with Mac and Me’s many product placement scenes and even a sequence featuring Ronald McDonald himself dancing with children, critics and audiences universally decided that the film works better as a pop culture punchline than a feature film for the whole family. Developed and released less than a year before World Championship Wrestling would go out of business, Ready to Rumble is a cinematic car crash that somehow botches both the world of professional wrestling and comedy filmmaking in one swoop. Granted, it’s at no fault of the performers, as David Arquette is trying his best and the likes of Joe Pantoliano, Oliver Platt, and Martin Landau at least appear to be having fun, but the film itself feels like a time capsule from 1999 was thrown into an AI screenwriting machine, as gross-out humor, pro wrestling antics, and hyper-stylized music video camerawork all feel embarrassingly dated.
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