16. Reese Witherspoon
Jill Green – “The One With Rachel’s Sister” – S6E13 (first of two appearances)
Reese Witherspoon was famous for her work in movies, so it was surprising to see her showing up in a television series. Her only other television roles at that point had been in made-for-TV movies and the Return to Lonesome Dove mini-series. Her movie roles, however, were in films like Freeway, Election, and Cruel Intentions. One of her most popular characters, Elle Woods, came along after Witherspoon appeared on Friends as Jill Green, Rachel’s youngest sister.
Jill shows up at Rachel’s apartment in New York City after being financially cut off from their father, Dr. Leonard Green. Even though she’s determined to follow Rachel’s lead and make it on her own, Jill can’t seem to break her shopping addiction fueled by daddy’s credit cards. Ross and Jill end up flirting, but Jill dismisses Ross as “not the kind of guy you’d date.”
Rachel, in the process of defending her relationship with Ross, accidentally convinces Jill that Ross is worthy of a date so Jill asks him out. In an act of typical sibling rivalry, Jill taunts Rachel, closing the curtains to Ross’ apartment in order to make Rachel think that sexy times are in store.
The story picks up in the next episode, “The One Where Chandler Can’t Cry.” Jill uses Ross to get back at Rachel which leads to Ross and Rachel realizing they still have feelings for each other.