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.
Hot 100 peak: No. 12 / Sept. 16, 1978
The debut hit by the British singer-songwriter and guitarist also topped the Adult Contemporary chart for three weeks. In recent years, his 1988 carol “Driving Home for Christmas” has become a staple over the holidays on Billboard’s global surveys.
Hot 100 peak: No. 18 / Feb. 16, 1985
Journey rang up 13 top 20 hits with Perry as its frontman in 1979-96. As a soloist, he logged three, including this enduring ballad. (Fun fact: A Providence, R.I., radio DJ’s musical crush is Steve Perry. She married someone named Perry, but presumably not just because it would become her last name.)
Hot 100 peak: No. 13 / Feb. 14, 1987
The song served as the rockers’ debut hit. A year later, the group rose one notch higher for a career best with “Don’t Know What You Got (Till It’s Gone).”
Hot 100 peak: No. 9 / Feb. 22, 1964
Four years after hitting the top 10, the vocal group charted another “fool”-titled hit: “Be Young, Be Foolish, Be Happy.” In 1992, the latter made the Adult Contemporary chart as covered by British singer Sonia (who likewise is known for another song with “fool” in its name, “Only Fools [Never Fall in Love]”).
Hot 100 peak: No. 10 / June 5, 1976
The song became the 16th of the Stones’ 23 Hot 100 top 10s, earned between 1964 and 1989. Among duos/groups, only The Beatles boast more top 10s (35), with Chicago and The Supremes tied for third (20 each).
Hot 100 peak: No. 6 / Sept. 28, 1968
The Latin/jazz/bossa nova legend covered The Beatles for his second of three Hot 100 top 10s. Mendes, who passed in September 2024, released more than 50 albums, dating to his first in 1961.
Hot 100 peak: No. 10 / March 21, 1981
1970s/early ’80s chart royalty didn’t get much bigger than this. Streisand tallied five No. 1s in that period and, with his brothers in the Bee Gees, Gibb scored nine. Streisand and Gibb connected for two top 10 duets in 1981: this song and prior single “Guilty,” which reached No. 3.
Hot 100 peak: No. 9 / Nov. 2, 1991
The perfect holiday for the late R&B legend is probably Valentine’s Day, given his wealth of sultry love songs. This one fits for today, though! It became his second top 10 of 1991, following “Power of Love/Love Power.”
Hot 100 peak: No. 4 / May 25, 1963
The vocal group gave us Motown-era classics including their No. 1s “Will You Love Me Tomorrow” in 1961 and “Soldier Boy” in 1962. This song became their sixth and final top 10.
Hot 100 peak: No. 8 / Oct. 19, 1991
After notching his first Hot 100 top 10 in 1967 with “Tell It Like It Is,” Neville returned to the region in 1989 on his duet with Linda Ronstadt “Don’t Know Much.” “Everybody Plays the Fool” then became his third, and most recent, top 10.
Hot 100 peak: No. 8 / Sept. 17, 1988
Loggins was a soundtrack king in the ’80s, scoring hits from Caddyshack, Footloose, Top Gun and, in 1988, Caddyshack II. This song from that sequel became the most recent of his five career solo top 10s.
Hot 100 peak: No. 5 / Dec. 7, 1963
Then 17, Gore blasted in with the 1963 No. 1 “It’s My Party.” By the end of the year, she added two more No. 5 hits: “Judy’s Turn To Cry” and this song. Michael Gore, her brother, has enjoyed his own chart success, notably co-writing and producing Irene Cara’s 1980 No. 4 smash “Fame.”
Hot 100 peak: No. 5 / Nov. 26, 1988
For the follow-up to four No. 1s from his debut solo album, Faith, Michael took an adventurous turn, releasing this elegant ballad perhaps better suited to a piano bar than pop radio. The singer-songwriter’s popularity and the song’s hooks, however, helped spur another hit from Billboard’s top album of 1988.
Hot 100 peak: No. 7 / Nov. 1, 1997
The piano ballad was initially the B-side to Jewel’s No. 2-peaking “You Were Meant for Me.” Once it became promoted as a follow-up, it began showing on the Hot 100 as the double-sided single’s first listed title, in September 1997. It returned to the top 10, reaching No. 7 that November, and ruled the Adult Pop Airplay chart for five weeks.
