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.
"Rain" 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).
"Oh Father" 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.
"Holiday" 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.
"Hanky Panky" 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.
"Rescue Me" 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.
"Hung Up" 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).
"Erotica" 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).
"Deeper And Deeper" Hot 100 Peak Position: 7 Peak Year: 1993
The Erotica album's swirling second single, "Deeper and Deeper," topped out at No. 7 on the Hot 100, spending 17 weeks on the list. Its retro music video is riddled with cameos, including her now manager Guy Oseary, Sire Records chief Seymour Stein, longtime friend and actress Debi Mazar and adult film director/DJ/drag diva Chi Chi LaRue.
"Keep It Together" Hot 100 Peak Position: 8 Peak Year: 1990
"Keep It Together" was the fifth commercial single from Madonna's 1989 Like a Prayer album and was initially planned to carry with it a previously unreleased b-side. The b-side in question? "Vogue." Luckily, that anthem would go on to have its own single release. Instead, "Keep It Together" set sail on its own - without a sexy b-side to spice up sales. However, "Keep It Together" was remixed to become slightly more radio-friendly. Its redux was reminiscent of the then-popular track "Back to Life" by Soul II Soul.
"You'll See" Hot 100 Peak Position: 6 Peak Year: 1995
Composed and produced with David Foster, "You'll See" was one of a handful of new tunes Madonna recorded for her 1995 ballads collection Something to Remember. The ballad, which showcased Madonna's newly-trained vocal abilities, would prepare audiences for her lead role in the following year's Evita. The "You'll See" music video became Madonna's first sequel clip - as it followed the story set in motion in the dramatic "Take a Bow" short.
"Borderline" Hot 100 Peak Position: 10 Peak Year: 1984
Madonna's first top 10 single was the first of a staggering 17 consecutive top 10s for the singer from 1984 through 1989. The "Borderline" music video was the first collaboration between Madonna and director Mary Lambert, who would go on to helm her clips "Like a Virgin," "Material Girl," "La Isla Bonita" and "Like a Prayer."
"Don't Tell Me" Hot 100 Peak Position: 4 Peak Year: 2001
"Don't Tell Me" was the second single from the Music album and was co-written by Madonna's brother-in-law, recording artist Joe Henry. He would later release his own version of the track, re-titled "Stop," on his 2001 album Scar.
"Frozen" Hot 100 Peak Position: 2 Peak Year: 1998
The lead single from the Ray Of Light album marked a sonic change in Madonna's career, thanks to its co-producer, William Orbit. The track was heavily influenced by electronic dance music and peaked at No. 2 on the Hot 100. It would have perhaps reached the top of the chart, had it not been for K-Ci & JoJo. The week that "Frozen" zoomed from No. 5 to No. 2, the R&B duo's "All My Life" raced up the chart from No. 15 to No. 1 - blocking Madonna from the penthouse.
"Lucky Star" Hot 100 Peak Position: 4 Peak Year: 1984
"Lucky Star" is the lone Hot 100 hit in Madonna's catalog that was composed entirely by the diva herself. The uptempo number riffs a bit on the old nursery rhyme "Star Light, Star Bright" and has endured as one of Madonna's most beloved dance tracks.
"Dress You Up" Hot 100 Peak Position: 5 Peak Year: 1985
"Dress You Up" is the first of four singles on this tally from Madonna's Like a Virgin album. The plucky dance track was produced by Chic's Nile Rodgers (as was the rest of the Virgin album) and was the final single released from the set.
"This Used To Be My Playground" Hot 100 Peak Position: 1 Peak Year: 1992
Written for the film A League of the Their Own, co-starring Madonna, this delicate ballad became her 10th No. 1 single in the summer of 1992. It spent a week at No. 1 - sandwiched between two monster hits. It followed a five-week No. 1 run by Sir Mix-a-Lot's "Baby Got Back" and immediately preceded a 13-week reign by Boyz II Men's "End of the Road." Curiously, Madonna has yet to perform "This Used to Be My Playground" live - either on tour or during a promotional appearance.
