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    Updated on Apr 23, 2020. Posted on Apr 23, 2020

    50 Pictures From The 2000s Of Celebs Who Probably Wouldn't Hang Out Together Nowadays

    Time to feel ~~nostalgic.~~

    1. I need to start with one of the top 10 best pictures I've ever seen: Beyoncé hanging out with Kelly Osbourne. I'm surprised this photo never became a meme.

    Jeff Kravitz / FilmMagic / Getty Images

    2. Jared Leto and My Chemical Romance's Gerard Way were totally inspiring fanfic.

    Kevin Mazur / WireImage / Getty Images

    3. Justin Timberlake and Evanescence singer Amy Lee just chillin'.

    Jesse Grant / Getty Images

    4. I was not expecting to see The Strokes' Julian Casablancas and Fab Moretti hanging out with Fergie and will.i.am. from the Black Eyed Peas, but hey, the aughts were a special era!

    L. Cohen / WireImage / Getty Images

    5. Here's Fall Out Boy posing with their buds, Beyoncé and Jay-Z.

    Jeff Kravitz / FilmMagic, Inc / Getty Images

    6. Paris and Nicky Hilton were casually making tons of teen girls jealous by getting super close to Chad Michael Murray.

    J. Vespa / WireImage for Harrison & Shriftm / Getty Images

    7. Lots to unpack here: it's Kim Kardashian hanging out with Cheetah Girls Adrienne Bailon (who dated Kim's brother Rob) and Sabrina Bryan, Evan Ross, Danity Kane's Aubrey O'Day, and Pussycat Dolls member Melody Thornton.

    Ben Rose / WireImage / Getty Images

    8. Lindsay Lohan partying with Kourtney and Kim Kardashian is everything I needed.

    Christopher Polk / Getty Images

    9. What a motley crew! That's Tommy Lee, Hayden Panettiere, Miley Cyrus, and Lance Bass.

    Kmazur / WireImage / Getty Images

    10. Few things are more 2000s than Tony Hawk, Good Charlotte's Benji and Joel Madden, and Jaime Pressly randomly hanging out.

    Jeff Kravitz / FilmMagic / Getty Images

    11. I was not expecting to see Paris Hilton and Kim Kardashian hanging out with Anton Yelchin (who died in 2016), but I'm into it.

    Stephen Shugerman / Getty Images

    12. My reaction to this pic of Johnny Knoxville catching up with Pharrell is the same as the photobomber's.

    E. Charbonneau / WireImage / Getty Images

    13. Yes, that's Boy Meets World's Blake Sennett (who played Joey the Rat) and Winona Ryder. They dated!

    Michel Dufour / WireImage / Getty Images

    14. Ben McKenzie and Zooey Deschanel are making me wish they would've made a quirky rom-com back in the day.

    Christopher Polk / FilmMagic / Getty Images

    15. It's the super nostalgic comedy trio of Jon Heder, Jack Black, and Will Ferrell!

    Jeff Kravitz / FilmMagic, Inc / Getty Images

    16. Here's James Van Der Beek and his ex-wife Heather McComb hanging out with Tara Reid and Carson Daly. Fun fact: Tara and Carson were engaged at one point!

    Kmazur / WireImage / Getty Images

    17. Three guys who you probably had posters of in your childhood bedroom: Riley Smith, Adam Brody, and Shane West.

    Jamie Mccarthy / WireImage / Getty Images

    18. Ben McKenzie and Amy Adams spending time together while promoting their movie, Junebug. This was right before Amy Adams became the Amy Adams.

    Alison Buck / WireImage / Getty Images

    19. Just two TV couples-turned-IRL-couples hanging out, NBD! Now I'm feeling nostalgic for those days when House's Jennifer Morrison and Jesse Spencer and The O.C.'s Adam Brody and Rachel Bilson were a thing.

    L. Cohen / WireImage / Getty Images

    20. J.C. Chasez, Aubrey O'Day, and Adam Brody spending time together didn't seem so bizarre at the time.

    Patrick Mcmullan / Getty Image

    21. Can we just talk about Avril Lavigne, Pink, Jennifer Lopez, and Lisa Marie Presley hanging out? Now I'm sad the pop stars didn't team up for a song.

