Throughout its illustrious history, Disney has created some of the most cherished films, building a stellar reputation for producing cinematic magic. Classic titles like “Fantasia” and “The Jungle Book” continue to captivate audiences, generations after their initial debuts. Yet, not every Disney endeavor strikes gold at the box office. Over the years, the studio has faced major financial setbacks with certain films that missed the mark both commercially and critically. Beyond these financial disappointments, Disney has occasionally found itself in the spotlight for releasing movies that have contributed to unsavory cultural legacies, inviting embarrassment rather than applause.

Disney’s diverse range of film divisions, from the more mature-focused Touchstone Pictures and Hollywood Pictures to six impactful years with DreamWorks SKG, have collectively contributed a surprising number of these less favorable titles. Out of a myriad of cinematic misadventures, five films, in particular, stand out as notable setbacks Disney would prefer to be forgotten. Some of these films perpetuated harmful racial stereotypes, causing discomfort and controversy even at the time of their release. Others missed the mark artistically to such an extent that even Disney’s powerful branding couldn’t salvage their reputations.

These films might not immediately scream “Disney,” but each is a part of the company’s multifaceted past. They serve as regrettable reminders of the studio’s occasional missteps.

Many consider Steve Martin a comedic icon, celebrated for his numerous successful films, but 2003’s “Bringing Down the House” doesn’t make the cut. Emerging from Disney’s Touchstone Pictures, this film is emblematic of the kind of broad comedies the division was known for in the early 21st century. The plot unfolds with uptight lawyer Peter Sanderson, played by Martin, engaging in online dating. To his surprise, he meets Charlene—portrayed by Queen Latifah—a recently released convict who insists he assist in proving her innocence of a crime she claims she didn’t commit.

Through a series of contrived events, Charlene ends up living with Sanderson, catalyzing a sequence of ridiculous antics revolving around racial stereotypes that hinge heavily on the fact that “she’s Black!” Written by Jason Filardi and directed by Adam Shankman, “Bringing Down the House” leans heavily on uncomfortable portrayals of Black stereotypes and ill-timed racial humor. Despite the talents of Martin, Latifah, and Eugene Levy, moments intended to be comedic, such as Levy’s awkward “you got me straight trippin’, boo,” fall flat, instead highlighting the film’s tone-deaf approach to comedy.

The only thing “Bringing Down the House” proves is that, unless he’s directing 2007’s joyous “Hairspray,” Adam Shankman really is one of the worst mainstream filmmakers working today.

One of those huge flops Disney wants you to forget about, 2010’s “Prince of Persia: The Sands of Time” was an obvious attempt to make the “Pirates of the Caribbean: The Curse of the Black Pearl” magic happen again. Not only did it hail from “Pirates” producer Jerry Bruckheimer, but it was also a retro-adventure film hailing from an unusual source material. “Black Pearl,” though, was based on one of the most famous Disney properties ever, a theme park ride that had enchanted people for decades. “Prince of Persia: The Sands of Time,” meanwhile, stems from a video game series that had started in 1989, more specifically the popular 2003 reboot of the same name. 

Needless to say, this wasn’t the kind of timeless material Disney usually exploited for box office hits. The end result wasn’t just boring, it also engaged in egregious whitewashing by having Jake Gyllenhaal and Gemma Arterton as the leads (the only non-white person in the principal cast was Ben Kingsley as, of course, the nefarious baddie). Just nine years before titles like “Aladdin” at least cast non-white performers for its leads, “Prince of Persia” excluded anyone from the Middle East in its adventure.

These troubling racial politics crop up a lot in Disney’s library. “Prince of Persia,” though, provided an especially high-profile (and costly) example of that phenomenon.

