As much joy as the movies continue to bring, the cinema has also seen more than its fair share of disasters. Many of the worst films ever made, for instance, were seemingly unleashed with little to no regard with just how offensive they would be to unsuspecting moviegoers. In much the same way, some films have unfortunately offered characters infused with so much racism — whether intentional or otherwise — that we can’t help wonder how they managed to make it to theaters.

And while some of the worst offenders featured on this list can be blamed on the prejudices of a bygone era, there are also plenty of recent examples that highlight how far Hollywood still has to go when it comes to avoiding offensive stereotypes and promoting diversity. For this list, any film with a blatantly racist movie character portrayal is fair game, though we’re trying to incorporate a variety of offenders.

1. Jack Robin, The Jazz Singer (1927)

This film may be renowned for being the first real talkie back in cinema’s early days, but sadly, it also features one of the most blatant examples of blackface ever put to film. Star Al Jolson may have been bringing a common stage practice to the big screen with his use of this practice. Yet, it doesn’t change the fact that the film comes across as incredibly racist by today’s standards. Even worse, 1986 “comedy” Soul Man attempted to use blackface for comedic effect, but we give the edge to The Jazz Singer due to its historical relevance.

2. Uncle Remus, Song of the South (1946)

Any number of Disney characters could have taken this slot. The depiction of Native Americans in Peter Pan, the crows in Dumbo, and even a particularly shameful Siamese cat in The Aristocats were all in the running, but while those films are readily available, Disney has effectively disowned this one. James Baskett’s portrayal of the genial Uncle Remus has been the subject of enormous controversy, as has the film’s depiction of race relations after the Civil War.

3. Mr. Yunioshi, Breakfast at Tiffany’s (1961)

By far one of the most egregious entries on this list, Mickey Rooney’s cliche-ridden performance as Holly Golightly’s (Audrey Hepburn) landlord is a terrible example of a white actor embodying an Asian stereotype. While the character’s accent, general demeanor, and role in the story alone would have made him worthy of this list, the casting of Rooney makes it an especially ill-conceived performance.

4. Tony Montana, Scarface (1983)

Sure, everyone loves Brian De Palma’s crime epic chronicling the rise and fall of Cuban druglord Tony Montana (Al Pacino). However, while most fans are busy quoting Pacino’s memorable dialogue and reveling in the film’s unabashed violence, the film does manage to cast a non-Latin actor in a role that is filled to the brim with stereotypes that paint Latin Americans as greedy, drug-addicted criminals. Granted, this is the world in which the film is set, but the fact that no one even stops to consider the appropriateness of Pacino’s performance makes it even more offensive.

5. Long Duk Dong, Sixteen Candles (1984)

John Hughes has brought countless classic films to the big screen, and while Sixteen Candles is beloved by many, there’s no excusing the blatant racism at play in the film’s depiction of this foreign exchange student. From his accent to his bizarre behavior, everything about Long Duk Dong makes us want to shake our heads in disappointment. His appearance onscreen is even marked by a gong. Really?

6. Jar Jar Binks, Star Wars: Episode I — The Phantom Menace (1999)

By far one of the most widely reviled characters ever put to screen, Jar Jar Binks (voiced by Ahmed Best) is also an offensive play on a number of stereotypes relating to African-Americans. His clumsiness, dimwitted good nature, and subservience to the Jedi almost paint him as a slave-type character whose only heroic deeds happen solely by accident. Honorable mention goes to the characters of Nute Gunray and Watto, who are also troublesome.

7. The Wilson sisters, White Chicks (2004)

Just because Shawn and Marlon Wayans disguise themselves as the titular Caucasian women in this comedy doesn’t excuse the fact that the film’s jokes are almost entirely based on stereotypes exclusive to white people. Yes, racism works both ways, and White Chicks essentially coasts on what it perceives to be the humor derived from the distinction between two different races. Moreover, their creepy disguises just plain weird us out.

8. Zohan, You Don’t Mess with the Zohan (2008)

Adam Sandler films routinely incorporate stereotypes of all kinds to supplant the lack of actual comedy, but this one — which features Sandler as an Israeli soldier who fakes his death to become a hairdresser — may take the cake. It also features equally objectionable performances by co-stars like Rob Schneider and John Turturro that manage to stretch the thin comedic setup of the film to its very limits.

9. Guru Pitka, The Love Guru (2008)

After the Austin Powers and Shrek films hit it big, Mike Myers could seemingly do no wrong (well, except for The Cat in the Hat, but we digress). Then this mess happened. Myers’s character is a blatant play on Indian stereotypes, and his performance — coupled with the film’s depiction of Hinduism — sank its hopes of becoming a box office hit. In fact, The Love Guru remains Myers’s last live-action lead film role to date.

10. Mudflap and Skids, Transformers: Revenge of the Fallen (2009)

No one ever accused Michael Bay of being particularly sensitive, but even so, these two characters — voiced by Reno Wilson and Tom Kenny, respectively — take the offensiveness to a whole new level. Jive-talking robots who bear gold teeth and lack the ability to read? That’s a pretty blatant case of racism any way you slice it. Luckily, Mudflap and Skids have yet to reappear onscreen.

Follow Robert Yaniz Jr. on Twitter @CrookedTable

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