Twenty-seven years ago this week, on the Billboard Hot 100 dated October 23, 1999, a Latin rock groove with a pop singer on top climbed to No. 1 in America. The guitarist had been making records for three decades. The singer was a 27-year-old from a Florida rock band. Together, Santana and Rob Thomas had made “Smooth,” and it would not leave the top of the chart until the new millennium had begun.
In this On This Day feature, we look back at a song that started life with a different name, the record label comeback that made it possible, and the twelve straight weeks that turned “Smooth” into one of the biggest hits in Hot 100 history. The official video is waiting for you at the end of the article.
▶️ Want to see Rob Thomas and Carlos Santana heat up the street first? Scroll down. The official “Smooth” video is at the end of the article.
A Guitar Legend Without a Label
By the mid-1990s, Santana was already a legend. Mexican-born guitarist Carlos Santana had formed the band in San Francisco in 1966. Promoter Bill Graham got them a 45-minute afternoon slot at Woodstock on August 16, 1969, for $2,500, and that performance launched them to international fame. It was the same festival that ended with Jimi Hendrix’s famous Monday-morning set. Early hits such as “Evil Ways,” “Black Magic Woman” and “Oye Como Va” followed, and in 1998 the classic line-up was inducted into the Rock and Roll Hall of Fame.
But the hits had slowed down. After the band’s deal with Columbia Records ended in 1991, two albums for Polydor and Island sold poorly. In 1996, Carlos asked to be released from Island, telling label founder Chris Blackwell that he had “a masterpiece” album in him. Several labels showed interest, and some, the guitarist recalled, thought he was too old.
Back With Clive Davis
The answer was an old friend. Clive Davis, who had first signed Santana to Columbia in 1969, was now running Arista Records. After seeing the band’s new line-up at Radio City Music Hall, Davis offered a deal, on one condition: he wanted some creative input. His plan was half “vintage Santana” and half collaborations with younger artists. The album that came out of it, Supernatural, featured guests including Eric Clapton, Lauryn Hill, Dave Matthews, Everlast, Eagle-Eye Cherry, Maná and CeeLo Green. Its working title was Mumbo Jumbo, which was changed shortly before release.
From “Room 17” to “Smooth”
The song began as something else. Songwriter Itaal Shur had written a track called “Room 17,” but EMI felt its lyrics were too sexual, so the words were stripped off and the music was given to Rob Thomas, the singer of Matchbox Twenty. Thomas rewrote the melody and lyrics, came up with a new chorus within a few hours, retitled it “Smooth,” and recorded a demo for Santana.
Thomas did not plan to sing it himself. He saw “Smooth” as his first real step as a songwriter for other people, and George Michael was among the names considered for the vocal. It was Clive Davis and producer Matt Serletic, who had produced Matchbox Twenty’s debut album, who suggested Thomas should sing it.
Inspired by His Wife
Thomas said the lyrics were partly inspired by his wife, Marisol, who is half Spanish and half Puerto Rican, and partly by Santana himself. When he finished, he was not sure the song was any good. His wife listened to the demo and told him, “This is going to be huge.”
Carlos Santana heard the same demo and said that at first he could not tell whether the singer was a man or a woman. He had no idea who Thomas was, but he liked the voice and asked that Thomas sing on the record. When they finally met, Santana asked Thomas if he was married to a Latin woman.
Three Takes in Berkeley
“Smooth” was recorded at Fantasy Studios in Berkeley, California, and mixed at the Record Plant in New York. According to Thomas, it was recorded live, in three takes. He did not even know it would be a single until he heard it on the radio. The song went to radio on June 15, 1999, the same day Supernatural was released, with the physical single following in August. Some stations had already been playing a leaked copy since early June.
The video, starring Thomas, was played heavily on MTV and VH1. For Thomas it was a turning point: the exposure lifted him out of anonymity and introduced Matchbox Twenty to an older audience. As he later put it, “Smooth” “really opened up the door for me as a songwriter and a solo artist.”