"Angel" Hot 100 Peak Position: 5 Peak Year: 1985
One of Madonna's many singles which she co-wrote with Stephen Bray, "Angel" reached No. 5 on the Hot 100 in 1985. Rather famously, the "Angel" 12" vinyl single contains one of the most famous b-sides in U.S. history: "Into the Groove." While "Into the Groove" received a proper release in other countries, in America, it was relegated to b-side status despite its enormous popularity both on the radio and on MTV.
"4 Minutes" Hot 100 Peak Position: 3 Peak Year: 2008
"4 Minutes" is notable in that it was only the second single release in the U.S. from Madonna on which she shares credit with another artist. Justin Timberlake and Timbaland joined forces with her on the track - a little under five years after Madonna had first paired with Timberlake's former flame, Britney Spears, for "Me Against the Music."
"Secret" Hot 100 Peak Position: 3 Peak Year: 1994
Co-produced and co-written with Dallas Austin, "Secret" was the first single from Madonna's R&B-hued Bedtime Stories album in 1994. The strummy, hip-hop-lite song reached No. 3 on the Billboard Hot 100 - stuck behind Boyz II Men's "I'll Make Love to You" (No. 1) and Sheryl Crow's "All I Wanna Do."
"La Isla Bonita" Hot 100 Peak Position: 4 Peak Year: 1987
The Spanish-flavored track seems to be a favorite of Madonna's, as it has been included on the setlists of many of her concert tours. She also performed it at the 2007 Live Earth benefit show in London. "La Isla Bonita" was the fifth and final single from her True Blue album, and the cut reached No. 4 on the Hot 100.
"Cherish" Hot 100 Peak Position: 2 Peak Year: 1989
The light, lovey-dovey pop song was a throwback to '60s girl groups and doo-wop music, with couplets like "Romeo and Juliet they never felt this way, I bet" and "You are my destiny, I can't let go, baby, can't you see." The song's companion video clip was the first directed by photographer Herb Ritts. He had previously shot Madonna's album covers for True Blue and Like a Prayer.
"True Blue" Hot 100 Peak Position: 3 Peak Year: 1986
"True Blue," the title track from Madonna's 1986 album, spent three weeks stuck at No. 3 on the Billboard Hot 100. All about "true love, oh baby," the single is an unabashed peppy love song. Perhaps an indication of Madonna's (lack of) fondness of the track - it has only been performed on two of her concert tours: 1987's Who's That Girl trek and the 2015-2016 Rebel Heart Tour.
"Express Yourself" Hot 100 Peak Position: 2 Peak Year: 1989
"Come on girls, do you believe in love?" Well, Madonna had something to say about it in 1989, when "Express Yourself" was released as the second single from the Like a Prayer album. The single's video was directed by a pre-super-stardom David Fincher and was the first of four video collaborations between the two artists.
"Causing A Commotion" Hot 100 Peak Position: 2 Peak Year: 1987
"Causing a Commotion" was the second single from Madonna's Who's That Girl soundtrack, peaking at No. 2 for three straight weeks. (It was prevented from reaching the top by Michael Jackson's "Bad," which jumped to No. 1 the same week "Commotion" hit No. 2 for the first time.) "Commotion" also ranks as Madonna's biggest Hot 100 hit (on this top 40 recap) without an official music video.
"I'll Remember" (From "With Honors") Hot 100 Peak Position: 2 Peak Year: 1994
"I'll Remember," from the film With Honors, is one of six Madonna singles that have peaked at No. 2 on the Billboard Hot 100. Madonna holds the record for the most No. 2 hits in Hot 100 history. This particular track was lodged in the runner-up position for four weeks, behind All-4-One's "I Swear."
"Material Girl" Hot 100 Peak Position: 2 Peak Year: 1985
"Material Girl" is one of those singles that some people might assume was a No. 1 hit for Madonna. However, it topped out at No. 2 on the Hot 100 tally in 1985. As the second hit from the Like a Virgin album, the song would also become a nickname for the diva herself (whether she liked it or not).
"Who's That Girl" Hot 100 Peak Position: 1 Peak Year: 1987
We're entering rarified air now, as every one of Madonna's top 11 hits of all time on the Hot 100 chart are all No. 1s. "Who's That Girl" was the title track of the Madonna film and doubled as the lead single from its companion soundtrack.
