“Should’ve Been Enough To Put Him Behind Bars”: 41 Pop Culture Moments And Trends That Aged Poorly

Jason Sargent Tuesday, April 28, 2026

Rokas LaurinavičiusTue, April 28, 2026 at 6:35 AM UTC

The entertainment industry sells more than concerts and movies. It also promotes a way of life, shaping what’s considered cool and trendy. However, what music producers and Hollywood PR managers push isn’t necessarily what should be normalized in the first place.

Last month, a new subreddit was created. It’s called ‘Why Were We Ok With This?’, and the online community already has 374K members.

According to the group’s ‘About’ section, they post pictures that allow you to look back at shocking things from previous decades that we were okay with for some reason — including exploitative TV shows, tabloids, paparazzi, and random cultural moments that just make you gasp in hindsight.

From crazy diets to (casual) sexism and even potential criminal cases, think of the content as a mix of laughing at the ignorance of the past and critiquing it seriously.

#1 Khloe Kardashian Walked 4 Black Women On Leashes

At a Halloween party in 2003, Khloe Kardashian, dressed as a pimp, walked four Black women on leashes. There was no controversy over this at the time and there has only been backlash since it resurfaced in 2022.The four women are sisters Meagan and La'Myia Good and sisters Malika and Khadijah Haqq.When it started getting attention, Meagan said, “That one time on Halloween when you were young and dumb …and clearly didn't think 15 years ahead lol smh. Welp, mistakes were made.”Khloe Kardashian has not commented.

#2 Billy Wyman (48) With His Girlfriend (14) He Married Her When She Was 18

#3 25 Year Old Ashton Kutcher, Talking About 15 Year Old Hilary Duff

#4 Paul Walker Was 33 When He Dated His 16 Year Old Girlfriend

#5 The Entirety Of Conor Kennedy And Taylor's Swift's Relationship

Now that Taylor Swift has found a fiancé and the Kennedies are relevant again, let's talk about when a woman born from 1989 dates a child from 1994 in 2012. She was signing him out of school for dates, dressing early 60s, taking photos at the graveside (all this was just after his mother passed away, mind you.) She brought the house next door and showed up to a wedding uninvited.

#6 Grooming: Wilmer Valderrama History Of Grooming Teenagers

He was 20 when he dated Mandy Moore and she was 16.He was 24 when he dated Lindsay Lohan and she was 17.He was 29 when he dated Demi Lovato and she was 17.I think That 70s show is cursed.

#7 The One(S) With All The Fat Jokes

#8 Rolling Stone’s Infamous August 2004 Magazine Cover Calling Lindsay Lohan “Hot, Ready, And Legal” When She Turned 18

#9 Sexism On Toddler Clothes

#10 Bridalplasty- The Plastic Surgery Competition Show

Bridalplasty was a show that followed 12 engaged or already married women competing for the wedding of their dreams and their dream plastic surgery procedure. Each woman had a plastic surgery wishlist, and the winner of each week's wedding-themed challenge would win one plastic surgery procedure from her list.The winner of the competition received the wedding of her dreams, and had her entire wishlist fulfilled. The husband-to-be did not see his fiancée until she revealed her new look on their wedding day. Shanna Moakler hosted, and Dr. Terry Dubrow performed the plastic surgery procedures.Challenges including distinguishing between Dom Pérignon and Andre Strawberry Sparkling Wine; winners were rewarded with rhinoplasties, breast augmentations, jowl lifts, and thigh tucks. Bridalplasty’s opening credits show Dubrow hammering a silver pick into a woman’s nose cartilage, pummelling thigh fat with syringes, and forcing silicon implants into torn flesh. This show massively contributed to exploiting people with body image issues and reinforcing beauty stereotypes.The winner ended up receiving a brow-lift, liposuction of the chin, jowls, cheeks, a breast reduction, breast lift, tummy tuck, laser skin resurfacing and liposuction of the inner thighs, outer thighs and arms.

#11 Race-Swapping Reality Show From 2006

Black. White was a reality TV show from 2006, produced by none other than ICE CUBE! In which two families of 3 went under makeovers to pass as each other’s races.It won an Emmy for Outstanding Makeup for a Series!

