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    Updated on Aug 25, 2020. Posted on Aug 22, 2020

    16 Times Teen Dramas Snuck In The Wildest Guest Stars

    Remember when Dan and Vanessa had a threesome with Hilary Duff?

    1. When Pete Wentz just casually strolled into town and dated 17-year-old Peyton on One Tree Hill.

    The WB

    I cannot emphasize how much I hate this storyline.

    2. When Gavin DeGraw kept popping up because he just happened to be in Tree Hill on One Tree Hill.

    Gavin and Peyton
    The WB

    We get it, he sings the theme song.

    3. When Hilary Duff played Vanessa's roommate and had a threesome with her and Dan on Gossip Girl.

    The CW

    I honestly couldn't remember if this really happened. Unfortunately, it did.

    4. And when Ivanka Trump and Jared Kushner showed up at a party on Gossip Girl??

    Lily thanks them for coming and Jared says it's a pleasure to be there
    The CW

    Are...are Lily and Rufus friends with them?

    5. When Naomi literally dissed Kim and Khloé Kardashian on 90210.

    Naomi tells Kim that whenever she's on "Who Wore It Best" she votes for the other girl
    The CW

    Want some ice for that burn, Kim?

    6. And when Adrianna took JOE JONAS as her date for a red carpet event on 90210.

    The CW

    7. When Sav dated Keke Palmer on Degrassi: The Next Generation.

    Sav asks why a famous singer would want to date a regular guy like him and Keke says he's special
    TeenNick

    8. And when Vanessa Morgan played Dallas's ex-girlfriend named...Vanessa on Degrassi: The Next Generation.

    TeenNick

    I know this was before she was on Riverdale, but it still catches me off-guard to rewatch Degrassi and see her.

    9. When Demi Lovato briefly played Santana's girlfriend Dani on Glee.

    Fox

    10. And when Britney Spears appeared in everyone's dreams in the "Britney/Brittany" episode of Glee.

    Britney Spears in a Cheerios uniform
    Fox

    This episode was ICONIC, though. It actually kind of makes me want to go to the dentist.

    11. When Adam Lambert appeared as himself on a Halloween special episode of Pretty Little Liars.

    Adam Lambert performing a concert in the episode
    The CW

    12. When Paris Hilton briefly played Logan's girlfriend Caitlin on Veronica Mars.

    Caitlin on her scooter alongside Logan
    UPN

    13. And when Michael Cera popped up as Veronica's college tour guide on Veronica Mars.

    Michael Cera a frat party with Veronica and Wallace
    UPN

    14. When Seth Rogan guest-starred as some loser named Bob who said he and Audrey "porked" on Dawson's Creek.

    The WB

    Seth showing up was random, but it was a nice little Freaks and Geeks reunion!

    15. When Shailene Woodley played a young Kaitlin Cooper on The O.C.

    young Kaitlin posing with Marissa and their dad
    Fox

    This was, of course, before she went to boarding school and inexplicably aged six years.

    16. And finally, when Chad Michael Murray appeared as an evil cult leader on Riverdale.

    Edgar stands up and claps rhythmically at the school musical
    The CW

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