30

"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.

29

"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.

28

"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." "You'll See's" music video became Madonna's first sequel clip -- as it followed the story set in motion in dramatic "Take a Bow" short.

27

"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. "Borderline's" 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."

26

"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."

25

"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.

24

"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.

23

"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.

22

"This Used To Be My Playground"

Hot 100 Peak Position: 1 Peak Year: 1992

Written for the film "A League of the Their Own," which co-starred Madonna, this delicate ballad become her 10th No. 1 single in the summer of 1992. It barely squeaked into the top slot, as it spent a solitary 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.

21

"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, "Angel's" 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.

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