Most Cringe-Worthy Pop Culture Moments Ever

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10-05-2025

Certain moments in pop culture just haven't aged well: Think of Friends having Courteney Cox don a fat suit to play 'fat Monica,' or Aaliyah's hit 'Age Ain't Nothing But A Number' ― a song written and produced by R. Kelly, who married Aaliyah when she was just 15.
There were a ton of 'oh, that would never happen today' moments in 2005, which, believe it or not, was 20 years ago. It was a time when Brangelina was all over the tabloids, Tom Cruise was jumping all over Oprah's couch, and MTV was making playful jokes about Diddy's infamous parties, before they led to his downfall.
Below, culture critics and entertainment writers share those and other moments that, in hindsight, really haven't aged that well.
'The 2005 MTV Video Music Awards was hosted by Diddy. Any event with Diddy is already in bad taste now, but to make matters worst, the promotion for the ceremony also featured celebrities like Nicole Ritchie and Derek Jeter providing testimonials over how legendary Diddy's parties were. It could be worse: A few years before, at the 2003 VMAs, Diddy invited a 13-year-old to his afterparty. With recent allegations, it's all incredibly uncomfortable to watch.' ― Kam and Val, the hosts of the 'Empty Theater Club' YouTube channel
Michael Scott's "diversity day" training in The Office
" The Office is a favorite of many and gave us some of the most meme-able moments in television. But despite the fond memories many of us have of the iconic show, there are elements that have not aged well: One of the most egregious from 2005 is the 'Diversity Day' episode. While the premise of Michael delivering a Chris Rock routine in the middle of the office, resulting in HR needing to get involved, remains entertaining, the diversity training that Michael offers is so racially insensitive that it is difficult to watch. That might be the point, but using slurs is still using slurs, and probably (hopefully?) wouldn't fly today." ― Alise Chaffins, a film critic and author of The Ted Lasso Relationship Guide
Tom Cruise's chaotic appearance on Oprah Winfrey's show
'Tom Cruise leaves us speechless every time he does a wild, death-defying stunt in a Mission: Impossible film, but his appearance on The Oprah Winfrey Show left us all thinking, What was that? He was supposed to be discussing his sci-fi movie War of the Worlds, but he simply couldn't contain his excitement that day because he was so in love with Katie Holmes. From punching the ground and laughing incessantly, to clenching Winfrey's hands and doing the iconic couch jump, it's a moment that perplexed us all back when it happened, and it's still so cringey to relive whenever a clip resurfaces. But the most awkward part has to be when he ran backstage to bring Holmes out in front of the audience ― who were chanting 'Katie! Katie!' ― and she looked like she didn't want to be there whatsoever. How she didn't get 'the ick' right then and there is a mystery to us all. (They got married the following year, but divorced in 2012).' ― Ema Sasic, a film critic for Next Best Picture
'Few may remember that the iconic lifestyle guru once had her own spin-off of The Apprentice in 2005. This version saw contestants compete to work for none other than Ms. Stewart herself. The show had lukewarm ratings and was cancelled after one season, which some attribute to the fatigue of airing on back-to-back nights with Trump's version. One has to wonder: if the original plan for Martha Stewart to 'fire' Donald Trump and take over the franchise had gone forward, would we all be living in a better timeline right now?' ― Matt Davis, the creator of Shall I Stream It?
