Madonna's 40 Biggest Billboard Hits

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).

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.

After the madness of the boy toy era of Madonna's career (1983-1985), 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 easily reached No. 1 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 re-inventions.

"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).

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 upcoming Blond Ambition Tour.) The next day, "Like a Prayer's" 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," like so many of Madonna's singles, spawned a music video that garnered more attention than perhaps the song itself. The clip for "Justify My Love" 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.

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" is one of two No. 1 singles that she's yet to sing on tour -- the other is "This Used to Be My Playground."

Perhaps the ultimate slow-dance song, "Crazy For You" proved to be so popular upon its release, it bumped "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.

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.

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.

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