Madonna’s 100 Greatest Songs (Critics’ Picks)

The history of pop music can essentially be divided into two eras: pre-Madonna and post-Madonna. Michael Jackson sold more albums and Prince was more prolific, but of the three singular musical icons born in 1958, Madonna is still the one who most set the template for what a pop star could and should be: bold, brilliant, ambitious, consistently innovative and constantly evolving.    

Madonna’s rise to galactic superpower status in the ’80s mirrored the rise of MTV as a cultural force, and hardly by coincidence: no figure since David Bowie married sound and vision so expertly. Before Madonna, artists could be considered daring if they reinvented themselves with each new album; she sped up the pace to where she was doing so practically with each music video, defining “iconic” so many times over she eventually had to make a song about it. Unlike many of her superstar predecessors and peers, there is no one true definitive Madonna sound or album — rather, there are a couple dozen definitive Madonna eras, which could last as long as four years or as short as, well, four minutes.   

Starting with her 1983 self-titled debut, the hits (and controversies) came quickly for the woman who boldly declared she wanted “to rule the world” during her North American network TV debut appearance on Dick Clark’s American Bandstand. Since then, she’s delivered on that promise, reigning as the undeniable Queen of Pop.

Her four decades of culture-shifting hits — including 12 Billboard Hot 100 No. 1s — will take center stage during her 2023 Celebration Tour. And there’s a lot to celebrate. For years, Madonna wasn’t ahead of the curve so much as consistently bending its angle with her gravity. She talked (and sang, and wrote, and performed) frankly about sex and desire at a time when doing so largely inspired mockery at best and condemnation at worst. She loudly championed her LGBT fanbase while many pop stars were still avoiding their existence altogether. She confronted misogyny, abuse and gender double standards inside and outside of the music industry for decades before there was any kind of nationwide #MeToo movement to support her.

While many of her peers struggled to adapt or openly railed against new trends in popular music, she successfully incorporated elements of house, trip-hop, techno, drum and bass, G-funk and Auto-Tune into her music at various points in her career, working with everyone from Nile Rodgers to Lenny Kravitz to Björk to Andrew Lloyd Webber to Pharrell to SOPHIE — scoring Billboard Hot 100 hits with all of them — without ever losing her center. She’s spent so much of her career dragging pop music into the future that it’s not surprising to see today’s pop stars continuing to call back to her, whether it’s Drake invoking her name as the ultimate superstar presence, or Ariana Grande casting her as the no-credit-needed voice of biblical female vengeance, or Rihanna simply using her entire career arc as the pace-setter for her own. 

But for all her innovation, iconicity and activism, what really endure are the songs. So many, many songs: well over 200 officially released tracks over the course of her career, a stunning percentage of which should remain familiar to even casual pop fans of her lifetime. Madonna scored her first Hot 100 top ten hit with “Borderline” in 1984, and her (to date) last with “Give Me All Your Luvin'” in 2012. In between, she’s amassed a total of 38 top ten hits — most of any artist in Billboard history, a record that stands tall even in this robust era of streaming-powered single-artist chart dominance. And the range of those hits is similarly unimpeachable, encompassing euphoric dance floor slayers, heartbreaking big ballads, bubblegum pop perfection, edgy electro-funk and the most vital radio-ready sounds in between.

We here at Billboard wanted to celebrate the living legend with a list of our 100 favorite tracks from her incredible career. See our picks below, and be sure to take one day out of life to celebrate your own favorites by the artist who remains the dictionary definition of pop stardom.