The sketch is notable as a media portrayal of the Inland North dialect of American English that predominates in Chicago, most famously through the distinctive pronunciation of the phrase "Da Bears" (IPA: [ˈd̪ʌː ˌbeɻs]).
Shortly after Robert Smigel moved from New York to Chicago in 1983 to start his career in comedy, he made his first visit to Wrigley Field to see the Cubs play.
He noticed a prevalence of large men who wore walrus mustaches and aviator sunglasses, a look similar to Mike Ditka, who had been hired to coach the city's NFL team, the Chicago Bears, the year before.
The Cubs and the White Sox both made the playoffs for the first time in decades, the National Basketball Association's Bulls drafted Michael Jordan and in 1985 the Bears capped a 15–1 regular season with victory in Super Bowl XX.
[2] At that time, played by Smigel, Odenkirk and Dave Reynolds (with an occasional appearance by Conan O'Brien as one of the fan's sons), they were simply sitting on lawn chairs and drinking beer, but making the wild imaginative leaps by which they could assume the Bears would handily win another Super Bowl.
The sketch drew considerable laughter, but when it came time to stage the show in Los Angeles, Smigel cut it, believing audiences there would not understand it.
Mantegna liked it, and the writers finally came up with a setting, parodying The Sports Writers on TV, a long-running Chicago-area radio show that had been adapted for television by local UHF station WFLD-TV in 1985, featuring three veteran local sportswriters, including Bill Gleason, known for his thick Chicago accent, and Rick Telander, a relative newcomer, sitting around a table and discussing Chicago sports.
[1] Kevin Nealon also made a brief appearance as oddsmaker Danny Sheridan in the first sketch—he is promptly sent away by Bill after giving the Superfans an honest assessment of the prospect of Mike Ditka single-handedly defeating the Giants.
The characters were typically shown in Mike Ditka's sports bar, drinking large amounts of beer, smoking, and gorging themselves on ribs, Polish sausage, and similar foods.
One episode featured a Jeopardy!-like game show preempting the Bearless, and therefore unimportant, Super Bowl, starring Bob Swerski as host and the other Superfans as contestants.
The correct answer was revealed to be that such a match-up would tear the fabric of the space-time continuum and destroy the planet, meaning the United Nations would have to step in prior to the match to prevent the destruction.
The final sketch (actually a taped segment narrated by Bill Kurtis, ostensibly a TV documentary piece) featuring the original Superfans was on October 25, 1997, in an episode hosted by Farley.