16. "This Used to Be My Playground" (1992)
Madonna's tenth single to reach number one, this ballad was featured in the movie A League of Their Own. Madonna's performance in the movie was also well received by critics. The song wasn't included on the soundtrack, but it appeared on Madonna's ballad compilation, Something to Remember, released in 1995.
17. "Take a Bow" (1994)
Following the release of her controversial, best-selling book Sex (1992), Madonna experienced sagging chart positions. But "Take a Bow" changed all that. This farewell-to-love tune was a record breaker for Madonna, spending seven weeks at number one on U.S. charts.