In 2000, Willis won an Emmy for Outstanding Guest Actor in a Comedy Series for his work on "Friends" (in which he played the father of Ross Geller's much-younger girlfriend). He was also nominated for a 2001 American Comedy Award (in the Funniest Male Guest Appearance in a TV Series category) for his work on "Friends". Also in 2000, Willis played Jimmy "The Tulip" Tudeski in "The Whole Nine Yards" alongside Matthew Perry. Willis was originally cast as Terry Benedict in "Ocean's Eleven" (2001) but dropped out to work on recording an album. In the sequel, "Ocean's Twelve" (2004), he makes a cameo appearance as himself. In 2005, he appeared in the film adaptation of "Sin City". In 2007, he appeared in the "Planet Terror" half of the double feature "Grindhouse" as the villain, a mutant soldier. This marked Willis's second collaboration with director Robert Rodriguez, following "Sin City".