The Showtime comedy series Black Monday, follows the motley crew of employees at The Jammer Group in the year leading up to “Black Monday,” the worst stock market crash in Wall Street history. One of those employees, the young, wide-eyed Blair, is played by Tony Award-nominee Andrew Rannells. We recently sat down with Rannells to talk about two things in pop culture that always make him laugh: the 1986 Tom Hanks/Shelley Long comedy The Money Pit, and 30 Rock.