Upon iO's founding, in 1983, with partner Del Close, she began teaching Harold to many students in the Chicago theater community.
In February 2018, she made the decision to close the theater citing the reasons as the neighboring nightclub and lack of attendance.
[1][2][3] She and Close co-authored the book Truth in Comedy: The Manual of Improvisation with editor Kim "Howard" Johnson in 1994.
In 2017, the theater reopened in the Clyborn North Area across from a Whole Foods flagship store, and next to VIPs strip club.
In 2020 during a forced shutdown due to the COVID-19 pandemic and a targeted racial justice outcry, she closed the only remaining Chicago location.
[10] This resulted in a sense of shared community that was often missed at already established comedy clubs such as Second City which were for performers that were already notable.
Since he was an admitted drug addict who had lost his job at the acclaimed Second City in 1982 not many people welcomed him into their comedic bubble.
[11] On Halpern's side of things, having Close be a part of the iO legitimized her theater and helped her learn more about improv as an art form.
[11] After years of working together, Close and Halpern decided to establish the iO (originally called the ImprovOlympic) in a more permanent location in 1995 by Wrigley field.
Although they lost one of their largest assets, Halpern continued to make major strides in producing some very notable alumni including: Amy Poehler, Tina Fey, Jack McBrayer, Neil Flynn, Adam McKay, Chris Farley, and Mike Myers.
[10][14] Eventually the theater rose to such acclaim that the iO became a staple stomping ground for Lorne Michaels in recruiting comedians to work for Saturday Night Live.
[14] On top of the insurmountable amount of debt that the theater took on, Halpern was criticized by the QBIPOC community pretty heavily .
[15] Halpern listed the building on 1501 N. Kingsbury Street, a prime real estate location in Chicago, for sale in the fall of 2020.
She understands that the trademark she has built for the company is highly reputable and hopes that whoever buys the building also considers taking the brand as well as the location.