Carlos Santana's Smooth Almost Featured A Completely Different Singer

Legendary rock guitarist Carlos Santana can, according to some interpretations, be said to have had two careers. His first was in the 1960s and 1970s, during which the Mexican-born American musician played at Woodstock, according to Britannica, and went on to become a staple of the classic rock of the era. This phase of Carlos' career produced such hits as "Black Magic Woman" and "Samba Pa Ti," among others.

Santana's second career, in a manner of speaking, began in 1999 with the release of the album "Supernatural." As Rolling Stone explains, at the time his career was stalling, but thanks in part to his collaboration with Rob Thomas, at the time one of the biggest stars in rock, the album went on to win multiple awards as well as re-energize the guitarist's lagging career.

One of the biggest tracks from that album, if not the biggest, was "Smooth," on which Thomas himself performed the lead vocals. The song remains one of the biggest hits of the era — and it almost featured not the Matchbox Twenty singer who made it famous, but another musician who, at the same time, was also years past his career-high points.

Carlos Santana's music was, is, and always has been a bit niche. His guitar-forward rock, sprinkled with Latin rhythms, may have been just what the 1960s and 1970s needed, but by 1999, thirty years had passed since Woodstock, and Santana was largely forgotten. His output in the 1990s had consisted of commercial failures, and by the end of the decade, according to the L.A. Times, he was without a record label. However, record executive Clive Davis saw Santana perform live and believed there was still commercial potential in Santana's music. Davis and Santana decided to put out another album — "Supernatural" — which would feature collaborations with some of the popular musical artists of the day, as Carlos at the time didn't sing on his records, according to the Las Vegas Review-Journal.

Just how big of a success "Supernatural" was won't be rehashed here, save to say that it sold millions, produced multiple hits, and won multiple awards, to say nothing of injecting new life into Santana's career. And, perhaps the biggest hit from that album was "Smooth," which features Santana "singing" in the sense that he makes his guitar do the singing for him, but in which Rob Thomas does the actual vocals. And Thomas himself admits that, when he wrote the song, he didn't consider himself the man for the job.

Rob Thomas wrote "Smooth" with Itaal Shur, and as he wrote for Billboard, when he was putting words to paper, he thought at the time that it would be the first and only song he wrote that he himself didn't sing. "When we finished the song, the conversation came around to who should sing it. I don't believe I was even in the running," he said.

In fact, when he wrote the song and recorded a demo track, he didn't even know who would wind up singing it. But, after discussion with Davis, they landed on George Michael. "It was George I had in my head when I recorded the vocals in the first place. If you listen to the melody and the cadence, it's an attempt to emulate his style in so many ways," he said.

Whether or not George wanted to record the vocals is not clear. What is clear, however, is that the record company wasn't feeling it. According to Smooth Radio, they wanted Thomas himself to record the track. The rest, as they say, is history.