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Alright, friends! Today we're taking a wild stroll down memory lane to look at some super bizarre pop culture moments that people actually thought were okay. Think sketchy TV shows, weird celeb stuff, and random crazy trends from back in the day that make us go, "Wait, what?!" Ready? Let's dive in!

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#1

Toddlers Wearing Totally Sexist Clothes? Yep, That Happened

Toddlers Wearing Totally Sexist Clothes? Yep, That Happened

Crafty-Bat-9237 Report

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    #2

    R. Kelly Married A 15-Year-Old Aaliyah When He Was 27 – Yikes!

    R. Kelly Married A 15-Year-Old Aaliyah When He Was 27 – Yikes!

    AdrianaLaServing Report

    Okay, this one’s a big nope. Back in the day, R. Kelly married Aaliyah when she was just 15 and he was 27. The marriage certificate even lied about her age! People saw it and went, “Hmm, weird,” but still jammed out to their music. Fast forward, this was just the creepy tip of the iceberg. Not cool, guys.

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    #3

    Monica Lewinsky: From Public Punchline to Total Badass

    Monica Lewinsky: From Public Punchline to Total Badass

    Clinton White House Report

    Monica had a thing with the most powerful guy around, and instead of the dude catching heat, she became the world’s favorite scapegoat. Radios, shows, you name it - they roasted her nonstop. Now? She’s out here smashing it as an activist and totally owning her story. Take that, haters!

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    #4

    Drew Barrymore Was Partying At Studio 54... At 11 Years Old!

    Drew Barrymore Was Partying At Studio 54... At 11 Years Old!

    RookieTaylor Report

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    #5

    Billy Wyman Dated A 14-Year-Old And Married Her At 18 – Wait, What?

    Billy Wyman Dated A 14-Year-Old And Married Her At 18 – Wait, What?

    R0ttenStrawberry Report

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    #6

    Bridalplasty: A Plastic Surgery Contest You Won't Believe Was A Thing

    Bridalplasty: A Plastic Surgery Contest You Won't Believe Was A Thing

    Proper-Ad-8829 Report

    Imagine a reality show where engaged ladies compete for plastic surgery and a dream wedding. Yep, that was 'Bridalplasty' - think wine tastings leading to botox and boob jobs as prizes. The groom sees his bride’s new look for the first time at the wedding. Talk about pressure!

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    #7

    Ann Wilson from Heart Got Called Fat Back in the 80’s? Seriously?

    Ann Wilson from Heart Got Called Fat Back in the 80’s? Seriously?

    TheGoldDigga Report

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    #8

    Wilmer Valderrama’s Dating History: Teens Beware!

    Wilmer Valderrama’s Dating History: Teens Beware!

    L. Cohen/gettyimage Report

    Here’s a quick recap: He dated Mandy Moore at 20 when she was 16, Lindsay Lohan at 24 when she was 17, and Demi Lovato at 29 when she was 17. That’s one sketchy dating track record! No wonder folks joke if 'That 70s Show' is cursed.

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    #9

    Russell Brand, Katy Perry, and Justin Bieber Walk Into a Picture... And It's Uncomfortable

    Russell Brand, Katy Perry, and Justin Bieber Walk Into a Picture... And It's Uncomfortable

    Jeff Kravitz/AMA2010/gettyimages Report

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    #10

    25-Year-Old Ashton Kutcher Talking About 15-Year-Old Hilary Duff? Ew.

    25-Year-Old Ashton Kutcher Talking About 15-Year-Old Hilary Duff? Ew.

    Noonyezz Report

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    #11

    Bill Murray Harassed Geena Davis On Live TV? Uh, No Thanks.

    Bill Murray Harassed Geena Davis On Live TV? Uh, No Thanks.

    deleted Report

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    #12

    Khloe Kardashian Walked Four Black Women On Leashes… Wait, What?

    Khloe Kardashian Walked Four Black Women On Leashes… Wait, What?

    Michael Caulfield Archive/gettyimages Report

    Back in 2003, Khloe showed up to a Halloween party dressed as a pimp and walked four Black women on leashes. No one batted an eye then, but fast forward to 2022 and, yep, people were NOT happy.

