The definitive Madonna playlist

By the time Madonna released her third studio album, True Blue, in 1986, she was already among the most popular entertainers on the planet. That record only solidified the fact that all five singles released reached No. 1 on the Billboard Hot 100 in the United States or the Singles Chart in the United Kingdom. "La Isla Bonita" was the final single from the album, and topped the charts in the U.K., while peaking at No. 4 in America. The song represented co-writer Madonna's Latin music influence, something that was present well before she became an international superstar.

When it comes to greatest hits albums, Madonna's The Immaculate Collection (1990) really is as good as it gets. It features all her major hits (most of which are on this list), and this new track. Over the years, Madonna has never shied away from controversy, notably when it comes to her videos. The sultry, randy video for "Justify My Love" made waves, but the song is also unique for Madonna's hushed spoken-word performance. Co-written by Lenny Kravitz, "Justify My Love" reached No. 1 on the Billboard Hot 100.

Madonna's 12th, and most recent, No. 1 single in the Billboard Hot 100 in the United States, "Music" proved that she still had massive staying power at the dawn of the 2000s. "Music" picked up where Madonna's musical approach left off at the end of the 1990s when she was heavy into electronica, house, and even elements of funk. While it might not appeal to her 1980s' pure pop fans, "Music" proved Madonna's ability to grow as an artist, while also expanding her fan base to a new generation of listeners.

Madonna was never going to be just a musician. Her charisma and visual presence made her a natural for the big screen -- for better or worse. So, when she made a movie, she naturally contributed to said soundtrack. With 1987's Who's That Girl, it was a common tale where the soundtrack was actually better than the film. The song was Madonna's sixth No. 1 single on the Billboard Hot 100, and was nominated for both a Grammy Award and Golden Globe Award.

Madonna's fourth studio album Like A Prayer, from 1989, is not quite conceptual, but fair to describe ias autobiographical -- in a roundabout way. Madonna harkened back to her family life growing up on her most personal album in the arsenal, and on that sold more than 15 million copies. "Oh Father" was a top-20 hit, and deals with a young girl's relationship with her father following the death of her mother. Taken from Madonna's own life, the black-and-white video, directed by David Fincher, might be the most impactful and gripping of any visual performance she's given.

Madonna won the Grammy for Best Song Written for Visual Media for her contribution to the Austin Powers: The Spy Who Shagged Me soundtrack from 1999. "Beautiful Stranger" has that traditional Madonna "sound," but in a more subtle way, and fitting the British-themed, almost psychedelic -- or "shagadelic" -- vibe of the famed Mike Myers movie. Which tends to be the case when being part of a movie soundtrack. Though she won a Grammy for the tune, "Beautiful Stranger" barely cracked the top 20 in the Billboard Hot 100.

The 1990s were drawing to a close, but Madonna was still an international entertainment giant. She also continued to experiment with her music, which when you are among the most recognizable people on the planet, is expected. On 1998's Ray of Light, the dance vibe intensified. The title cut is a mix of pop, dance, electronica and house music. Thus, naturally, making it popular with club crowd and delivered Madonna another top-five single on the Hot 100.

Co-produced by the legendary Kenny "Babyface" Edmonds, the beautifully composed "Take a Bow" was Madonna's 11th single to top the Billboard Hot 100 chart. At the time, it broke Carole King's record for No. 1s by a female songwriter. The final track from Madonna's 1994 Bedtime Stories album, "Take a Bow" is a prime example of the artist infusing drama into her music -- notably the lyrics. Ever the entertainer and show-person, Madonna carried her dramatic appeal onto the screen with another popular music video.

As noted, Like a Prayer was a pretty deep album for a pop star. Yet, "Cherish" can be described as perhaps the record's most whimsical moments. A tune of love and loyalty, with a certain 50s' beachy, pop vibe, "Cherish" peaked at No. 2 on the Billboard Hot 100. Though Madonna was lauded for getting unabashedly personal on her fourth studio album, at the heart of things, she's still a pop star capable of producing plenty of feel-good moments.

As we know, Madonna is more than just a singer. Fashion trendsetter and movie star also grace her resume. She co-starred in Penny Marshall's beloved 1992 film A League of Their Own, about the World War II-era All-American Girls Professional Baseball League. Madonna also wrote this theme to the movie, which reached No. 1 on the Billboard Hot 100 in the United States -- giving her a record, at the time, 10th chart-topping single for a woman. It also earned a Golden Globe Award nomination for Best Original Song.

Another No. 1 Billboard Hot 100 result for Madonna. "Open Your Heart." was originally written, by prominent pop-rock composers Gardner Cole and Peter Rafelson, for Cyndi Lauper. It had more of a rock vibe back then, but ultimately landed in in the camp of Madonna, who reworked it into more of a dance number. Good thing, as "Open Your Heart" was another shining moment from True Blue, and the video exemplified how Madonna was a true entertainer who understood the value of visual performance within the confines of the entire process.

"True Blue" was a top-three hit for Madonna in the U.S., but it's also one of her more underrated songs. When compared to the other more celebrated gems from her third studio album. It's also one of Madonna's more undisputed pop tracks. Sure, it was popular with dance clubs and spawned all sorts of remixes and club versions, but there was an ode to those Motown pop hits of The Supremes and the like. The popular music video featured yet another new look for Madonna, sporting a short, platinum blonde hairstyle.

The world's introduction to Madonna came with her self-titled debut album from 1983. Produced by the legendary "Jellybean" Benitez, with her incorporation, as well, "Holiday" was part of her stellar rookie performance, and Madonna's first international hit. While it peaked at No. 16 on the Hot 100, "Holiday" continued the trend of Madonna's popularity with dance crowds and clubbers. It topped dance charts in both the U.S. and United Kingdom. 

