Madonna Sings “This Used To Be My Playground” Live For The First Time Ever During Chicago Tour Stop

Posted February 4, 2024 by with 1 comment

If you’re a fan who’s familiar with her biggest hits that she’s performed live, this is, like, major. During a Chicago stop on her Celebration tour this week, Madonna sang a verse from her #1 1992 song “This Used To Be My Playground,” as you’ll hear in the video below. “Playground” had been the only one of her 12 #1 records that she never performed live a single time, until Friday night. It’s brief, but it’s a cute and historic moment for mega fans (she follows it with an acoustic version of “Express Yourself”):

“Playground” was of course written for Penny Marshall’s A League Of Their Own (which, other than Evita, is the movie with Madonna’s best work as an actress), and here’s a clip:

And the full track:

Background on chart performance for “This Used To Be My Playground” via Wikipedia:

In the United States, “This Used to Be My Playground” debuted on the Billboard Hot 100 chart at number 35, for the week of July 4, 1992. The debut was aided by just airplay points which enabled it to enter the Hot 100 Airplay chart at number 14. The song received immediate heavy rotation in US radio stations like Hot 97 in New York and Wild 107 in San Francisco. One week later, the song jumped to number 17 on the Hot 100, having had the largest sales and airplay gain of any record on the chart. On August 8, 1992, the song reached the top of the chart for one week, becoming Madonna’s tenth number one single, breaking her tie with Whitney Houston as the female artist with the most number one singles at that time. The song replaced “Baby Got Back” by Sir Mix-a-Lot although it was number three on the Hot Singles Sales and Hot 100 Airplay charts. According to Michael Ellis from Billboard, the song edged out “Baby Got Back” by a small margin of chart points. The song spent a total of 20 weeks on the chart and ranked at number 21 on the Hot 100 year end chart for 1992