A wall illustrated in 1976 by several cartoonists, including Bill Gallo, Stan Lee, Mort Walker, Al Jaffee, Sergio Aragonés, and Dik Browne, is still on display at the bar's final location.
The bar was founded in 1929 as a speakeasy on Third Avenue by brothers Tim and Joe Costello, who had emigrated to the United States from Ireland.
The writer John McNulty is credited with creating a mythology around Costello's—which he called "this place on Third Avenue"—through a series of short stories published in The New Yorker in the 1940s.
[5] Tim and Joe were born and raised in Ferbane, Ireland, to James and Teresa (née Flynn), who owned a drapery shop.
[4] Tim was known as an affable, intellectual proprietor, who was knowledgeable about literature, opinionated about art, and often well-dressed in a Brooks Brothers suit.
The bar was frequented by diplomats, United Nations employees, and the cast and crew of the soap opera Guiding Light.
[20] Regarding the closure of Costello's, the wines and spirits journalist Robert Simonson observed: "How quickly the character drains from things in 21st-century New York.
"[21] Costello's was decorated with illustrations that were painted and drawn directly on the walls by several notable cartoonists, including James Thurber, Bill Gallo, Stan Lee, Mort Walker, Al Jaffee, Sergio Aragonés, and Dik Browne.
[24] The journalist Jacquin Sanders described the cartoons as black and white illustrations that were "full of large, angry women, small, cowed men and regretful dogs".
The New York Times journalist Murray Schumach wrote that he borrowed the keys to the bar and painted the cartoon in one day in the winter of 1935.
[23] Eventually, he struck a deal with Costello to close the bar and provide free food and drink for the approximately 40 cartoonists who contributed to the wall, including Stan Lee, Mort Walker, Al Jaffee, Sergio Aragonés, and Dik Browne.
[32] In 2009, the wines and spirits journalist Robert Simonson wrote that the 2005 illustrations "feel like wan attempts to recapture a more glorious artistic past", noting that each of the characters had been given dialogue advertising the Overlook.
John McNulty wrote about the discussions and happenings at the bar, which he called "this place on Third Avenue", in the 1940s in a series of short stories for The New Yorker.
[35] According to the journalist George Frazier in Esquire, "there were those New Yorker writers who considered it unthinkable to hand in their manuscripts to the magazine before getting [Tim Costello's] approval".