Madonna Surprises Fans In Chicago, Performs “This Used to Be My Playground” Live For The First Time

Madonna's “The Celebration Tour” recent stop in Chicago became a historic moment for fans as the iconic pop artist performed her 1992 No. 1 Billboard Hot 100 hit, "This Used to Be My Playground," live for the first time. The song, featured in the film A League of Their Own, had never been part of her live performances until the Chicago concert on February 2.

Addressing the audience at The United Center, Madonna fondly reminisced about filming the movie and learning to play baseball in the city. She shared her initial struggles and how she improved over months of practice. The singer, who co-starred in A League of Their Own as "All the Way" Mae Mordabito, engaged the crowd in a trip down memory lane, singing a few lines of the iconic song a cappella, with the audience joining in.

Madonna expressed surprise at the audience's familiarity with the track, jokingly stating, "I thought only 10 of you would know it. Turns out 20 of you knew it. I’m just kidding." She also shared her fond memories of the city, and its role in her learning baseball and filming the movie.

"This Used to Be My Playground" had previously been the only one of Madonna's 12 No. 1 Hot 100 hits that she had never performed live. The song, written by Madonna and Shep Pettibone, not only topped the Hot 100 but also reached No. 2 on the Radio Songs chart and No. 4 on the Adult Contemporary airplay chart. It received a Golden Globe Award nomination for Best Original Song and, in 2023, ranked as Madonna’s 19th-biggest song of all time on the Hot 100 chart.