The Wieners Circle opened for business in 1983. Sometime in the early 1990s Larry Gold, one of the proprietors, called a drunk and distracted customer an "asshole" in order to get his attention. This set off the late-night abuse culture of the restaurant. The atmosphere can range from playful to hostile. The language used by both the staff and customers during these hours is notoriously foul and aggressive. On the weekends, the establishment stays open as late as 5:00 am, drawing many drunken customers who have arrived from bars and clubs. The nightly tips are very high, and people have worked there for ten years or more. The location of the hot dog stand is just north of what used to be the Wrightwood Hotel. In 2008, the restaurant was briefly closed by health inspectors for not having hot running water where employees would wash their hands, and other food safety violations. The establishment has a history of political satire in its signage and advertising. In March 2016, the restaurant offered 3-inch "Trump footlong" hot dogs. In June 2017, they advertised "Paris Accord compliant covfefe". In March 2020, signage mocked the pardoning of Rod Blagojevich.
In media
One of the more famous employees is Roberta "Poochie" Jackson, who was featured in a 2007 episode of the Showtime television version of the Chicago Public Radio program This American Life, as well as an episode of Extreme Fast Food on the Travel Channel. In Chicago travel guides, The Wieners Circle is often extolled as a source for authentic Chicago-style hot dogs and its uniquely abrasive customer relations. Journalist Catherine Price listed The Wieners Circle in her book 101 Places Not to See Before You Die, calling it "a microcosm of segregation in Chicago", and commenting, "If our metric were 'places that make me sad about humanity,' late night at Wiener's Circle would have been at the top." The restaurant was featured in an episode of Insomniac with Dave Attell on Comedy Central in 2002. The restaurant is the setting for a truTVreality show. The Wieners Circle was featured in both radio and TV episodes of This American Life. The restaurant was the setting of a sketch featuring Jack McBrayer and Triumph, the Insult Comic Dog in the June 14, 2012 episode of the late night talk showConan, which was the last in a week of shows taped in Chicago. In the "Going Deep" episode of The Great Indoors Jack takes Eddie there to cheer him up after his divorce, only to have staffer Valerie unwittingly razzes Eddie about his divorce. Jack later sends Clark and Emma there as a prank, as they don't understand that the insults are part of the experience. In April 2020, during the COVID-19 pandemic, the Wieners Circle began producing a YouTube show called 'Wieners Circle TV'.