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    #13

    Paul Walker Dated a 16-Year-Old When He Was 33... Hmm.

    Paul Walker Dated a 16-Year-Old When He Was 33... Hmm.

    Netflix Report

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    #14

    Remember That Time Russell Brand Posted a 4 AM Pic of Katy Perry?

    Remember That Time Russell Brand Posted a 4 AM Pic of Katy Perry?

    abussinessman Report

    Imagine living with someone who snaps pics of you at the crack of dawn and throws it on the internet. Yeah, Russell Brand did that.

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    #15

    Steve Urkel: The King of Unwelcome Obsession?

    Steve Urkel: The King of Unwelcome Obsession?

    Status-Visit-918 Report

    Remember how Steve kept stalking Laura? Whenever she said no, sad music played, and we all felt sorry for him. Creepy? Yep! But somehow we were rooting for him anyway. TV logic, am I right?

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    #16

    Russian Pop Duo T.A.T.U: Teen Girls, Sexualized and Misrepresented

    Russian Pop Duo T.A.T.U: Teen Girls, Sexualized and Misrepresented

    R0ttenStrawberry Report

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    #17

    Girl Magazines Vs Boy Magazines: Like, What Even?

    Girl Magazines Vs Boy Magazines: Like, What Even?

    AdrianaLaServing Report

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    #18

    Rolling Stone Called Lindsay Lohan 'Hot, Ready, and Legal' at 18—Weird Much?

    Rolling Stone Called Lindsay Lohan 'Hot, Ready, and Legal' at 18—Weird Much?

    icey_sawg0034 Report

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    #19

    Remember The Swan? A Reality Show Where They Took People and Transform—Like, Literally.

    Remember The Swan? A Reality Show Where They Took People and Transform—Like, Literally.

    PeachwoodArts Report

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    #20

    Jim Carrey Forcibly Kissing Alicia Silverstone at the MTV Movie Awards—Cringe Alert!

    Jim Carrey Forcibly Kissing Alicia Silverstone at the MTV Movie Awards—Cringe Alert!

    MTV Report

    This moment creeps under the radar but seriously shouldn’t! Consent is EVERYTHING.

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    #21

    Justin Timberlake’s 2004 Janet Jackson Wardrobe Malfunction—Major Backlash Ensued

    Justin Timberlake’s 2004 Janet Jackson Wardrobe Malfunction—Major Backlash Ensued

    KMazur/gettyimages Report

    When Justin ripped Janet’s costume, she got blacklisted big time. Talk about unfair!

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    #22

    Big Rhonda on That ’70s Show Was Treated Like She Was 500 Pounds (She Wasn’t)

    Big Rhonda on That ’70s Show Was Treated Like She Was 500 Pounds (She Wasn’t)

    b-nnies Report

    Remember how everyone acted like Big Rhonda was massive when she was just kinda... bigger than the other girls? TV was ruthless with their ‘fat joke’ obsession. Not cool.

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    #23

    CinemaSins and Their Never-Ending Jabs at Young Emma Watson

    CinemaSins and Their Never-Ending Jabs at Young Emma Watson

    Nickpicker96 Report

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    #24

    The Entire Idea of ‘Hooters’—Yeah, Let’s Not.

    The Entire Idea of ‘Hooters’—Yeah, Let’s Not.

    delphiedith Report

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    #25

    Playboy Stationery Sold Near Kids’ School Supplies? Wait, What?!

    Playboy Stationery Sold Near Kids’ School Supplies? Wait, What?!

    feminismandpancakes Report

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    #26

    Beyoncé as Hindu Deity Kali? Cultural Appropriation Alert!

    Beyoncé as Hindu Deity Kali? Cultural Appropriation Alert!

    Coldplay Report

    Beyoncé’s Grammy performance had her channeling the Hindu deity Kali. Some folks loved it; others? Not so much.

