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

Peter Grosz Plays a Professional Cuddler at The Second City in 2002

Paul Sand and Eugene Troobnick Become Phono Pals at The Second City in 1961

David Pasquesi and Jill Talley Prepare for Their Green Card Marriage at The Second City in 1990

Watch a Clip from Second City Toronto’s 15th Anniversary Special Featuring Martin Short

Spend a Day at the Office with Tim Robinson, Sam Richardson, and More in 2010

The Second City Prepares for Another Brutal Chicago Winter Through Song

Let Tim Baltz’s “Positive Guy” Help You Mentally Prepare for Thanksgiving

Amber Ruffin Shows Off Her Rap Skills at The Second City in 2007

When The Second City Got Political with Steve Carell, Tina Fey, Bob Odenkirk, and More

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