Madonna Performs ‘This Used to Be My Playground’ Live for the First Time at Chicago Concert

Until last night, the A League of Their Own ballad was the only one of Madonna’s 12 Billboard Hot 100 No. 1s that she had not performed live.

Madonna performs during The Celebration Tour at The O2 Arena on Oct. 15, 2023 in London.

Kevin Mazur/WireImage for Live Nation

Fans attending Madonna’s The Celebration Tour stop in Chicago Friday night (Feb. 2) got to hear something the Queen of Pop has never done before: perform her 1992 No. 1 Billboard Hot 100 hit “This Used to Be My Playground” live. (Well, a bit of it, at least.)

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The song was written by Madonna and Shep Pettibone for the 1992 film A League of Their Own. Madonna co-starred in the baseball comedy-drama as “All the Way” Mae Mordabito, and the song played over the film’s end credits. Until last night, it was the only one of her 12 No. 1 Hot 100 hits that she had never performed live.

During the concert at The United Center, Madonna reminisced about filming the movie, which was a fictionalized story about the real-life All-American Girls Professional Baseball League.

“I hope that you guys remember,” she told the audience, “I made a film called A League of Their Own, and I had to learn how to play baseball in this city. I was here for months! And, um, I kinda sucked in the beginning, but I got good. I got good at it. All the Way Mae, that’s right. Remember her? I learned how to play baseball in this goddamn city! And do you remember the song? While we’re taking a trip down memory lane in my retrospective [show].”

She then sang a few lines, a cappella, of the beginning of “This Used to Be My Playground,” with the crowd’s help, telling the audience, “Aww, bless you,” after they joined her. She then joked, “I thought only 10 of you would know it. Turns out 20 of you knew it. I’m just kidding.”

“I have very fond memories of this city, I’m just saying,” she said.

In addition to topping the Hot 100 for one week in 1992, “Playground” reached No. 2 on the Radio Songs chart and No. 4 on the Adult Contemporary airplay chart. It would also go on to score a Golden Globe Award nomination for best original song. In 2023, it ranked as Madonna’s 19th-biggest song of all time on the Hot 100 chart.

Fun fact: In 2019, Billboard asked Madonna to consider performing three songs on her then-upcoming Madame X Tour — her three Hot 100 top 10 hits that she, at that point, had never performed live before. They were “This Used to Be My Playground,” “I’ll Remember” and “Rescue Me.” During preparations for the Madame X Tour, she rehearsed “Rescue Me,” but ultimately included it in the show as a pre-recorded spoken word interlude while she was offstage.

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