Chuck Sklar joined me to discuss his birth town; the Cubs and Blackhawks; his first memory of watching the 1968 Democratic National Convention; Captain Nice; Iowa comedians / comedy writers Harper Steele, Higgins Boys & Gruber; writing sketches for Toby Huss's comedy troupe; starting standup; being introduced as a great writer; moving to Boston from Chicago; callbacks; appearing on Evening at the Improv; writing for Friday Night Videos and Bill Maher; getting hired on Conan and becoming head monologue writer; writing for the Oscars and not knowing the movies; Chris Rock's bit about black people not caring about Oscar films; Chris's "accountants"; the Sean Penn - Jude Law dustup; playing David Copperfield; playing Osama bin Laden on "Louie"; writing for Saturday Night Special; getting hired on The Chris Rock Show; bringing his dry humor; famous sketches; his sketches with Mario Joyner; doing stand up on Conan; doing it now; his film script and the difficulties getting it made; going to SNL with Chris in 2014; working on the monologue and pitching a script that died at readthrough; working on tonight's monologue; Everybody Still Hates Chris