 In an interview with the San Francisco Chronicle , Damon revealed that he was asked to appear on the show by Sean Hayes , a friend of Damon 's and the actor that plays Jack on Will & Grace . Damon enjoyed the idea for the episode and agreed to appear on the show . He commented that it was easy for him to get into character because he had previously played a gay character in the film The Talented Mr. Ripley ( 1999 ) . Following his appearance , Damon told the Chicago Sun @-@ Times in June 2002 that he would like to come back and guest star . 
