"Fool #1," Brenda Lee
Hot 100 Peak: 3 (1961)
This song is one of her impressive 12 top 10s that Lee enjoyed between 1959 and 1963. Clearly, she's beloved for more than just her holiday standard "Rockin' Around the Christmas Tree."
"Everybody Plays the Fool," the Main Ingredient
Hot 100 Peak: 3 (1972)
Here's 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 (misguided, ultimately) chance on love, sending it to No. 3 in 1972.
"Chain of Fools," Aretha Franklin
Hot 100 Peak: 2 (1968)
With 73, the Queen of Soul boasts the most Hot 100 hits by a female artist. Seventeen have reached the top 10, including this song, which 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).
"Poor Little Fool," Ricky Nelson
Hot 100 Peak: 1 (two weeks) (1958)
A stat that avid chart-watchers know well: the song holds the distinction of being the first Hot 100 No. 1 upon the chart's Aug. 4, 1958, launch. In the ensuing five decades, 1,022 more hits have since reigned.
"Fooled Around and Fell in Love," Elvin Bishop
Hot 100 Peak: 3 (1971)
The blues/rocker scored his biggest hit with this song about unintended deeper feelings eventually seeping in. Still a chart force, he's collected three top 10s on Billboard's Blues Albums survey since 2005.
"Foolish Beat," Debbie Gibson
Hot 100 Peak: 1 (one week) (1988)
Gibson's first No. 1 gave her unprecedented chart history: then 17, she became the youngest artist to write, produce and perform a Hot 100 No. 1. How did she celebrate the success? She graduated high school the next day.
"What a Fool Believes," the Doobie Brothers
Hot 100 Peak: 1 (one week) (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. (Or, maybe you know him best for his "South Park" contribution.)
"Everybody's Somebody's Fool," Connie Francis
Hot 100 Peak: 1 (two weeks) (1960)
Francis was an early '60s Hot 100 dominator, with this song marking her first of three No. 1s. Her 53 Hot 100 hits remain the fifth-most among women in the chart's entire history. Much more importantly, she's an esteemed humanitarian; her charity Haven from the Storm is set to conduct a telethon for Veterans on Memorial Day.
Hot 100 Peak: 1 (10 weeks) (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. (It's tied with the quite-different "You Light Up My Life" by Debby Boone in 1977.) Ashanti rung up a whopping 10 top 10s between 2002 and 2004. Having added acting roles to her resume, she's due to release her first album in five years in June.
"Foolish Games," Jewel
Hot 100 Peak: 2 (1997)
The piano ballad tops our tally, having become a Lilith Fair-era radio staple (backed with her previous hit "You Were Meant for Me"; the double-sided single spent 65 weeks on the Hot 100). Currently charting on Adult Contemporary with new single "Two Hearts Breaking," Jewel can be seen in the Lifetime movie "Ring of Fire," in which she stars as June Carter Cash. It premieres on May 27.