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    37 Pictures That Show Just How Strange The Years 2005–2009 Were

    From Claymates' ovaries shaking to everyone dressing like chimney sweeps.

    by ,

    1. The Sprouse twins dressed up as tiny, old-timey chimney sweeps.

    Gregg Deguire / FilmMagic

    2. The Jonas Brothers dressed up as hipster chimney sweeps.

    Eugene Gologursky / WireImage

    3. Ashley Tisdale in a full-on "Ashley Tisdale just robbed a Limited Too" ensemble.

    Frederick M. Brown / Getty Images

    4. All of this hair.

    Barry King / WireImage

    5. But Joe especially.

    Barry King / WireImage

    6. Whew, Joe (clearly he was BFFs with his flat iron).

    Dave Hogan / Getty Images

    7. Miley Cyrus posing with a cordless house phone so she could get it for free.

    Marsaili McGrath / Getty Images for Distinctive Assets

    8. Paris Hilton when she dated one of the Madden Brothers.

    Charley Gallay / Getty Images

    9. Hilary Duff when she dated the other Madden brother.

    Bryan Bedder / Getty Images

    10. Bruce Willis and Avril Lavigne walking the Kids’ Choice Awards red carpet together.

    Frazer Harrison / Getty Images

    11. Beyoncé proudly holding up a brick phone.

    Scott Gries / Getty Images

    12. Kim Kardashian West and Paris Hilton staring at a crying child.

    John Stanton / WireImage

    13. Kim staring at her boss, Paris, while they're both wearing Oktoberfest gowns.

    Thomas Niedermueller / Getty Images

    14. John Mayer and Taylor Swift happily ever after.

    Dimitrios Kambouris / Getty Images for Vevo

    15. Rihanna and Tweety Bird.

    Mathew Imaging / WireImage

    16. A bunch of people with some creepy-ass Susan Boyle masks.

    Jeff J. Mitchell / Getty Images

    17. You know, just Justin Bieber hanging out with Pete Wentz, Kristinia DeBarge, and Babyface...who were full-grown adults.

    Theo Wargo / Getty Images

    18. Rihanna and a little Justin Bieber.

    Theo Wargo / Getty Images

    19. The Jonas Brothers in full-on Ed Hardy drag.

    Frazer Harrison / Getty Images

    20. Zac Efron and the generic "15-year-old white kid from the suburbs who wears head-to-toe Hollister" haircut.

    Stephen Shugerman / Getty Images

    21. Billy Ray Cyrus getting it on with Minnie Mouse while Miley catches them in the act.

    Charley Gallay / Getty Images

    22. Jennifer Hudson, Jordin Sparks, Kelly Clarkson, Leona Lewis, Adele, and Miley Cyrus hanging out backstage at the 2009 VH1 Divas Live.

    Jeff Kravitz / FilmMagic

    23. Zooey Deschanel and Katy Perry back when everyone used to mistake them for each other.

    Jesse Grant / WireImage for Bluprint

    24. A "Claymate" with a shirt that says Clay Aiken makes her ovaries shake.

    Gregg Deguire / WireImage

    25. Borat casually hanging out in his mankini.

    Rick Nederstigt / Getty Images

    26. Kevin Federline and Britney Spears as a married couple.

    Matthew Simmons / Getty Images

    27. Steve Jobs holding up the epitome of mid-'00s technology, an iPod Classic — that is playing a video of a Desperate Housewives episode.

    Medianews Group / Getty Images

    28. Mandy Moore at New York Fashion Week with the Olsen twins.

    Peter Kramer / Getty Images

    29. Taylor Swift in a completely-not-staged photo op date with Taylor Lautner.

    Marcos Vasquez / BuzzFoto / FilmMagic

    30. Katherine Heigl holding a Zune at a Zune party.

    Michael Loccisano / FilmMagic for UPP Marketing

    31. The Pussycat Dolls dressed as if they work at a pirate-themed restaurant.

    Paul Hawthorne / Getty Images

    32. The Black Eyed Peas with the Pussycat Dolls.

    Dimitrios Kambouris / WireImage

    33. Bb Keke Palmer visting 106 & Park.

    Johnny Nunez / WireImage

    34. TV legends Drake Bell, Raven-Symoné, and Josh Peck.

    Frank Micelotta / Getty Images

    35. Kat McPhee at the launch party for the BlackBerry Curve.

    Jon Kopaloff / FilmMagic

    36. David Beckham looking as if he's trying to remember how to hold a phone while at the launch of the Razr 2.

    VCG / Visual China Group via Getty Images

    37. And finally, Pete Wentz showing off his T-Mobile Sidekick 3 and his perfectly flat-ironed emo side-swept bangs.

    Alexandra Wyman / WireImage for Tamie Peters & Christiaan McPherson Public Relations

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