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

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