Tina Fey- “Katie Couric Interviews Sarah Palin” Season 34 (2008)
Tina Fey
After graduating from the University of Virginia in 1992 with a degree in drama, Fey moved to Chicago to pursue her passion for improv. She joined The Second City in 1994, where she co-wrote and performed in the revue "Paradigm Lost." In 1997, Fey's career took a significant turn when she joined the writing staff of "Saturday Night Live" (SNL). By 2000, she began performing on the show and became the first female head writer in SNL's history. Fey also co-anchored the "Weekend Update" segment alongside Jimmy Fallon and later Amy Poehler, earning acclaim for her sharp wit and engaging delivery.
Seth Meyers
After graduating from Northwestern University, Meyers immersed himself in Chicago's comedy community, studying under iO co-founder Charna Halpern. Meyers' time at iO Theater not only honed his improvisational skills but also connected him with fellow comedians who would become significant collaborators in his career. This foundation seamlessly transitioned to his role at Saturday Night Live (SNL). Joining the SNL cast in 2001, Meyers' sharp wit and improvisational prowess quickly became evident. He ascended to the position of head writer in 2006 and co-anchored the "Weekend Update" segment alongside Amy Poehler, later continuing solo.
Seth Meyers - "Really?!? With Seth, Amy and Tina" Season 35 (2010)
Fred Armisen- “New Girlfriend” Season 41 (2016)
Fred Armisen
Fred Armisen began his comedy career at The Second City in Chicago, where he trained in improvisational comedy before moving to New York and joining the Upright Citizens Brigade theater. While Armisen was not officially part of Second City's mainstage cast, his early improvisational experiences were heavily influenced by the Chicago comedy scene. In 2002, Armisen joined Saturday Night Live as a cast member. His ability to blend improv with scripted material made him one of SNL's most distinctive and consistent performers during his tenure.
Vanessa Bayer
After graduating from the University of Pennsylvania, Bayer joined Second City and ImprovOlympic (now iO Theater). Her time in Chicago allowed her to develop her sharp comedic timing and character work, which ultimately helped her land a spot on SNL in 2010. Over her seven seasons on the show, she became known for her impeccable impressions, including Miley Cyrus, Rachel from Friends, and Jacob the Bar Mitzvah Boy, a recurring character that showcased her unique comedic style. Bayer’s bright, cheerful delivery and commitment to awkward humor made her a standout in both sketches and Weekend Update segments. Her performance earned her critical acclaim, and in 2017, she received an Emmy nomination for Outstanding Supporting Actress in a Comedy Series. She left SNL at the end of the 2016–2017 season as the longest-tenured female cast member at the time, leaving behind a legacy of sharp character work and infectious enthusiasm.
Vanessa Bayer - "Jacob the Bar Mitzvah Boy" Season 39 (2013)
Cecily Strong- “Girl You Wish You Hadn't Started a Conversation with on Christmas” Season 38 (2012)
Cecily Strong
Cecily Strong, a native of Illinois, began her comedy career at The Second City in Chicago, where she trained and performed with the theater's national touring company. In 2012, Strong joined Saturday Night Live as a featured player and quickly became a standout, known for her strong character work and impressions, including her memorable portrayal of Melania Trump. Strong was promoted to a full cast member in 2013 and became the longest-serving female cast members in SNL history, showcasing her ability to balance humor with emotion in a wide range of sketches.
Aidy Bryant
Aidy Bryant began her comedy career in Chicago, where she trained and performed at The Second City and with the Second City Touring Company. She joined Saturday Night Live in 2012 as a featured player. Bryant quickly became known for her impressive character work and impressions, including notable portrayals of figures like Sarah Huckabee Sanders. Over the course of her tenure, Bryant became a key player on SNL, recognized for her ability to balance humor with nuanced performances, and remained with the show until 2022.
Aidy Bryant - "Aidy B & Cardi B" Season 43 (2018)
Alex Moffat
Alex Moffat began his comedy career in Chicago, where he trained and performed at The Second City and with other local improv theaters. This foundation in improv led him to Saturday Night Live, where he joined the cast in 2016 as a featured player before being promoted to a full cast member. Moffat playing a wide range of characters, including his memorable portrayal of Joe Biden, which gained significant attention during the 2020 presidential election.
Alex Moffat “Guy Who Just Bought A Boat” Season 47 (2022)
Chris Redd
Chris Redd began his comedy career in Chicago, where he trained in improv and sketch at The Second City and iO Chicago, becoming a fixture in the city's vibrant comedy scene. His work in Chicago’s improv community, particularly his time at iO, helped shape his dynamic comedic style and improv skills. In 2017, Redd joined Saturday Night Live as a featured play. His most notable work on SNL included his impression of Kanye West, his portrayal of a variety of celebrity and political figures, and his ability to blend physical comedy with quick improvisation. Redd also showcased his versatility in recurring sketches like "Black Jeopardy!" and became known for his strong rapport with other cast members. Redd remained with SNL until 2022.
Chris Redd - "Seat Fillers" Season 47 (2022)
Michael Che “Colin Jost and Michael Che Swap Jokes” Season 49 (2024)
Michael Che
Michael Che began his comedy career in Chicago, where he was involved in the city’s vibrant improv scene, performing at The Second City and iO Chicago. His time in Chicago helped shape his sharp, observational comedy style and improv skills, which he later brought to Saturday Night Live (SNL) in 2014. Che joined the show as a writer and featured player, eventually becoming co-anchor of the Weekend Update segment alongside Colin Jost. Che's unique blend of humor, often addressing race, politics, and current events, brought a fresh dynamic to Weekend Update.