Since arriving on the Hot 100 the week of Oct. 29, 1983, with "Holiday," she has earned a total of 57 chart hits, including a record 38 top 10s. Yes, you read that right: Madonna has more top 10 hits than any other artist in the history of the chart (and incidentally, Madonna was born the exact same month as the Hot 100). The Beatles are in second place, with 34 top 10s.
The ranking is based on actual performance on the weekly Billboard Hot 100 chart. 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 Position: 14 Peak Year: 1993
"Rain," the fourth single from 1992's Erotica album, comes in at No. 40 on Madonna's all-time biggest hits list. The commercial release of the maxi-single (and 12" vinyl) was bolstered by the previously unreleased track "Up Down Suite" as well as a jazzy/hip-hip remix of the Erotica album cut "Waiting" (featuring Everlast).
Hot 100 Peak Position: 20 Peak Year: 1990
Accompanied by a stunning black and white music video, the haunting ballad "Oh Father" was the fourth single from the Like a Prayer album. At the time, "Oh Father" had the unfortunate honor of ending Madonna's string of 17 consecutive top 10 hits. "Oh Father" stalled out at No. 20 while all 17 Madonna singles from "Borderline" (1984) through "Cherish" (1989) had reached the top 10.
"Don't Cry For Me Argentina" (From "Evita")
Hot 100 Peak Position: 8 Peak Year: 1997
"Don't Cry For Me Argentina" took an unconventional route to the top 10 on the Billboard Hot 100. Recorded as the sweeping centerpiece to the movie Evita, the song wasn't necessarily a made-for-radio hit single. However, uptempo dance mixes of the song were produced (which included new vocals from Madonna) and promoted to radio stations. The so-called "Miami Mix" (by producers Pablo Flores and Javier Garza) soon became a smash on the radio and led to a commercial release as a maxi-single and 12" vinyl. Pent-up demand for the remixes engineered a No. 17 debut on the Hot 100 for the single on Feb. 22, 1997. The following week it sailed to its No. 8 peak.
Hot 100 Peak Position: 16 Peak Year: 1984
Madonna's first Billboard Hot 100 hit (though not her first single), debuted at No. 88 on Oct. 29, 1983 - and the chart hasn't been the same ever since. The cut would eventually rise to No. 16 on Jan. 18, 1984 and was the first of three top 20 singles from Madonna's self-titled debut album. "Holiday" is also the third and final non-top-10 hit (with Nos. 37, 39 and 40) on this round-up of Madonna's biggest singles. Every other tune on this tally reached the top 10.
Hot 100 Peak Position: 10 Peak Year: 1990
In 1990, Madonna could have released pretty much anything and it would have been a hit single. Take for example this goofy (but catchy!) ditty about having a "good spanky." It reached No. 10 on July 28 of that year, as Madonna's massive Blond Ambition Tour was winding its way around the globe. "Hanky Panky" was the second, and final, single from the I'm Breathless album (a sort of companion set to the Dick Tracy film, in which she co-starred). The first Breathless release was "Vogue" - but more on that single in a little bit.
Hot 100 Peak Position: 9 Peak Year: 1991
"Rescue Me" was one of two new songs recorded for Madonna's first greatest hits album, 1990's The Immaculate Collection. When it debuted at No. 15 on the March 2, 1991 Hot 100 chart, it marked the highest-ever bow for a single by a woman. Further, it was - at the time - one of only four titles to debut in the top 20. The song had been an airplay hit for a full three months before it finally arrived on the Hot 100, as the single had been held back from commercial release. As "Rescue Me's" release was delayed until it had reached its peak of popularity on the radio, it had an artificially short run - eight weeks - on the Hot 100.
Hot 100 Peak Position: 7 Peak Year: 2005
The lead single from 2005's Confessions on a Dance Floor boogied its way to No. 7 on the Hot 100 in 2005 and was the first of two chart hits from her discofied album. (A second hit, "Sorry," reached No. 58.) "Hung Up" featured a galloping sample from ABBA's "Gimme! Gimme! Gimme! (A Man After Midnight)" while its video had Madonna channeling Saturday Night Fever whilst clubbing in London.
"Die Another Day"
Hot 100 Peak Position: 8 Peak Year: 2002
The title track from the James Bond film, released in 2002, became the first Bond tune to reach the top 10 on the Hot 100 since Duran Duran's A View to a Kill hit No. 1 in 1985. Further, "Die Another Day" was the first official Bond theme song to even chart on the tally since "A View to a Kill." The electro-hued single would go on to appear on Madonna's 2003 album, American Life.
"Ray Of Light"
Hot 100 Peak Position: 5 Peak Year: 1998
"Ray Of Light" continues to hold the record for Madonna's highest-debuting single ever, as it started at No. 5 on the Hot 100 chart dated July 11, 1998. The single was the title track (and second single) from Madonna's 1998 album, and went on to win a Grammy Award for best dance recording. Its corresponding music video, directed by Jonas Akerlund, also won a Grammy for best short form music video, and earned five MTV Video Music Awards (including Video of the Year).
Hot 100 Peak Position: 3 Peak Year: 1992
The dark and sexy single - the lead-off track from her 1992 album of the same name - launched with a bang at No. 13 on the Hot 100 dated Oct. 17, 1992. It zoomed to its peak of No. 3 the following week, kept out of the top two slots by Boyz II Men's "End of the Road" (No. 1) and Patty Smyth's "Sometimes Love Just Ain't Enough" (No. 2).