No Foolin’: The Biggest Billboard Hot 100 Hits With ‘Fool’ in Their Titles

Dating to the start of the Billboard Hot 100, and surely long before, music fans have been fools for songs about fools. (It seems to make sense, as who can’t relate to acting or feeling a bit foolish? And not just on April 1.)

The chart began with the edition dated Aug. 4, 1958. No. 1 on the first ranking? “Poor Little Fool,” by Ricky Nelson. Plus, at No. 58 was “Fool’s Paradise,” by The Crickets. Most recently, on the July 22, 2023-dated chart, Taylor Swift hit No. 40 with “Foolish One (Taylor’s Version) (From the Vault).”

With another April Fools’ Day upon us, and as we all remain on high alert not to get pranked (at least not too badly), fools for chart history can explore Billboard’s roundup of the 25 biggest songs with the word “fool” in their titles. From tracks by Nelson and Swift to those by Luther Vandross, George Michael, Elvis Presley, Diana Ross, Aretha Franklin and more, the songs below became beloved hits.

The Biggest Billboard Hot 100 Hits With ‘Fool’ in Their Titles recap is based on actual performance on the weekly Billboard Hot 100 chart, from its Aug. 4, 1958, inception through March 29, 2025. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. To ensure equitable representation of the biggest hits from each era, certain time frames were weighted to account for the difference between turnover rates from those years.