The Story Behind “Smooth” by Santana and the Superstar Rob Thomas Originally Wanted to Have Sing It

When Santana released their 1999 album Supernatural, the band had not had a Top-40 hit or a Gold or Platinum album in 17 years. The album broke that commercial slump in a big way, and in no small part thanks to its lead single “Smooth.” Supernatural was Diamond certified less than nine months after its release, and “Smooth” ranks as one of the most popular singles of all time.

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If you’ve ever wondered how Rob Thomas wound up singing on a Santana song, it turns out the Matchbox Twenty frontman took a circuitous route to performing on “Smooth.” If Thomas had his way, one of the biggest pop stars of the ‘80s and ‘90s would have sang lead on the hit instead. Here is how he became the voice behind one of the most recognizable songs in pop history.

The A&R Executive Behind the Hit

You could chalk the success of “Smooth” up to the combined star power of Santana and Thomas, but that partnership would have never happened if not for an Arista A&R executive named Pete Ganbarg. Carlos Santana’s long association with Columbia Records ended with his band’s 1990 album Spirits Dancing in the Flesh, and after making Milagro (1992) with Polydor Records, he went looking for a new label. Clive Davis, who signed Santana to Columbia, added Santana to the Arista roster and connected him with Ganbarg.

One of the people whom Ganbarg solicited for songs for Santana’s first album on Arista was the manager of Itaal Shur, the keyboardist for the jazz group Groove Collective. At the time his manager was contacted by Ganbarg, Shur’s best-known writing credit was for Maxwell’s Top-40 hit “Ascension (Don’t Ever Wonder).” Being a fan of Santana, Shur told Songfacts he was eager to write a song for their new album. He wrote a piece called “Room One Seven,” and the label loved the tune, but not the lyrics. Ganbarg asked Shur to collaborate with Thomas, who would rework the lyrics he had composed.

Regarding Ganbarg, who had been working on his teaching certificate at Wesleyan University prior to going into the music business, Shur said, “if it wasn’t for him, this song wouldn’t have come together, because he put me and Rob together. He said some really good comments about the lyrics—he was an English major and really picky about lyrics. It was a really good collaboration.”

Thomas Wrote “Smooth” for a Pop Superstar to Sing

Like Shur, Thomas was thrilled to have an opportunity to write for Santana. In a 2017 interview for Billboard, Thomas said it was the first song he ever wrote that he wasn’t going to perform himself. That’s right—Thomas had no intention of singing “Smooth” himself and wasn’t aware he would ever be considered for that role. Davis and other Arista executives looked to Thomas for input on who should sing the song, and the first vocalist he suggested was one of his musical heroes, George Michael. Thomas told Billboard, “In fact, 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.”

It was Thomas’ performance on a demo of “Smooth” that sold Santana on the idea of him performing on the record. According to Thomas in an interview for VH1, “Carlos said, ‘I like this guy. Does he sing? I believe it when he sings.’ Instead of it being about ‘Let’s get this guy who had sold however many records,’ it was about, ‘I like this guy’s voice, let’s have him do the song.’ I can’t imagine he would have any idea who the h–l [Matchbox Twenty] were.”

One of the Biggest Hits of All Time

Santana clearly had superb judgment in having Thomas sing the lead vocals on “Smooth.” The song became the group’s first No. 1 single, and it topped the Billboard Hot 100 for 12 weeks. On Billboard’s all-time ranking of Hot 100 songs, “Smooth” ranks third, trailing only The Weeknd’s “Blinding Lights” and Chubby Checker’s “The Twist.”

Even though “Smooth” is almost unparalleled in its success on the singles chart, it is actually not the most popular Santana song in the streaming world. Its 385 million streams on Spotify are 20 million shy of the total for another single from Supernatural, “Maria Maria” (featuring The Product G&B and Wyclef Jean). “Maria Maria” has also been the more popular of the two songs on YouTube, garnering more than 560 million views, as compared to the nearly 370 million views received by the official video for “Smooth.”

Santana never again approached the level of chart success attained by “Smooth.” That was to be expected—even The Beatles and Michael Jackson have placed no more than two singles on Billboard’s all-time Hot 100. Still, they came back in 2002 with the Double Platinum album Shaman and the Top-5 single “The Game of Love” (with Michelle Branch). Santana would also team up with Thomas for two more chart hits—a cover of Cream’s ”Sunshine of Your Love” in 2011 and “Move” in 2021 (also featuring American Authors). Those two successive singles further solidified the link between Santana and Thomas—one that would have never occurred if Thomas had succeeded in getting the vocalist for “Smooth” he wanted in the first place.

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Photo by Arturo Holmes/Getty Images

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