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Applegate also guest-starred on two episodes of "Friends", in the ninth (2002) and tenth (2003) seasons, titled "The One with Rachel's Other Sister" and "The One Where Rachel's Sister Babysits" as Amy Green, Rachel Green's (Jennifer Aniston) younger sister. She won the 55th Annual Prime Time Emmy Award for Best Guest Actress in a Comedy for her performance in "The One with Rachel's Other Sister". On the silver screen, she portrayed TV anchorwoman Veronica Corningstone in the 2004 films "Anchorman: The Legend of Ron Burgundy" and the DVD bonus film "Wake Up, Ron Burgundy: The Lost Movie" (an alternative film comprising alternate takes and deleted scenes and story elements).

In addition to her screen work, Applegate has performed on stage in such productions as "The Axeman's Jazz", "Nobody Leaves Empty Handed", and "The Runthrough", as well as John Cassavetes' "The Third Day" (co-starring Gena Rowlands). In 2004, she debuted on the Broadway stage playing the title role of Charity Hope Valentine in a revival of the 1966 musical Sweet Charity. She eventually took home the 2005 Theatre World Award and was nominated for a 2005 Tony Award for Best Actress in a Musical.