The early-aughts aesthetic and concept of The Girls Next Door
'A reality show originally focusing on three women (Holly Madison, Bridget Marquardt, and Kendra Wilkinson) living at the Playboy Mansion feels right at home on this list. The girls embodied the intense beauty expectations of the early aughts, looking nearly identical with bleached blonde hair and Juicy Couture tracksuits. It's the kind of show that absolutely wouldn't make it to air today, especially since multiple women spoke out against Hugh Hefner in the The Secrets of Playboy documentary. That said, The Girls Next Door is a fascinating documentation of 2005 pop culture, prompting Madison and Marquardt to revisit each episode for a podcast 20 years later.' ― Lexi Lane, a culture writer and director
'This year, we celebrate Marvel's first family, The Fantastic Four, who return to the big screen on July 25. But much has changed in 25 years. In 2025, Sue Storm, played by Vanessa Kirby, is the CEO of The Future Foundation, a fictional organization which works to achieve global peace. But back in 2005, Jessica Alba was left contemplating her future in Hollywood when her version of Sue was written as little more than a romantic foil to her male counterparts. Worse, the filmmakers used her superpower as an excuse for the actress to appear in only her underwear. Luckily, in 2025, our female heroes have graduated from being pretty criers and leather-clad eye candy to fully-realized heroes who save the day side-by-side with their male co-stars.' ― Neil Vagg, the editor of Get Your Comic On
'Say what you will about recent comic-book movies such as Madam Web, J oker: Folie a Deux, and Captain America: Brave New World; one silver lining about the current state of the genre is that we could never reach the lows of portraying superheroines solely as eye candy like we once did in films such as 2005's Fantastic Four. Rather than showing Jessica Alba's Sue Storm grapple with her newfound mutation, the filmmakers go to exaggerated lengths to strip the character naked in order for her to be fully invisible as she's still learning to utilize her powers. Not only would that choice be categorized as creepy and cruel today, as Sue is humiliated in public every time she is discovered to be invisible/naked, but it's a waste of time when you could craft a layered character instead of over-sexualizing them.' ― E dgar Ortega, filmmaker and the co-host of the Where Heartbreak Feels Good podcast
The way race plays out in the King Kong remake
'Peter Jackson's update of King Kong expands the horror classic into a sprawling three-hour film, and the director's predilection for excess contributed to a scene which, in retrospect, hasn't aged great. Granted, it's difficult to separate the knotty racial subtext from the 1933 original, but Jackson's take on introducing the native people of Skull Island doesn't just peddle in a kind of horror savagery born of racial stereotypes; it doubles down. Jack Driscoll (Adrien Brody), Ann Darrow (Naomi Watts) and the rest of their filmmaking crew find themselves surrounded by snarling natives, a horde of monstrous caricatures hissing and gnashing their teeth at the intruders. Rather than the cartoony stereotypes of the pre-Code Kong, these Skull Island inhabitants are explicitly horrific. When they encircle Jack and Ann, the image of Black antagonists closing in on our white heroes doesn't sit well.' ― Brianna Zigler, an entertainment writer and author of Brianna's Digest, a newsletter about lifestyle and pop culture
Hayden Christensen's widely panned performance in Star Wars: Episode III
'2005 was quite the year, with lots of pop culture moments to remember, from Brad Pitt and Angelina Jolie's affair going public, to Kanye West going off script for a Hurricane Katrina telethon that shocked the world and gave us a precursor into who he is. One thing I can't forget? This was also the year Revenge of the Sith came out, and many Star Wars fans agree that Hayden Christensen's acting was not good and hasn't aged well at all.' ― Kristina Oakes, the co-host of the Movie Night Extravaganza podcast
Kirsten Dunst's especially egregious "Manic Pixie Dream Girl"
'In 2005, Cameron Crowe's Elizabethtown gave us the final form of a now-infamous archetype: the Manic Pixie Dream Girl. Kirsten Dunst's Claire may have once felt cute and whimsical, but rewatching it now makes it clear that behind her endless supply of chirpy affirmations, she's utterly hollow. Existing solely to save Orlando Bloom's grieving protagonist (whom she barely knows), this peppy flight attendant spends her time dropping pseudo-profound lines straight out of a Hallmark card, scrapbooking a spontaneous road trip she insists he take, and revealing nothing about herself — not that he asks, either.
MPDGs may have existed before Elizabethtown, but not under an official title. While writing about the film for The A.V. Club, critic Nathan Rabin coined the term, and it's all thanks to Claire. 'I'm impossible to forget, but I'm hard to remember,' she muses at one point. Perhaps her lack of staying power comes from exactly that — there's nothing to remember. Rabin may regret coining the archetype, but in doing so, he and Crowe gave us a lasting reminder of how not to write female characters.' ― Marta Djordjevic, a film history journalist and the author of the Rewind & Revive blog
Those dorky Team Jolie/Team Aniston shirts and hats
'When Brad Pitt and Jennifer Aniston split and he got with Angelina Jolie, everyone was wearing a Kitson hot item: baseball tees for Team Jolie or Team Aniston. Paris and Nicky Hilton both wore competing shirts spotted out in LA. This was a tabloid dominating story, and somehow still pops up. The debate of choosing a side between these women was next level. Selling merch to pick a side is something never seen before. I cannot imagine in 2025 people proudly wearing the shirts selecting sides of two women instead of just being angry at the man who cheated on his spouse.' ― Kenzie Vanunu, the founder of Offscreen Central, a film review site featuring female and non-binary writers
The entire premise of the Ryan Reynolds movie Waiting...