    Jeff Kravitz / FilmMagic, Inc / Getty Images

    22. The 2000s Latina star power in this pic of Rosario Dawson, J.Lo, and Jessica Alba is incredible.

    Jeff Vespa / WireImage / Getty Images

    23. I'd give anything to go back in time and hang out with this messy crew of Anna Nicole Smith, Courtney Love, and Avril Lavigne.

    Kmazur / WireImage / Getty Images

    24. Vanessa Hudgens and Avril Lavigne?! WHAT?!

    Michael Buckner / Getty Images

    25. This pic of Usher and Hayden Christensen is everything.

    Kmazur / WireImage / Getty Images

    26. Natalie Portman and Soulja Boy got real close at TRL...

    Michael Loccisano / FilmMagic

    27. Snoop Dogg and Matthew Perry playing video games because, sure, why not.

    James Devaney / WireImage / Getty Images

    28. My queens Chloë Sevigny, Maya Rudolph, and Mary-Kate Olsen.

    Gregory Pace / FilmMagic / Getty Images

    29. Here's Natalie Portman and Lea Michele before the Glee days.

    Bruce Glikas / FilmMagic / Getty Images

    30. TV royalty Tina Fey, Lauren Graham, and Matthew Perry casually hanging out.

    John Shearer / WireImage / Getty Images

    31. Can we just talk about the teen movie star power here? I'm obsessed with Chloë Sevigny, Seth Green, Natasha Lyonne, Wilmer Valderrama, Macaulay Culkin, and Dylan McDermott promoting Party Monster.

    J. Vespa / WireImage / Getty Images

    32. My favorite gingers from my preteen years! It's Lindsay Lohan and Seth Green catching up while Macaulay Culkin is taking it all in.

    L. Cohen / WireImage / Getty Images

    33. I aspire to be cool enough to be part of this crew of Mandy Moore, Famke Janssen, Rashida Jones, and Maggie Gyllenhaal.

    Dimitrios Kambouris / WireImage / Getty Images

    34. Seeing Kim Kardashian and Pete Wentz together feels weird, but then again, she was in the "Thnks fr th Mmrs" music video.

    Barry Brecheisen / WireImage / Getty Images

    35. I'm obsessed with the diva power of this pic.

    Johnny Nunez / WireImage / Getty Images

    36. Seeing Demi Lovato and Pete Wentz spending time together at the Kids' Choice Awards is making me feel so nostalgic.

    Jeff Kravitz / FilmMagic / Getty Images

    37. I can't deal with this pic of Lindsay Lohan with Pete Wentz and Michelle Trachtenberg (who he dated!).

    Jeff Kravitz / FilmMagic / Getty Images

    38. Seeing Bam Margera hanging out with Simple Plan is taking me back to being an angsty kid.

    Scott Gries / Getty Images

    39. If my 14-year-old self had seen this pic of Jared Leto and Bam Margera, she would've flipped her shit.

    Scott Gries / Getty Images

    40. Look at all these teen TV stars! That's Topher Grace, Kristen Bell, Rachel Bilson, and Olivia Wilde.

    Kmazur / Getty Images

    41. I can't deal with Bono kissing Gwen Stefani's baby bump.

    Michael Caulfield Archive / Getty Images

    42. Just Kim Cattrall hanging out with Beyoncé and Jay-Z at a Rockets vs. Knicks game, as one does.

    James Devaney / WireImage / Getty Images

    43. I'm obsessed with the chaotic vibes from Kanye and Courtney hanging out.

    Michel Dufour / WireImage / Getty Images

    44. Rachel Bilson! Rihanna! Joel Madden and Nicole Richie before getting married! I cannot deal!

    Peter Kramer / Getty Images

    45. Lil Jon, Hilary Duff, and Jason Biggs!!!! WHAT?!

    Frank Micelotta / Getty Images

    46. This pic is a work of art: Pharrell pointing at Fred Durst's the Smiths T-shirt while hanging out with Paris Hilton.

    Mark Mainz / Getty Images

    47. The energy of this pic!!!!!! I want to know all the details of Prince William and Prince Harry partying with Diddy and Kanye.

    Tim Graham Photo Library via Getty Images

    48. Seeing Usher, Hilary Duff, and Tony Hawk at TRL is really taking me back.

    Kmazur / WireImage / Getty Images

    49. I wonder what Kim Kardashian would say about this pic of Paris Hilton cuddling up to Kanye West.

    Johnny Nunez / WireImage / Getty Images

    50. And finally, Jim Sturgess with Nat and Alex Wolff.

    Jemal Countess / WireImage

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