Jon Glaser Represents 300 Years of American Tyranny at The Second City in 1995

Prepare for Tax Day with This 2007 Clip from The Second City

The Tea Party Sings About Healthcare and Wiretapping at The Second City in 2010

Amber Ruffin Sings About Why “It’s Good to Be Black” at The Second City in 2007

Brian Gallivan and Matt Craig Sing the “White Guys” Song at The Second City in 2005

Claudia Wallace and Antoine McKay Magically Solve White People’s Problems at The Second City in 2005

Check Out Some Clips of ‘Detroiters’ Stars Tim Robinson and Sam Richardson in Their Second City Days

The Second City Tackles Immigration Through The Power of Song in 2006

Katie Rich Leads an Improv Scene for the Audience’s Highest Bidder at The Second City in 2012

Watch Some Classic Clips of Amy Sedaris, Stephen Colbert, and Paul Dinello at The Second City