Like a Virgin (1984)
One of the most defining songs of Madonna's career, "Like a Virgin" established the artist as a risk taker and gave us the first taste of her fearless exploration into her sexuality. Her MTV performance of the song — adorned in a wedding dress and writhing on the floor — is considered one of the most iconic in the award show's history.
Material Girl (1984)
Madonna's "Material Girl" was the quintessential 80s anthem of excess — conjuring images of both wealth and an array of accoutrements, the latter making the star a fashion icon with her famous layers of netted tops and bangles. Commenting on her hits "Like a Virgin" and "Material Girl," Madonna once said: "I liked them both because they were ironic and provocative at the same time but also unlike me. I am not a materialistic person, and I certainly wasn't a virgin, and, by the way, how can you be like a virgin? I liked the play on words, I thought they were clever. They're so geeky, they're cool."
Like a Prayer (1989)
"Like a Prayer" revealed that no sensitive subject was off limits to Madonna — not even religion or the Catholic Church. The accompanying music video proved just that with its burning crosses, depictions of stigmata and Madonna kissing a black saint. The video was so controversial, the Pope issued a statement condemning it. Conservative groups also joined in on attacking the song by boycotting Pepsi which used the song in its commercial.
Live to Tell (1986)
"Live to Tell" represented another defining moment in Madonna's life: she was madly in love with actor Sean Penn, whom she married in 1985. The song was featured in Penn's film At Close Range, which also starred Christopher Walken. Unfortunately, for Madge, her roller coaster relationship with Penn would end in divorce in 1989, although she'd later admit in her doc Truth or Dare that he was the love of her life. In later years, the ex-couple would become fond friends.
Express Yourself (1989)
The embodiment of power and independence, Madonna solidified her stature and urged all women to find their own with the female-empowering anthem "Express Yourself." The hit song was a celebration of women to express their feelings and "never go for second best." The industrial Metropolis-inspired music video was directed by David Fincher and its $5-million dollar budget was the most expensive of its kind up until that point.
Another one of her all-time hits, Madonna struck a pose with "Vogue," a song that celebrated escapism and gave a nod to the 1970s disco era. (Vogueing was introduced to Madonna at the Sound Factory in New York City.) The black-and-white music video was yet again the brainchild of David Fincher, who was still riding high on his 1920s-1930s retro kick.
Justify My Love (1990)
Let's talk about sex. Always running into controversy, Madonna's erotic hit, which was co-written by Lenny Kravitz, made waves when its music video depicted sadomasochism and bisexuality. The video was subsequently banned from MTV and other networks, to Madonna's dismay. "Why is it that people are willing to go and watch a movie about someone getting blown to bits for no reason at all, and nobody wants to see two girls kissing and two men snuggling?" she stated. Regardless of the ban, the song became a bestseller when it was released on VHS. Madonna also followed it up with a coffee table book simply entitled Sex in 1992.
Don't Cry For Me Argentina (1996)
Madonna's cover of the 1976 song, which was adopted in the 1978 musical Evita, was yet another milestone for the blonde bombshell. Madonna starred in the 1996 film adaptation in the title role as Argentine leader Eva Perón, opposite Antonio Banderas, and was arguably her most serious acting project. That same year the film came out, Madonna had also become a mother for the first time, giving birth to her daughter Lourdes.
Ray of Light (1998)
The title track to her seventh studio album marked Madonna's spiritual awakening. Incorporating electronic sounds, the club favorite gave form to the hippy dippy side of Madonna who began studying Kabbalah the year before.
Me Against the Music (2003)
Some fans winced at the elder pop icon frolicking about with her much younger sex pot successor Britney, but for Madonna, it was the beginning of her "I'm still here and still got it" tour. That same year, the blonde duo, along with an obscenely tan Christina Aguilera, performed at the MTV Music Awards and debuted that infamously sensual kiss, which didn't make Britney's ex Justin Timberlake all too happy. Cry us a river, JT...
Hung Up (2005)
The lead single off her tenth studio album, Madonna's "Hung Up" was an ode to 80s dance pop and resurrected the singer's popularity, which had waned with the release of her 2003 album American Life. The lead single soared to the top 10 of the Billboard Hot 100 and became the top dance song of the decade, as well as one of the hottest-selling singles of all time.
4 Minutes (2008)
Apparently, Justin had no hard feelings when Madonna kissed Britney at the 2003 MTV Music Awards. Collaborating with the Material Girl, JT offered his vocals on the Timbaland-produced track, which was co-written by Madonna. After a trip to Africa and seeing the humanitarian crisis around her, Madonna wrote the dance song, which carried the message of saving the environment. With over three million downloads, "4 Minutes," has become her most successful digital single to date.
B*tch I'm Madonna (2015)
Off of her album Rebel Heart, Madonna exuded celebratory defiance with her track "B*tch I'm Madonna." With its unusual arrangement, the EDM Diplo-produced song received mixed reviews from critics but, alas, shot to the top of the dance charts. Despite naysayers saying the 50-something-year-old was acting out of desperation, "B*tch I'm Madonna" was Madonna's way of saying she's still having fun because she's... her. That same year, she reiterated this message with her headline-grabbing kissing incident with Drake, who wasn't too keen on the singer's choice of lip gloss. Oh well, as long as Madonna's having a good time — that's her point, right?