This weekend marked the 30th anniversary of Madonna’s first hit song, “Holiday.” The joyful tune turned Madonna into the still-reigning queen of pop, so I had to (just had to) collect my picks for the thirty subsequent singles that best define her career. I'm not saying they’re her best songs, per se. I'm not sure it's how I would rank my personal favorites. Even some memorable hits just couldn’t fit on the list. (Apologies to “Borderline” and “La Isla Bonita.”) But they are, if you ask me, the tunes that best encapsulate everything about her. They're the "most Madonna." Take some time to celebrate (just one day out of life) a legendary career.
30. Secret (1994)
Madonna has released over 70 singles in her career, and holds a record for the most top ten hits by any artist. With a catalogue that big, it’s easy to forget plenty of gems. Its slinky R&B groove made “Secret” something special, even if it’s not remembered for an accompanying scandal or bawdy “moment.” We like to talk about her ability to produce controversy and headlines, but at the end of the day, here’s what Madonna makes best: pop music.