> In 2000, Jimmy Fallon performed in blackface on Saturday Night Live, imitating former cast member Chris Rock.
> Jimmy Kimmel donned black paint over his body and used an exaggerated, accented voice to portray NBA player Karl Malone on The Man Show in 2003.
> In 2007, Sarah Silverman performed in blackface for a skit from The Sarah Silverman Program.
I don't think many people really realized blackface was problematic until sometime after 2007. Twitter started in 2006, so I imagine awareness improved in part due to twitter.