In June 2007 , she hosted the MTV Movie Awards . During her opening act , she commented on the upcoming jail sentence of Paris Hilton , who was in the audience , saying : " In a couple of days , Paris Hilton is going to jail . As a matter of fact , I heard that to make her feel more comfortable in prison , the guards are going to paint the bars to look like penises . I think it is wrong , too . I just worry she is going to break her teeth on those things . " In September 2007 , she appeared at the '' MTV Video Music Awards '' . Following the comeback performance of Britney Spears , Silverman mocked her on stage , saying : " Wow , she is amazing . I mean , she is 25 years old , and she has already accomplished everything she 's going to accomplish in her life . " In January 2008 , she appeared on '' Jimmy Kimmel Live ! '' to show Jimmy Kimmel , her boyfriend at the time , a special video . The video turned out to be a song called " I 'm Fucking Matt Damon " in which she and Matt Damon sang a duet about having an affair behind Kimmel 's back . The video created an " instant YouTube sensation . " She won an Primetime Emmy Award for Outstanding Original Music and Lyrics at the 60th Primetime Emmy Awards . Kimmel responded with his own video a month later with Damon 's friend Ben Affleck , which enlisted a panoply of stars to record Kimmel 's song " I 'm Fucking Ben Affleck " . On September 13 , 2008 , Silverman won a Creative Arts Emmy Award for writing the song " I 'm Fucking Matt Damon " . Silverman guest-starred in a second-season episode of the USA cable program '' Monk '' as Marci Maven . She returned in the sixth-season premiere and for the 100th episode . According to the audio commentary on the '' Clerks II '' DVD , director Kevin Smith offered her the role that eventually went to Rosario Dawson , but she turned it down out of fear of being typecast in " girlfriend roles " . However , she told Smith the script was " really funny " and mentioned that if the role of Randal Graves was being offered to her she " would do it in a heartbeat . " She appeared in '' Strange Powers '' , the 2009 documentary by Kerthy Fix and Gail O'Hara about cult songwriter Stephin Merritt and his band The Magnetic Fields . Silverman wrote a comic memoir , '' The Bedwetter : Stories of Courage , Redemption , and Pee '' , which was published in 2010
60th Primetime Emmy Awards
60th Primetime Emmy Awards
Sarah Silverman