20

"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 where she shared 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."

19

"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 (1994). The strummy, hip-hop-light 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."

18

"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.

17

"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."

16

"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 one of her concert tours: 1987's Who's That Girl trek.

15

"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.

14

"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.) "Causing a Commotion" also ranks as Madonna's biggest Hot 100 hit (on this top 40 recap) without an official music video.

13

"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."

12

"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).

11

"Who's That Girl"

Hot 100 Peak Position: 1 Peak Year: 1987

We're entering rare 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.

NEXT PAGE: 10-11

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