Madonna in her brief and incredibly random children's book author era.Dimitrios Kambouris / WireImage / Getty ImagesNick Lachey and Jessica Simpson posing with some off-brand MP3 players.Ludacris illegally downloading songs off of Napster.Avril Lavigne in a wee ole' top hat showing off the"Rock On" letters she put in her coat with white electrical tape.Frazer Harrison / Getty ImagesLeonardo DiCaprio kissing the cheek of a very enthusiastic Gisele Bundchen.
Cohen / WireImage / Getty ImagesTom Cruise prom posing with his then girlfriend Penelope Cruz.Frank Micelotta / Getty ImagesMandy Moore and Andy Roddick when they were briefly an item.J. Vespa / WireImage / Getty Images25.t.A.T.u. pretending to be lesbians.Paul Rudd taking pictures with a very tiny cellphone.J. Vespa / WireImage / Getty ImagesFreddie Prinze Jr. in his extremely 2003 Urban Outfitters graphic tee and Ashlee Simpson in her extremely 2003 knitted beanie cap.
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