Some of the Best Cringe-Worthy Movies of the 1990s (Pt.1)

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The 1990s were a unique time for box office movies; we had romantic comedies that, while delightful in their way, would never hold up to today’s cultural standards. Epic action films that could lean into the just far-out enough global climate catastrophe scenarios that are a little too close to home nowadays. Horror films and thrillers rested on age-old gender stereotypes. It was a light-hearted time, and while we all have our favorite movies, there are some in particular that if you are going to re-watch, just fair warning, you might need to laugh off the cringe to be able to enjoy it.

My Best Friend’s Wedding – The Most Toxic RomCom (1997)

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In ‘My Best Friend’s Wedding,’ the main character, Jules (played by Julia Roberts), is a neurotic food critic with a flirty relationship with her best friend, Michael, who is about to get married at the last minute. Jules, intent on getting Michael’ back,’ goes on an ethically dubious rampage to get him to break up with his fiance. Micheal is a bit skeezy and has convinced his younger girlfriend Kim to drop out of school and travel with him for his sports writing gig. 

The fiance, Kim (played by Cameron Diaz ), asks Jules to be her maid of honor because apparently she has no friends (?) George, Jules’s gay friend, drops everything to help his straight friend’s romantic scheming, such as Jules using Kim’s father’s email account(!) to forge a message from him to Michael’s boss, asking that Michael be fired. Jules and their gay friend Michael then pretend to be fiancees to make Michael jealous. The movie ends with Miachal and Kim getting married anyway, and Jules makes an excellent wedding reception speech. Uff. 

Armageddon – A Movie We Somehow All Loved (1998)

Armageddon (1998) was a blockbuster film that definitely does not hold up to today. The plot goes like this: a giant asteroid is coming to destroy the Earth, but somehow, only the United States knows about it, and the U.S. president will make the announcement. Somehow, China, Russia, or any superpower has no clue. The big plan of NASA is to send a blue-collar oil driller (Bruce Willis) and his goofball friends up to space to destroy it. There are three women in the movie who, of course, do not interact at all (would not pass the Bechdel test). Grace (played by Liv Tyler), the daughter of Harry, the oil-digger and paramour to his young coworker A.J – whose only purpose in life is to connect these two macho men, her solo screen time is just her moping in a space station room by herself. Harry decides to sacrifice himself to save the world but states that A.J. (played by Ben Affleck) must marry his daughter, as his dying wish, talk about pressure. 

The Indian in the Cupboard – Not So Competent Native American Recognition (1995)

There’s a young boy named Omiri, who, for some reason, gets a cupboard gift for his birthday. His friend gifts him a small figurine styled like a Native American, stating, “It reminded me of you” (no explanation needed). Omri puts the figure in the cupboard, and the figurine comes to life when he opens it. ‘Little Bear,’ who comes alive, is whipped away from his ‘real life’ with an Iriqouis tribe. And then Omri brings more figurines alive who, unfortunately, not all live through the shock of coming to life. Omri begins to learn more about “Little Bear,’ and when a punk kid with a mohawk steals his change on the street, he yells, “You don’t deserve that hair!” – very progressive calling out cultural appropriation. Then “Little Bear” goes home for good, but not before asking about the fate of his people, to which point Omri closes the cupboard door. 

Never Been Kissed – Predator Alert (1999)

Josie Geller (played by Drew Barrymore), a copyeditor at the Chicago Sun-Times, tells her coworkers that she has never been kissed. Her boss decides he doesn’t know anything about high school kids these days and sends Josie on her first story as a reporter to go on a massive undercover operation to pretend to be a high school student. Josie’s fashion and looks don’t raise any flags about her age difference. She then falls head over heels for a young high school boy. The newspaper decides to put a hidden camera and mic on Josie so they can all watch her and the skirts of high school girls from monitors. Then, somehow, Josie’s creepy, full-grown brother enrolls in high school to help her become popular through made-up rumors on her behalf.

20th Century Fox

Meanwhile, Josie is now falling for her teacher, and maybe we’re supposed to think it’s okay because she is 35. However, the teacher definitely still thinks she’s a young student. Josie’s older brother is now dating a high schooler. Josie becomes Prom Queen while her love-stricken teacher looks on in jealousy. When Josie finally breaks the news that she is, in fact, an older adult woman, her love interest is somehow no longer interested. But alas, Josie finally gets her big first kiss from the teacher; I guess all’s well that ends well.