From Jimmy’s Woodlawn Tap to The Second City: How a South Side Bar Sparked a Comedy Revolution

Long before “Live from New York, it’s Saturday night!” became a national ritual, a different kind of magic was happening in a cramped Chicago cabaret. It was 1959, and a trio of visionaries — Paul Sills, Howard Alk, and Bernie Sahlins — cracked open a revolution. They called it The Second City, a scrappy experiment born from the ashes of the Compass Players, a University of Chicago–adjacent troupe that used improvisation not just to make people laugh, but to make them think.

The roots ran deep. Sills’ mother, Viola Spolin, had developed “theater games” — radical exercises that invited actors to play, listen, and react. Her methods became the DNA of modern improv. Out of that foundation, The Second City grew like wildfire, mixing satire, spontaneity, and sharp political wit into a kind of comedy America had never seen before.

The opening night on December 16, 1959, at 1842 North Wells Street, was small but seismic. Onstage, performers like Severn Darden, Barbara Harris, Mina Kolb, Paul Sand, and Eugene Troobnick ripped through sketches that took aim at politics, pop culture, and the human condition — with no safety net and no punchline in sight.

What started as an underground experiment became the beating heart of Chicago’s creative scene, a proving ground that would send wave after wave of talent into the world. From Mike Nichols and Elaine May to John Belushi, Gilda Radner, Bill Murray, Tina Fey, and Keegan-Michael Key, the alumni list reads like a comedic Hall of Fame.

The Second City didn’t just make people laugh — it redefined what comedy could be. It gave voice to rebellion, intellect, and absurdity in equal measure. And 65 years later, its influence still echoes across every sketch stage and late-night screen that dares to improvise.

Because if you trace today’s comedy back to its source, all roads still lead to Chicago — and that smoky cabaret where three dreamers turned laughter into art.

For more Stories From The 78, follow @tombarnas78 on Instagram and @storiesfromthe78 on TikTok.