Second City (Chicago nickname)

Chicago, a large city in the American mid-west, was branded the United States's Second City after influential New Yorker writer A.J. Liebling applied this term to the city in 1925.^[1]

Over the years many other commentators agreed with Liebling, with Alson J. Smith writing of the Chicago art scene, in 1953, "that few if any countries have more than one dominant cultural center, and that in the United States New York is, and is likely to remain, that center.".^[2]

According to Daniel Hautzinger Chicagoans, could defy the put down as when "a group of young Chicago artists took the dismissive name as their own when they founded The Second City improv theater."^[3]

References

↑ Christopher Borrelli (2025-06-24). "Was A.J. Liebling right about Chicago? Decades after the New Yorker's 'Second City,' time for a second reading". Chicago Tribune. Retrieved 2026-01-14. Arguably nothing in 100 years of the New Yorker landed on Chicago with more oomph than A.J. Liebling’s infamous 1952 three-part profile of the city. No, wait, strike “arguably” — that I’m writing this piece soon after my colleague Rick Kogan’s piece on how Liebling gave Chicago another nickname and inspired a certain comedy troupe, that alone suggests Liebling got under this city’s skin with a precision few can claim.
↑ J. Weintraub (1993-07-29). "Why They Call It the Second City". Chicago Reader. Archived from the original on 2025-01-18. Retrieved 2026-01-14. In Chicago: The Second City Liebling saw such schizophrenic juxtapositions as being typical of Chicago boosters, who seemed to value quantity over quality and whose voices often rang as hollow as that of any pitchman defeated by the tawdriness of his goods.
↑ "Revisiting the Biting Articles That Branded Chicago the "Second City"". WTTW Chicago. 2022-12-15. Archived from the original on 2025-03-16. Retrieved 2026-01-14. Liebling was familiar with this form of Chicago boosterism. In his infamous articles, which gave Chicago the “Second City” nickname, he noted a “first-or-nothing psychology” amongst Chicagoans, whom he found seemed to ruefully delight in the city’s reputation for gangsters and political malpractice. “The contemplation of municipal corruption is always gratifying to Chicagoans,” he wrote. “They are helpless to do anything about it, but they like to know it is on a big scale.”

[chicagotribune2025-06-24-1] Christopher Borrelli (2025-06-24). "Was A.J. Liebling right about Chicago? Decades after the New Yorker's 'Second City,' time for a second reading". Chicago Tribune. Retrieved 2026-01-14. Arguably nothing in 100 years of the New Yorker landed on Chicago with more oomph than A.J. Liebling’s infamous 1952 three-part profile of the city. No, wait, strike “arguably” — that I’m writing this piece soon after my colleague Rick Kogan’s piece on how Liebling gave Chicago another nickname and inspired a certain comedy troupe, that alone suggests Liebling got under this city’s skin with a precision few can claim.

[chicagoreader1993-07-29-2] J. Weintraub (1993-07-29). "Why They Call It the Second City". Chicago Reader. Archived from the original on 2025-01-18. Retrieved 2026-01-14. In Chicago: The Second City Liebling saw such schizophrenic juxtapositions as being typical of Chicago boosters, who seemed to value quantity over quality and whose voices often rang as hollow as that of any pitchman defeated by the tawdriness of his goods.

[Wttw2022-12-15-3] "Revisiting the Biting Articles That Branded Chicago the "Second City"". WTTW Chicago. 2022-12-15. Archived from the original on 2025-03-16. Retrieved 2026-01-14. Liebling was familiar with this form of Chicago boosterism. In his infamous articles, which gave Chicago the “Second City” nickname, he noted a “first-or-nothing psychology” amongst Chicagoans, whom he found seemed to ruefully delight in the city’s reputation for gangsters and political malpractice. “The contemplation of municipal corruption is always gratifying to Chicagoans,” he wrote. “They are helpless to do anything about it, but they like to know it is on a big scale.”

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