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Meet Rachel Dratch, The Second City’s 1996 NBA Superstar

Chicago’s City Councilman Candidates Square Off in a Debate at The Second City in 2012

Mary Sohn and Tim Baltz Meet for a First Date at The Second City in 2011

Spend Some Time with the Bro Golfers of The Second City in 2015

Amber Ruffin Plays a Very Wise Grandmother at The Second City in 2008

Mike Myers and Bonnie Hunt Make Some Important Decisions in Second City’s 1987 Pilot ‘110 Lombard Street’

Fred Willard Makes the Perfect ‘Teen Bandstand’ Host in This Second City Clip

Go Back to School with This 2007 Sketch from The Second City

Kevin Dorff Plays a Faithful Football Player at The Second City in 1999

Jason Sudeikis Shows the Power of Dance in the 2003 Second City Scene “Dirty Baghdad”

Take the Most Honest Driving Test Ever with Kevin Dorff and Scott Adsit at The Second City

Aidy Bryant Attends a Father/Daughter Dance at The Second City in 2012

Tina Fey, Kevin Dorff, Rachel Dratch, and More Have a Diplomatic Meeting at Second City in 1997

Stephen Colbert Hosts ‘The Jack Skanooni Show’ at The Second City in 1994

Embrace Your Anger with Bill Murray and the Second City Symphony of Social Criticism

Sam Richardson and Allison Bills Adjust to Life in America at The Second City in 2010

Stephen Colbert Plays the Worst Therapist Ever at Second City in 1994

Kevin Dorff and T.J. Jagodowski Enjoy Some Father/Son Bonding at The Second City in 1998

Second City Toronto Combines Two Theatrical Favorites in 1997’s “Glass Mamet”

Watch Horatio Sanz Spend His Saturday at a Wake in 1998