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    #27

    Girls Next Door: The Untold, Unpaid Drama Behind the Scenes

    Girls Next Door: The Untold, Unpaid Drama Behind the Scenes

    Titsoffwork Report

    Those ladies? They weren’t getting paid or even asked if they wanted to be on the show at first. Yikes. Watching the rewatch of this show is like opening a big ol’ can of messy worms.

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    #28

    ‘Black. White.’: Families Swapping Races in 2006 Reality TV?

    ‘Black. White.’: Families Swapping Races in 2006 Reality TV?

    AdrianaLaServing Report

    This 2006 reality show had two families transforming to look like each other’s race. Produced by Ice Cube, it even snagged an Emmy for makeup. Wild, right?

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    #29

    Friends and Others: Where Did All the Fat Jokes Come From?

    Friends and Others: Where Did All the Fat Jokes Come From?

    CapacityBuilding Report

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    #30

    Joel Madden Dated 16-Year-Old Hilary Duff When He Was 25—Yikes

    Joel Madden Dated 16-Year-Old Hilary Duff When He Was 25—Yikes

    Evan Agostini /gettyimages Report

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    #31

    2015 Movie 'DUFF' Called Someone The 'Designated Ugly Fat Friend'–But She Was Definitely Not Ugly or Fat

    2015 Movie 'DUFF' Called Someone The 'Designated Ugly Fat Friend'–But She Was Definitely Not Ugly or Fat

    ufocatchers Report

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    #32

    Britney Was 16/17 When She Did This Music Video—Hollywood, Seriously?

    Britney Was 16/17 When She Did This Music Video—Hollywood, Seriously?

    Falcon_Gray Report

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    #33

    Gwen Stefani’s Harajuku Girls: Silent Props or What?

    Gwen Stefani’s Harajuku Girls: Silent Props or What?

    Fox/gettyimages Report

    During her L.A.M.B era, Gwen toured with Asian women who barely spoke - a little spooky, and kinda unsettling. Once the album cycle ended, poof, they vanished. Hmmm.

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    #34

    'My Strange Addiction' Made Fun of a Woman With a Puppetry Hobby—Not Cool

    'My Strange Addiction' Made Fun of a Woman With a Puppetry Hobby—Not Cool

    TLC Report

    Sure, people consented to be on the show, but it sure looked like they were mocking someone who might be neurodivergent and just really into puppets. Not the kind of vibe we want.

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    #35

    That Time SNL Sexually Objectified Hermione Granger—Yikes!

    That Time SNL Sexually Objectified Hermione Granger—Yikes!

    Heart_breakerr Report

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    #36

    How Did This Even Get On TV? Seriously Asking.

    How Did This Even Get On TV? Seriously Asking.

    becauseimhappy24 Report

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    #37

    In 'Pineapple Express,' Seth Rogen’s 25-Year-Old Dates a High Schooler—Wait, What?

    In 'Pineapple Express,' Seth Rogen’s 25-Year-Old Dates a High Schooler—Wait, What?

    Columbia Pictures Report

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    #38

    Taylor Swift and Conor Kennedy’s Relationship: 1989 Meets 1994 in 2012

    Taylor Swift and Conor Kennedy’s Relationship: 1989 Meets 1994 in 2012

    taylorswift , jconorkennedy Report

    Taylor, born in ’89, dated teenage Conor from the famous Kennedys, born 1994, back in 2012. She even picked up his school notes and crashed events uninvited. Talk about a Twilight Zone romance.

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    #39

    This TV Show Concept? I Still Can’t Believe They Said Yes.

    This TV Show Concept? I Still Can’t Believe They Said Yes.

    Forttomato Report

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    #40

    Emmy Rossum Was 17 Making Out with Guys in Their 30s in ‘Phantom’? Ew.

    Emmy Rossum Was 17 Making Out with Guys in Their 30s in ‘Phantom’? Ew.

    Ok_Caterpillar_6689 Report

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    #41

    That Scene in ‘Mean Girls’ Played for Laughs? Uh, Not Funny!

    That Scene in ‘Mean Girls’ Played for Laughs? Uh, Not Funny!

    R0ttenStrawberry Report

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