Black Side of The Second City

Celebrating The Second City’s amazing black performers through the years

At Woolly, we’re so proud to be hosting BLACK SIDE OF THE MOON — a powerful, political all-black show — in the current moment. But we also simply love having this incredible cast here at Woolly, making us laugh every single night and reminding us of all the good that can still happen in a chaotic world. In that spirit, we want to celebrate the black comedians of Second City’s past, present, and future. Here are some of our favorite comedic moments brought to you by Second City performers of color. Try not to drink anything while watching the clips below — whatever it is will end up all over your computer screen.

Tim Meadows

The legendary Tim Meadows was a Second City Mainstage staple from 1989 to 1991, but you probably know him best from his stint on SNL and/or his turn as Leon Phelps, THE LADIES MAN. They don’t make radio shows like this anymore.

Jerry Minor

Jerry Minor began doing sketch comedy and standup in Detroit before moving to Chicago to join the Second City nerve center in the 90s. But you’ve also seen him on Unbreakable Kimmy Schmidt, Community, and Mr. Show with Bob Odenkirk and David Cross (above).

Holly Walker

Holly Walker was hilarious as a correspondent and writer on The Nightly Show with Larry Wilmore, and we can’t wait to see what she does next.

Niccole Thurman

Niccole Thurman appeared in our 2015 show LET THEM EAT CHAOS, and absolutely crushed it! Her videos with the comedy group It’s Megan are definitely worth a watch, too.

Sam Richardson

If you watch VEEP, you already know — Second City alum Sam Richardson is one of the funniest actors on an absolutely stacked list of comedians rounding out this ensemble cast.

Keegan Michael-Key

Come on, you didn’t think we were going to leave Key out of this, right? Enter the rabbit hole of Key & Peele YouTube videos at your own peril — we hope you have a lot of time to kill!