10. Santana and Rob Thomas, 'Smooth'
Before Carlos Santana released "Smooth" in the summer of 1999 it was hard to imagine any scenario where he'd score a massive hit single. That was the year of Britney Spears, N'Sync and Ricky Martin – and Santana was a Woodstock veteran who hadn't been in the top 10 of the Hot 100 since "Black Magic Woman" almost 30 years earlier. But Clive Davis had the bright idea of pairing the guitar legend with younger pop stars for the LP Supernatural. The first single from the album was written by Matchbox Twenty frontman Rob Thomas, though the original idea was to have George Michael sing it. Santana liked Thomas' version so much that he decided to let him sing it on the album. The song shot to Number One, won a slew of Grammys and made Santana a household name again. It was one of the biggest comebacks in rock history, rivaled perhaps only by Meatloaf six years earlier.