'A majority of 2005's raunchy comedy Waiting... starring Ryan Reynolds, Anna Faris, Justin Long, and John Francis Daley could be considered outdated and problematic when viewed with a 2025 lens. Set over a singular day at the 'family-friendly' restaurant Shenanigans, Waiting... showcases the inappropriate behavior of its staff and their interactions with patrons. The 'comedy' at the heart of the film is fueled by scenarios involving flirting with underage girls, flashing people without consent, and constantly using derogatory, homophobic, racist, and sexist terms. The climax of the film has it all on full display (no pun intended): John Francis Daley's Mitch anguishes in possibly the worst first day of work a person can have and explodes with a burst of insults to his new coworkers before finally quitting. In this scene alone, the main character comments on the intelligence of someone with Down syndrome, describes a character as a pedophile, and proceeds to flash an entire party of coworkers in a final act of defiance. Yikes.' ― Connor Petrey, the editor-in-chief at CINEFIED
'Carlos tampers with Gabrielle's birth control throughout the series! Carlos and Gabrielle Solis had a volatile relationship throughout the show, mostly stemming from how Carlos could never fully 'control' his wife. She expressed multiple times her lack of desire for children, mostly for vanity reasons. Nonetheless, it was her decision. Carlos wasn't having it, so he tampered with her birth control. Naturally, she doesn't react kindly to the news. It's seen as a good thing, though, because it's what he wanted, and they're married, they're supposed to have children. In any case, Carlos' plan sort of backfires: Since she was cheating on him with John, the teenage gardener, the baby was most likely John's, but we never get to find out since she suffers a miscarriage.
That being said, this was not the end of Carlos' tampering with birth control. In a later season, he lies to her about having gotten a vasectomy when she had adamantly told him to get one after the birth of their youngest daughter. When she finds out, she is rightfully upset, but Carlos makes her take pity on him by expressing that he lied because he hoped that they would finally be able to have a son. It always felt that Gabrielle was being punished throughout the series because she was the only one of the women of Wisteria Lane who did not want children. Even when she finally has them, she is painted as a bad mother because she seems not to love her children; she could never win in this series, it seems. It was sort of the same case for Lynnette, who kept having children seemingly against her will, because she wanted to keep working, but was discouraged from doing so because of the kids. This series treated women who dared to dream a life outside of motherhood not too kindly.' ―
'The 78th Academy Awards showcased the very best in film from 2005, but apparently, the Academy of Motion Picture Arts and Sciences thought that Paul Haggis' vision of race in Los Angeles was the best movie of 2005 over the beloved and heavily favored Brokeback Mountain. Crash received decent reviews in 2005, but is now looked at as a laughable film and considered by many to be one of the worst Best Picture winners ever, thanks to its absurd and narrow view of race in America and its thinly written, cartoonish characters. Basically, the Academy decided to award a film they deemed important over an actually important movie in Brokeback Mountain, which broke cultural and cinematic stereotypes in telling its story about the forbidden love between two cowboys.' ― Kevin Wozniak, a film critic and writer for Kevflix and Film Obsessive
CBS
'Let me set the scene for most of you: The show was The Will. A multi-millionaire named Bill Long recruits 10 of his friends and relatives to compete in a series of challenges to inherit his 'prized possession,' a large Kansas ranch. This CBS show was outrageous and quickly pulled off the air because of low ratings. Later in the year, the show finally aired all six episodes on FOX, which saw Long's fourth wife (known as the villain) Penny win the ranch. Over the years, we've seen many bad iterations of reality TV shows, but this one was the icing on the cake. Could you imagine what the modern-day version of The Will would look like? I think it would be messy and filled with legal issues. I definitely would watch, but networks are too smart for that.' ― HuffPost.