The grandson of Daniel Boone, Albert Gallatin Boone , operated a grocery there for a time. While some people believe that for a time, a tunnel running south connecting to a stable was part of the Underground Railroad helping slaves escape to the North and that the tunnel still exists, running under the street to the stable, which is now also a drinking establishment called the Dark Horse Tavern, Kyle Kelly (one of the Kelly brothers who own the establishment) himself says, "There are many tales of our old building and this is one of the more common ones. I do not believe that there ever was a tunnel from Kelly's to any neighbor, but there certainly could have been. Our basement is 'interesting' and may cause someone to believe it was a former tunnel because the basement under the front part of the building resembles a tunnel."
Sometime around 1900, the Wiedenmann family operated a grocery there, which catered to Kansas City's elite. With the repeal of Prohibition, Phil Taggart rented the building and opened a saloon named the Wrestlers Inn. A few years later, Randal Kelly, born in County Clare, Ireland, became a bartender. He soon became a partner. The bar became a popular attraction, particularly during Saint Patrick's Day, and continues to be a well loved destination.
In 1996, Kansas City native Eddie Griffin used Kelly's as the inspiration for the setting of his sitcom Malcolm & Eddie, starring himself and Malcolm-Jamal Warner.