Hot 100 peak: No. 2 / April 27, 1959
Shouldn’t any list of great songs include at least one by the King? This is one of Presley’s 81 top 40 hits since the Hot 100 began.
Hot 100 peak: No. 7 / Dec. 19, 1981
The song was introduced by Frankie Lymon & the Teenagers in 1956, two years prior to the Hot 100’s inception, and led two of Billboard’s R&B charts that year. Ross isn’t the only big-name act to cover it: so have the Beach Boys, Joni Mitchell and Frankie Valli.
Hot 100 peak: No. 3 / Nov. 13, 1961
The song became the eighth of the 12 top 10s that Lee earned in 1960-63. She returned to the top 10 over the 2018 holidays with “Rockin’ Around the Christmas Tree,” which danced merrily to No. 1 at last in December 2023, marking her third leader.
Hot 100 peak: No. 3 / Oct. 14, 1972
This classic is the only song on the list to appear twice. Before Aaron Neville took it to No. 8 in 1991 (see No. 16 above), this Harlem group introduced the tale of taking a chance (unrequited, ultimately) on love.
Hot 100 peak: No. 2 / Jan. 20, 1968
The song is one of the Queen of Soul’s 17 Hot 100 top 10s. It also won the Grammy Award for best female R&B vocal performance in 1969. Franklin monopolized the category with wins in each of its first eight years (1968-75).
Hot 100 peak: No. 1 (two weeks) / beginning Aug. 4, 1958
“How cool is that? The very first No. 1,” Gunnar Nelson, Ricky’s son and half of fellow chart-topping sibling duo Nelson, told Billboard in 2020. “What I love about the story of ‘Poor Little Fool’ is that that was a song that was never meant to be a hit, let alone the first Billboard [Hot 100] No. 1.” Click here for the backstory.
Hot 100 peak: No. 3 / May 22, 1976
The blues/rocker scored his biggest hit with this song about unintended deeper feelings eventually seeping in. Still a chart force, he has collected seven top 10s, including one No. 1, on Billboard’s Blues Albums survey since 2005.
Hot 100 peak: No. 1 (one week) / June 25, 1988
As Gibson was 17 years old when the ballad reigned, she became the youngest woman to have written, produced and performed a Hot 100 No. 1, a mark that still stands. “When I was writing it,” she recalled in 2013, “I was guessing what love would be like… and then also guessing what it would be like to lose love. Now that I’ve been through all that, I can sing the very simple lyrics and really fill it.”
Hot 100 peak: No. 1 (one week) / April 14, 1979
Few groups have mixed rock and soul as deftly, and memorably, as the Doobies, who sent 27 songs onto the Hot 100 in 1972-89. The latter style won out upon the addition of lead singer Michael McDonald in 1976. His solo career, meanwhile, includes three ’80s top 10s.
Hot 100 peak: No. 1 (two weeks) / beginning June 27, 1960
Coincidentally, the first Hot 100 No. 1s by both solo men and women contain “fool” in their titles. After Ricky Nelson inaugurated the chart with “Poor Little Fool,” Francis became the first solo woman to reign when “Everybody’s Somebody’s Fool” topped the June 27, 1960, survey. The song marked her first of three No. 1s (earned through 1962), the most among solo women during the ‘60s.
Hot 100 peak: No. 1 (10 weeks) / beginning April 20, 2002
The song shares the mark for the longest-reigning Hot 100 hit by a woman in her first chart visit as a lead artist (tied with Debby Boone’s “You Light Up My Life” in 1977). Ashanti went on to up her career total to 10 top 10s through 2004.
Last July, Ashanti gave birth to her first child, son Kareem Kenkaide Haynes, with Nelly. “We’re going to add some more,” she shared earlier this year. “Definitely a girl to balance it out. I’m outnumbered in the house right now. So, a girl would be great … I am feeling amazing, incredibly pleased, humbled. My life has completely changed for the better. I feel full, you know? My cup is full.”
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