#12 This Picture Of Russell Brand And Katy Perry With Justin Bieber Is Uncomfortable To Look At

#13 In 2004 Justin Timberlake Ripped Apart Janet Jacksons Costume And A Wardrobe Malfunction Caused Her To Be Exposed

After, she was uninvited to the grammys, suffered major public backlash, had her songs cut by MTV, suffered record sales for her new album and was blackballed from the industry.

#14 Remember When Russell Brand Did This?

Can you imagine living with that maniac? Taking a picture of his then wife Katy Perry at like 4 in the morning then posting it on the internet

#15 Joel Madden Dated Hilary Duff When He Was 25 And She Was 16

#16 R. Kelly, Aged 27, Married Aaliyah When She Was 15

To state the obvious, we know now that Kelly’s relationship with Aaliyah was the tip of the iceberg, but this is one of the best examples of his disgusting behaviour being brushed off at the time.Aaliyah, who sadly passed away at only 22, in a plane crash, started working with Kelly when she was 13 or 14 — he was her musical mentor. It’s alleged that the grooming began at this age. They were illegally married when she was 15 and Kelly was 27, and her age was forged as 18 on the certificate.When the marriage certificate was leaked to the press, after ongoing rumours for some time, some people had ish to say — BUT, people looked riiiight past this so that they could continue enjoying Kelly and Aaliyah’s music. Some people even blamed Aaliyah, shaming her like she wasn’t a child, like the grown man wasn’t to fault.Aaliyah even released an album, under Kelly’s mentorship (i.e. control), at age 15 called ‘Age Ain’t Nothing But A Number’. Kelly wrote the titular track and you can see him looking creepy as hell in the background of the album cover. I wish she’d never had to put her beautiful name to this exploitative album.The marriage was annulled, and records expunged, in 1997 and professional ties were cut. Aaliyah continued to be asked about Kelly in interviews and could not and would not discuss him at all. She also could not discuss him in her personal life. People who were close to her believe this was trauma related — and I don’t see how it couldn’t be.It sickens me that R. Kelly was able to get away with awful, awful things for so long. This alone should’ve been enough to finish him and put him behind bars.May Aaliyah Dana Haughton rest in peace

#17 Gwen Stefani An Her Harajuku Girls

During her L.A.M.B era she used Asian woman as silent props. As soon as the album cycle was over she ditched the whole look an the girls in general, I just find it insanely odd they never once spoke.

#18 Big Rhonda From That 70s Show Being Treated Like She Was 500lbs

I believe Friends did this too (although I never really watched the show). I'm 22 and I remember even as a kid back in 2008 or so watching this and thinking she wasn't *that* fat? A little chubby, sure, but they acted like she was 500lbs, her whole personality was "fat" lmfaoedit: I have to agree with the people stating she's not even chubby, I just didn't know how to describe it as "slightly larger than the other girls on the show"... size medium? Average sized?

#19 The Public Shaming Of A Young Woman Who Was Love-Bombed And Taken Advantage Of, And Ultimately Thrown Under The Bus, By The Most Powerful Man On Earth

Monica Lewinsky made a youthful mistake. She had a fling with the most powerful man on the planet. She was young, and a charming, powerful man love-bombed her and made her feel important. They had a brief affair.The affair would go on to define her in the public eye. *She* was the villain, *she* was the maniac. Late night talk shows, daytime newsbyte shows, radio hosts, EVERYONE was piling on her.While Bill Clinton did face an impeachment hearing, the public mostly gave him a pass, while crucifying this young woman.She spent the following decades with this cloud hanging over her. She couldn't get jobs. She was a constant punchline. She considered changing her name briefly at the suggestion of others, to have some semblance of a normal life, until she put her foot down, and said "Nobody suggested Bill Clinton should change *his* name.Today, Bill Clinton is embroiled in his own, new scandal. But even in the midst of THAT, nothing he's getting from the public is anywhere near the venom and bile that is still being directed at Monica, who was guilty of nothing more than being young, falling for a powerful man, and trusting a person she thought was a friend. For that, she has been America's Jezebel since the 90's.And I'm not giving myself a pass. I was part of the ridicule for a long, long time. I grew up, and am ashamed of my part in it.Since then, she has become an outspoken activist and public speaker, and she's really just an amazing human being.

