Jenna (Jane Krakowski) wears blackface in Season 3, Episode 2, which was titled, “Consider In The Stars,” when Liz (Tina Fey) leaves city to attend jury obligation in Chicago, and on a flight, she thinks she met Oprah Winfrey. In the meantime, Jenna and Tracy (Tracy Morgan) are in a heated argument, debating whether or not Tracy can higher survive higher in society as a white girl, versus Jenna as a Black man. They “commerce locations” for a day, and Jenna paints her face black.
Season 5, Episode 10, which was titled “Christmas Assault Zone,” can be getting pulled. Liz helps Jack (Alec Baldwin) by means of an uncomfortable confrontation on Christmas Eve, whereas Jenna has a messy breakup along with her boyfriend, Paul L’Astname (Will Forte). Paul sees Jenna upset and invitations her to a dressing up social gathering wherein friends dressed as pop cultural phenomena. Paul clothes as Black Swan, and Jenna “mockingly” echos the sentiment and clothes as former Steelers participant, Lynn Swan… in blackface.