The.best.singles.of.all.time.60s.70s.80s.90s.no1s.1999 May 2026

Next: . The 1990s: “Smells Like Teen Spirit” – Nirvana

The song ended. He punched . The 1970s: “American Pie” – Don McLean The.best.singles.of.all.time.60s.70s.80s.90s.no1s.1999

He slid a quarter into the Wurlitzer. The first button glowed: . The 1960s: “(I Can’t Get No) Satisfaction” – The Rolling Stones The 1970s: “American Pie” – Don McLean He

The song faded. The diner was silent.

The clock read 11:58 PM. Leo had one song left. The diner was silent

Then he turned out the lights.

December 31, 1999. Billboard’s final #1 of the millennium. A song that mashed up Carlos Santana—a relic from Woodstock, Leo’s lost youth—with a new voice from Matchbox Twenty. It was a bridge. Old and new. Spanish guitar and rock radio. The world was about to click over to 2000, terrified of computer crashes and the unknown. But Leo just swayed. “Smooth” was velvet and fire. It was the last perfect single of a century that had given him love, loss, war, peace, and a jukebox full of memories.