The Second City

The Second City chose its self-mocking name from the title of a series of articles about Chicago by A. J. Liebling, published in The New Yorker in 1952, also published in book form as a collection the same year. In summer 1955, at The Compass bar in Hyde Park, University of Chicago students, led by David Shepherd and Paul Sills, calling themselves Compass Players, began a "commedia dell'arte", based on professional theater games taught by Viola Spolin, who was Sills's mother. They soon began performing occasional shows on the Near North Side. On December 16, 1959, The Second City's first revue show premiered at 1842 North Wells Street, with Sills's former wife and Compass Player Barbara Harris singing "Everybody's in the Know". Admission was $1.50 (equivalent to $17 in 2025). Sahlins and Sills flipped burgers in the kitchen.

Sahlins, Sills, and Howard Alk had founded the theater, in 1959, as a place where scenes and stories were created with improvisation, using techniques that grew out of Spolin's innovative teachings, later known as Theater Games, with Sills as its director. The cabaret theater comedy style of the Second City tended towards satire and commentary on social norms, and political figures and events.

In 1961, the theater sent a cast to Broadway with the musical revue, From the Second City, directed by Sills and earning Tony Award nominations for ensemble members Severn Darden and Barbara Harris. The company moved a few blocks south, to 1616 North Wells, in 1967. Eventually, the theater expanded to include three touring companies and a second resident company, and now fosters a company devoted to outreach and diversity.

In 2020, during the protests following the murder of George Floyd, The Second City faced several criticisms regarding racism. The CEO, Andrew Alexander, resigned after accusations of institutional racism from former performers and an alumnus were made. Accusations and allegations were also made on social media, triggering further leadership resignations. A notable criticism came from Second City alumnus Dewayne Perkins, who alleged that the institution initially refused to host a benefit show for Black Lives Matter unless half of the proceeds also went to the Chicago Police Department. In response to these issues, The Second City instituted changes, including the formation of a steering committee comprising representatives from BIPOC, Latinx, and LGBTQIA+ communities to foster inclusivity and diversity.

In October 2020, The Second City was put up for sale by Alexander and co-owner D'Arcy Stuart. In January 2021, The Second City and Saturday Night Live paired up to launch a new training scholarship for diverse, upcoming talent. In February 2021, ZMC, a New York City-based private equity investment firm, purchased The Second City.

In 2022, The Second City announced its expansion to New York with its new location in Williamsburg, Brooklyn. The nearly 12,000-square-foot (1,100 m2) entertainment complex at 64 N. 9th Street comprises two cabaret-style live theaters, seven Training Center classrooms, and a full-service restaurant and bar. The Second City New York opened to the public on November 16, 2023, marking a significant expansion of the institution into a new geographic region.