Katie Holmes (Joey Potter), Then: Dawson's Creek was Holmes' first major role in Hollywood. She famously turned down the chance to fly out to LA for a callback because she was starring in her school's production of Damn Yankees at the time. Ultimately, of course, she got the part anyway. As Joey, she was at the center of one of the most hotly contested TV love triangles ever: Team Dawson (James Van Der Beek) vs. Team Pacey (Joshua Jackson, whom she dated in real life). Team Pacey won out in the end, but to some fans, Dawson will always be her soul mate.
Like Van Der Beek, Holmes had a few edgier film roles during the show's run, with parts in Disturbing Behavior, Go, Teaching Mrs. Tingle, Abandon, Phone Booth, and the acclaimed Pieces of April. (Photo via Getty Images)