10 Movies Boomers Can’t Get Enough Of (But Millennials Find Cringeworthy)

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Written By Lori C.

Lori C. writes about movies, TV shows, and the latest updates from the world of entertainment. She studied Film and Television many years ago at university and uses her knowledge to dissect the newest releases. When not in front of a laptop, she wanders around various European cities with a backpack and a little dog.

The movies Boomers love have a special place in our collective cultural heart. Some silver screen classics (think: The Godfather) are still undeniably cinematic gems worthy of all the praise. Yet when it comes to other movies our parents love, well, let’s just say they haven’t aged well. 

With updated sensibilities and a sharp eye for problematic tropes, Millennials often view these vintage flicks through a different, more 21st-century lens. Here are 10 films adored by Boomers that leave their Millenial children scratching their heads. 

Don’t agree with our list? Fantastic! We hope to spark a conversation that bridges the gap. 

The Graduate (1967)

Dustin Hoffman and Anne Bancroft in The Graduate (1967)
Image credit: Embassy Pictures, United Artists via IMDb

At its peak, critics hailed this Dustin Hoffman-led classic as the ultimate coming-of-age tale. It earned seven Oscar nominations and even snagged a win. But today, The Graduate would be viewed as a problematic story about a young man groomed by an older woman. Oh! And that same protagonist is dating the older lady’s daughter. It doesn’t get much messier than that. 

Grease (1978)

John Travolta and Olivia Newton-John in Grease (1978)
Image credit: Paramount Pictures via IMDb

We can’t deny Grease’s status as a cultural phenomenon. It’s got fabulous music and John Travolta, what’s not to like? The movie also features actors in their late 30s playing teenagers, multiple sexual assault references, and a main plotline about a young woman who changes absolutely everything about herself to appeal to a love interest. And fatphobia. There’s a lot of fatphobia. 

From Russia with Love (1963)

Sean Connery in From Russia with Love (1963)
Image credit: © Metro-Goldwyn-Mayer Studios Inc.

To be fair, none of the James Bond movies are what we’d call examples of “woke Hollywood.” This is, after all, an action series about a spy who travels the world, saves the day, and gets the Bond Girl. Of course, there’s a different Bond Girl in every feature. 

But From Russia with Love, starring Sean Connery does a really good job of objectifying its female cast. Especially the Romani women during the opening scenes. 

Indiana Jones and the Temple of Doom (1984)

Raj Singh in Indiana Jones and the Temple of Doom (1984)
Image credit: © Lucasfilm Ltd. & TM. All Rights Reserved.

We’re not saying the second Indiana Jones movie, directed by Steven Spielberg, isn’t entertaining. There’s a reason the flick was the highest-grossing movie of 1984. However, its overreliance on cultural stereotypes makes it quite an uncomfortable watch for Millenial viewers. 

Manhattan (1979)

Woody Allen and Mariel Hemingway in Manhattan (1979)
Image credit: © 1979 – MGM

This beloved Woody Allen classic is about a divorced middle-aged man finding love again in the Big Apple after his wife leaves him for another woman. There’s but one issue with this otherwise sweet and heartwarming tale – The woman (read: girl) he starts dating is a 17-year-old high school student. 

American Beauty (1999)

Kevin Spacey in American Beauty (1999)
Image credit: DreamWorks Pictures via IMDb

American Beauty is the film that made sure I would never look at another floating plastic bag in the same way again. It’s also a flick about a man so unhappy with his lot in life he gets obsessed with his 16-year-old daughter’s classmate. Sure, he never goes through with the act only because the girl confessed to being a virgin, which opens another can of Madonna-Mistress problematic worms. 

Revenge of the Nerds (1984)

Anthony Edwards in Revenge of the Nerds (1984)
Image credit: 20th Century Studios via IMDb

This raunchy comedy is an iconic tale where the underdogs finally get the upper hand over their more attractive and successful peers. But for those watching it in 2023, there are too many problematic scenes to count. From casual racism to homophobia to full-on sexism, there’s something in Revenge of the Nerds to offend almost anyone. 

Dances with Wolves (1990)

Kevin Costner in Dances with Wolves (1990)
Image credit: Orion Pictures via IMDb

This epic follows a white Civil War soldier who walks away from a previous life to join a Native American tribe. Over the years, many have criticized the film’s use of stereotypes and the dreaded “white savior” portrayal. No doubt the filmmakers meant well but didn’t quite hit the mark with this one. 

Never Been Kissed (1999)

Drew Barrymore and Leelee Sobieski in Never Been Kissed (1999)
Image credit: 20th Century Studios via IMDb

In this 90s comedy, Drew Barrymore stars as a 25-year-old reporter who goes undercover as a high school student. So far, so hilarious. And then there’s that storyline where the protagonist’s love interest is her class professor. While Barrymore’s character is old enough, the teacher doesn’t know that for most of the film but pursues her anyway. 

Shallow Hal (2001)

Shallow Hal (2001)
Image credit: 20th Century Studios via IMDb

It’s almost impossible to defend Shallow Hal. This is the movie featuring Gwyneth Paltrow in a fat suit. Need I say more?

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Pride and Prejudice Focus Features
Image Credit: Focus Features

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Image Credit: Paramount Pictures

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Bohemian Rhapsody 20th Century
Image Credit: 20th Century Fox

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