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