Anita Hill is actually pretty conservative, which most people tend to forget...you are going to want a solidly left of center candidate to fill this spot.
Jimmy Kimmel is a comedian. There are many black women to consider for the Supreme Court. No need to try entertaining people with this momentous decision.
Why would she want to work along side the same man who sexually assaulted her, almost ruined her career and credibility, and still claims he didn't do it!? She's bigger than he will ever be.