The opening track from Madonna's aforementioned debut, "Lucky Star" followed a similar mold as "Holiday." Again working with "Jellybean" Benitez, Madonna furthered her musical reputation as a multi-versatile artist in terms of sound. Reaching pop, dance and even those fans still stuck in her disco past. "Lucky Star" made it to No. 4 on the Billboard Hot 100 and solidified Madonna as one of the best new artists of the early 1980s -- and one ready to rule the world.

As we know,  Madonna never had a problem pushing the envelope with her music, and the accompanying videos. From True Blue, "Papa Don't Preach," co-written with Brian Elliot, Madonna tackles the subject of teen pregnancy. Of course, that sparked discussion on both sides of the political, and the detailed music video, which featured Danny Aiello as the father of Madonna's character, only true more attention to the piece. The song went to No. 1 in more than 10 countries, in addition to the United States.

The first single from True Blue, "Live to Tell" was also part of the soundtrack for the 1986 film At Close Range, which featured Madonna's then-husband Sean Penn. Long regarded as one of Madonna's most significant moments as a songwriter, the deliberate, almost tortured-sounding tune, was her third No. 1 Billboard Hot 100 hit. In fact, there are plenty of critics who believe that "Live to Tell" just might be Madonna's best overall work.

Amongst all the ballads Madonna has recorded over the years, "Crazy for You" still seems to stand out above the rest. The love theme from 1985's Vision Quest, about a determined high school wrestler (Matthew Modine), who finds love in the process. "Crazy for You" was an FM radio staple as her career popularity continued to build. Madonna is even featured in the movie, performing the song and "Gambler," which is also included on the soundtrack. Back to "Crazy for You," which was another No. 1 hit on the Hot 100, and earned Madonna her first Grammy Award nomination -- for Best Female Pop Vocal Performance.

One of the many reasons Madonna attracted the masses was her overall confidence as a woman in the limelight. From the very beginning, she went toe-to-toe with the biggest male pop acts of the time and more than held her own when it came to global dominance and popularity. Like a Prayer's "Express Yourself" is a celebration of female empowerment. Her own personal anthem if you will. It was also her first collaboration with renowned producer Stephen Brey, "Express Yourself" reached No. 2 on the Hot 100.

The first cut from Madonna's signature album, Like a Virgin (1984), and the one offered another description of the pop superstar. By this point, Madonna was already well on her way to becoming a pop culture icon, and her second album proved her staying power as one of the world's biggest entertainers. An ode to materialism, and complete with its homage to Marilyn Monroe's "Diamonds Are a Girl's Best Friend" music video, "Material Girl" reached No. 2 on the Hot 100. 

There's a good chance pop fans forget that "Vogue" was one recorded for the soundtrack to 1990's I'm Breathless. the soundtrack album to Madonna's Dick Tracy film from 1990. A new decade meant an opportunity to produce another iconic moment in her career. One of Madonna's most recognizable tunes and music videos (once again under the direction of David Fincher, the fashion-fueled "Vogue" became a way of life. Spawning dance moves, fashion awareness and, of course, another No. 1 single for Madonna, who once again altered her image and set the pop culture world a blaze. Who can forget her over-the-top performance of "Vogue" at the 1990 MTV Video Music Awards?

As we've seen, Madonna is no stranger to lending her vocal talents to movie soundtracks that she's starred. Perhaps the most noteworthy moments of 1985's Desperately Seeking Susan is Madonna's supporting performance and this tune. Inspired by the dance-club vibe, "Into the Groove" kept the Madonna machine moving, topping dance charts in the U.S. (where it was initially released as a B-side to "Angel") and various international charts. It also added to her quickly building legacy that everybody, from just about any medium, wanted a piece. "Into the Groove" was eventually part of the Like a Virgin reissue.

"Dress You Up" was a top-10 hit for Madonna in the United States. Yet, when compared to some of her signature and internationally recognized tracks, it tends to get lost in the mix of pop greatness. That should not be the case. "Dress You Up" is not only one of the standout moments from Like a Virgin, but within Madonna's expansive catalog. Another gem produced by Nile Rodgers, who delivered the song's guitar solo that added an element of pop rock that spiced up Madonna's sound even more. 

Arguably Madonna's most ambitious work, when it came to her maturation as a songwriter, and vision for more bombast and drama in her music -- and, of course, music videos. When the title cut to their acclaimed fourth studio album was released, it was a true MTV moment. The video, about a young woman whose main adult male figure is God, was a mini-movie of sorts. It's imagery of burning crosses, the crucifixion, violence and suggestive unlawful carnal content, all amid a gospel background, only added to the intrigue and interest in Madonna's latest No. 1 hit.

The true gem of Madonna's debut record. "Borderline" was her first single to crack the top 10 on the Billboard Hot 100, was a massive MTV favorite (before her video debuts were appointment television) and displayed the magnitude and energy that were just a couple of reasons we couldn't stop talking about her as entertainment's next big thing. One of her more polished early tracks was perfectly placed at a time when female pop artists were coming into their own and proving their worth alongside their male counterparts.

Casual pop fans tend to forget that Madonna did not write "Like a Virgin" (credit that to Billy Steinberg and Tom Kelly), but she certainly made it her own. Notably, the somewhat controversial music video, which only added to the song's lasting legacy of girl's wanting to be her and guys aiming to be with her. Then again, shouldn't that be the point when garnering a mainstream audience? "Like a Virgin" is arguably Madonna's most recognized song, and her first to top the Billboard Hot 100.