#20 How Were People Okay With This? Britney Was 16/17 Years Old When She Did This Music Video. Hollywood Is Beyond Disgusting

#21 Playboy Products (Stationery, Folders) Were Once Sold At Stores, Including During Back To School Season. They Were Sometimes Displayed Near Childrens Brands. More Info In Description

#22 Billy Murray Harassing Geena Davis On Live TV

#23 Pop Russian Duo T.A.T.U Were 14 Being Sexualized And Exploited While Also Being Portrayed As A Lesbian Couple Which They Weren’t Which Plays Into Fetishization

#24 Bad Parenting: Drew Barrymore’s Childhood. She Was Up In Studio 54 Clubbing And Parties With Her Mom At Age 11

#25 The Concept Of "Hooters" As A Whole

#26 In The 2008 Movie Pineapple Express Seth Rogan’s 25 Year Old Character Is A Dating A Girl In High School

#27 Girl Orientated Magazines vs. Boy Oriented Magazines

#28 You Wanna Talk Cultural Appropriation? Beyonce In Hymn For The Weekend

Not forgetting that Beyonce also appeared as the Hindu deity Kali in her Grammy Performance.

#29 An Episode Of My Strange Addiction Mocks And Makes A Spectacle Of A Woman Who Seems To Be Neurodivergent And Has A Special Interest In Puppetry And Ventriloquism

A disclaimer… Yes- I know that the people featured on the show consented to being on the show. Despite this, the way the show is presented makes a mockery and spectacle of subjects of the show. A recent episode I watched spurred me to make this post. The supposed therapists or family members interviewed on the show don’t help either because they don’t seem to really understand the root of the cause or try to be compassionate. A lot of the people featured on the show either experienced trauma that they’re trying to heal from or seem to have undiagnosed neurodivergence.

#30 2015 Film Duff “Designated Ugly Fat Friend “ - Expect She Wasn’t Fat Or Ugly…

#31 Jim Carey Forcibly Kissing 19 Year Old Alicia Silverstone At The MTV Movie Awards

Feel like this doesn't get called out enough.

#32 The Repeated Comments Cinemasins Made About Young Emma Watson

#33 That Time SNL Sexualized Hermione From Harry Potter

#34 Emmy Rossum Was 17 Irl Making Out With Two Men In Their 30s In Phantom

#35 So Much About This Is Surface Level ‘Wwwowt?!’ But I’m Doing A Deep Dive And Did You Know These Women Didn’t Even Get Paid To Do This Show?

Second- I’m rewatching the Girls Next Door and listening to the Girls Next Level Podcast that Holly and Bridget made doing their first ever rewatch of the show since it aired.I knew the show was problematic just on the surface but the underlying treatment and grooming of these women is worse than I thought. They didn’t even get credits or paid until much later- they were never even asked if they wanted to be on the show or sign contracts- it was just assumed that they would comply.If anyone needs a rabbit hole to go down- it’s good one.

#36 I Think About This Show A Lot, Who Green Lit This Concept 💀

#37 Anyone Remembers The Swan Reality Show?

#38 Heart's Ann Wilson Was Called And Considered Fat During The 1980's

#39 Have We Discussed Steve Urkel?

And how he frequently stalked Laura, when she put her foot down (rightfully so), and the sad “awww” music would play and we’d all feel bad for him? He’d full on kiss her, pressure her, he was the definition of obsessive. I know they ended up together in the end but … I always think about that show and get the heebie jeebies now. We really felt badly for him

#40 This Scene In Mean Girls Being Played For Laughs

#41 How Did This Even Air?

Original Article on Source

Source: “AOL Entertainment”

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“Should’ve Been Enough To Put Him Behind Bars”: 41 Pop Culture Moments And Trends That Aged Poorly

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