"Open Your Heart" Hot 100 Peak Position: 1 Peak Year: 1987
Madonna's third single from True Blue shot to No. 1 on the Hot 100 on Feb. 7, 1987, marking the singer's fifth chart-topper. Its video caused a stir as Madonna starred as an exotic dancer who becomes friends with a boy (played by dancer Felix Howard).
"Music" Hot 100 Peak Position: 1 (four weeks) Peak Year: 2000
Madonna's most recent Billboard Hot 100 No. 1 is "Music," which spent four weeks atop the tally in late 2000. The cut was the lead single of the Music album, which again teamed her with William Orbit (Ray of Light). The single itself, like a fair portion of the album, was co-written and co-produced by Madonna and Mirwais.
"Live To Tell" Hot 100 Peak Position: 1 Peak Year: 1986
After the madness of the boy toy era of Madonna's career (1983-85), she surprised many with "Live to Tell," the lead track from her 1986 album True Blue. The haunting ballad was written partially for the film At Close Range (which starred her her then-husband Sean Penn) and found the No. 1 target on the Hot 100. The song was accompanied by a music video that introduced a decidedly toned-down Madonna to the public - one of the diva's first major so-called reinventions.
"Papa Don't Preach" Hot 100 Peak Position: 1 (two weeks) Peak Year: 1986
"Papa Don't Preach" was one of the few songs that even Madonna's most conservative critics could find reason to champion. The song tells the story of a young woman who confesses to her father that she's become pregnant, however, she's opting to keep her baby (as opposed to giving it up).
"Like A Prayer" Hot 100 Peak Position: 1 (three weeks) Peak Year: 1989
Would anyone have thought that "Like a Prayer" - which caused so much controversy in 1989 upon its release - would ultimately end up being performed at the Super Bowl halftime show in 2012? Yeah, we didn't think so. The song premiered in a two-minute Pepsi commercial that aired during The Cosby Show on March 2, 1989. (Pepsi was set to sponsor Madonna's then-upcoming Blond Ambition Tour.) The next day, the "Like a Prayer" music video debuted ... you know, the one with the burning crosses, stigmata and so on? Yes, well, Pepsi high-tailed it away from Madonna and she - again - outraged the masses.
"Justify My Love" Hot 100 Peak Position: 1 (two weeks) Peak Year: 1991
"Justify My Love," like so many of Madonna's singles, spawned a music video that garnered more attention than perhaps the song itself. Its clip was so racy, MTV declined to air it entirely. Luckily for the buying public, Madonna opted to sell the video as the first-ever commercially-available video single.
"Take A Bow" Hot 100 Peak Position: 1 (seven weeks) Peak Year: 1995
It may surprise some, but "Take a Bow" spent more weeks at No. 1 than any other Madonna single. (However, on this list, it ultimately ranks at No. 4.) With a seven-week run atop the Hot 100, 1995's "Take a Bow" returned her to the top of the chart for the first time since 1992 ("This Used to Be My Playground"). Co-written and co-produced with Babyface, "Take a Bow" was surprisingly never performed in concert until 2016, during the Rebel Heart Tour.
"Crazy For You" Hot 100 Peak Position: 1 Peak Year: 1985
Perhaps the ultimate slow-dance song, "Crazy for You" proved to be so popular upon its release that it bumped the all-star charity single "We Are the World" by USA for Africa out of the No. 1 slot. Before "Crazy for You" had reached the top, though, it had sat in the No. 2 position for three straight weeks, biding its time until it could push "We Are the World" aside.
"Vogue" Hot 100 Peak Position: 1 (three weeks) Peak Year: 1990
Initially planned as the b-side of "Keep It Together," Madonna's tribute to the fierceness that is vogueing was thankfully released as a single on its own. The thumping dance number is as iconic as its glamorous black-and-white music video, which was directed by David Fincher.
"Like A Virgin" Hot 100 Peak Position: 1 (six weeks) Peak Year: 1984
It's somehow appropriate that Madonna's first No. 1, "Like a Virgin," tops our list of her 40 biggest Hot 100 hit singles. The title track and lead single from her 1984 album spent six weeks atop the chart and became one of the diva's signature songs. It was written by Billy Steinberg and Tom Kelly and produced by Nile Rodgers.