Nick has a fantastic conversation with Katie Rich, an incredible writer/performer who spent 6 seasons writing on "Saturday Night Live," exclusively working on Weekend Update. They talk about Katie's early life growing up on the Southside of Chicago (as a Cub fan!), her days working at "iO" with people like Charna Halpern and Cecily Strong, the time she spent of stage at Second City, and the tense and amazing years she spent writing jokes and working every week on Update. She talks about what it's like to be in the studio while Update is being performed and her jokes are being told, her favorite Update segments, what it was like to write during the insane political and news period that started in 2016, and the time she got to appear on stage with Bill Murray & the World Series Champion Chicago Cubs. Nick and Katie also talk a lot about baseball (and their shared love of the '93 Phillies), throwing up in LaGuardia Airport, getting great advice from George Wendt, and Katie's work in the world of animation. This is a must-listen interview with a hilarious and gifted writer who made wonderful and funny contributions to SNL. [EP37]