Disney releasing a lucrative movie over the Thanksgiving weekend is nothing new. The Mouse House has been launching new in-house animated films in that holiday frame for decades. In 1987, though, Disney’s Touchstone Pictures division launched they year’s biggest movie domestically with the comedy “Three Men and a Baby.” Combining Tom Selleck, Ted Danson, Steve Guttenberg, and a rowdy newborn was a recipe for box office success. This project marked Leonard Nimoy’s first proper non-Star Trek theatrically-released directorial effort and, after making so much money for Disney, Nimoy was a go-to filmmaker for the company’s adult-skewing divisions, even helming the video portions of the Disney theme park ride “Body Wars.” 

Both Nimoy’s connections to Disney and his feature film directorial career were ground to a halt with 1994’s “Holy Matrimony,” a comedy for Disney’s Hollywood Pictures label with a bizarre and off-putting premise. Betsy “Havana” Iggins (Patricia Arquette) is forced to wed 12-year-old Ezekiel “Zeke” Jacobson (Joseph Gordon-Levitt) to secure a $12 million fortune that Jacobson’s older brother and her former lover, Peter (Tate Donovan), left behind. The central conceit of an adult women marrying a minor (even under coercion) is unspeakably creepy.

To boot, the film’s schmaltzy mainstream comedy sensibilities means “Holy Matrimony” never grapples with this truly horrifying plot point. Juxtaposing a tremendously unnerving premise with this hokey aesthetic makes for a deeply regrettable movie that you won’t see promoted on Disney+ anytime soon.

It goes without saying that the best satire movies of all time are vastly superior to the 1998 Hollywood skewering “An Alan Smithee Film: Burn Hollywood Burn.” The feature, with a title employing a common pseudonym directors used to deploy when they didn’t want credit for a movie, is a total mess scrambling to deliver even mild chuckles. The saga of fictional director Alan Smithee (Eric Idle) stealing his newest, revolting movie is chock full of celebrity cameos. Whoopi Goldberg, Jackie Chan, Sylvester Stallone, Billy Bob Thornton, and even former legendary Paramount Pictures head Robert Evans are among the many famous faces appearing as wacky versions of themselves.

No amount of star power, though, can salvage something this disastrous. “Burn Hollywood Burn” just reheats the same old jokes about Hollywood and filmmaking that have been made countless times before. Released in early 1998 by Disney’s Hollywood Pictures division, “Burn Hollywood Burn” was plagued by behind the scenes drama and absolutely abysmal reviews. 

No studio has a perfect track record, and the worst Disney movies of all time prove that the Mouse House is no exception. Still, it’s one thing to deliver a critically derided film like “Wild Hogs” that still makes moolah. The anemic box office numbers for “Burn Hollywood Burn,” meanwhile, added another layer of problems to this nightmare production. From every angle, this woe begotten enterprise was unspeakably regrettable.

Many bad movies start from noble places. The divisive “Megalopolis,” for instance, may register as awful to many, but at least writer/director Francis Ford Coppola had a conceptually noble intent. The dissonance between those starting points and the final result can be fascinating. Then there are bad movies that are rancid from the word “go,” like “Krippendorf’s Tribe.” This was a cynical attempt to mimic the success of other Touchstone Pictures comedies starring Richard Dreyfuss, like “Down and Out in Beverly Hills” and “What About Bob?” 

Cringeworthy derivativeness is far from the only problem here. Here, Dreyfuss plays Professor James Krippendorf, who, for convoluted reasons, poses himself and his family as a tribe of indigenous New Guinea people that he “discovered.” This means white actors like Dreyfuss and Jenna Elfman dressing up in Blackface, “tribal” garbs, and engaging in stereotypical indigenous behavior that would’ve made the producers of 1933’s “King Kong” recoil. Whereas dark comedies like the works of Bobcat Goldthwait use despicable people as springboards for bleak examinations of societal rot, “Krippendorf’s Tribe” is a surface-level work wanting audiences to cheer on Krippendorf for getting away with his scheme.

The shocking racism and dehumanizing jokes permeating every inch of “Krippendorf’s Tribe” are absolutely outrageous. These gags and caricatures were never okay, let alone in 1998. Disney needs to dump every “Krippendorf’s Tribe” DVD in the same cavern “Song of the South” is confined to.