Twelve Weeks at No. 1
“Smooth” climbed through the summer and fall and reached No. 1 on the Hot 100 dated October 23, 1999, replacing Mariah Carey’s “Heartbreaker” featuring Jay-Z. Then it simply stayed there. It held the top spot for 12 consecutive weeks, through the chart dated January 8, 2000, until Christina Aguilera’s “What a Girl Wants” took over. That made it the last No. 1 of the 1990s and the first No. 1 of the 2000s, and the only song to appear on two Billboard decade-end charts.
It was a fitting end to a decade of marathon No. 1s, the same decade in which Boyz II Men’s “End of the Road” set a record of its own. And 1999 had already given us debuts like Britney Spears’ “…Baby One More Time”, so “Smooth” was competing with a very different kind of pop.
A Record Thirty Years in the Making
Amazingly, “Smooth” was Carlos Santana’s first No. 1 single. His previous best on the Hot 100 was “Black Magic Woman,” which peaked at No. 4. The song hit the top thirty years after Santana first entered the Hot 100 with “Jingo,” the longest wait between an artist’s chart debut and their first No. 1.
The numbers kept growing. “Smooth” spent 30 weeks in the top 10, a record at the time that beat Savage Garden’s “Truly Madly Deeply” by four weeks, and 58 weeks on the Hot 100 in total. It also went to No. 1 in Canada and No. 3 in the UK and Ireland. The next single from the album, “Maria Maria” with the Product G&B, spent another 10 weeks at No. 1 in the U.S.
A Grammy Sweep and a Long Afterlife
At the Grammy Awards in 2000, “Smooth” won Record of the Year, Song of the Year and Best Pop Collaboration with Vocals. Supernatural won nine Grammys in total, including Album of the Year, and went on to sell an estimated 30 million copies worldwide, making it Santana’s best-selling album. In 2025 it was inducted into the Grammy Hall of Fame.
Billboard later ranked “Smooth” as the No. 2 song in the first 50 years of the Hot 100 and the No. 1 rock song in the chart’s history, and it was again No. 2 on Billboard’s 60th anniversary list. In the summer of 2016, the song found a new audience as an internet meme, with writers poking fun at its earnest lines about a “Spanish Harlem Mona Lisa.” Somehow, the joke only made people love it more.
Listening Tips
- Listen for the conversation. Notice how Carlos Santana’s guitar answers Rob Thomas’s vocal lines instead of just playing a solo at the end.
- Play the whole album. Supernatural moves from “Smooth” to “Maria Maria” and Eric Clapton’s guest spot on “The Calling.”
- Go back to the beginning. Pair “Smooth” with “Evil Ways” and “Oye Como Va” to hear how far the Santana sound traveled.
- Hear the singer’s other side. Try Matchbox Twenty’s Yourself or Someone Like You, the album that made Thomas a star first.
- Explore the decade. Browse more 90s Throwback and Rock stories.
“Smooth” Quick Facts
| Artist | Santana featuring Rob Thomas |
| Written by | Itaal Shur and Rob Thomas |
| Producer | Matt Serletic |
| Album | Supernatural (Arista, June 15, 1999) |
| Hot 100 No. 1 | 12 weeks, from the chart dated October 23, 1999, to January 8, 2000 |
| Before and after | Followed “Heartbreaker” by Mariah Carey; replaced by “What a Girl Wants” by Christina Aguilera |
| Weeks on the Hot 100 | 58, including 30 in the top 10 |
| Other peaks | No. 1 in Canada; No. 3 in the UK and Ireland |
| Grammy Awards | Record of the Year, Song of the Year, Best Pop Collaboration with Vocals (2000) |
Sources
- “Smooth” (Santana song) on Wikipedia (with its cited sources, including Billboard)
- Supernatural (Santana album) on Wikipedia
- Santana (band) on Wikipedia
- Rob Thomas (musician) on Wikipedia
- List of Billboard Hot 100 number ones of 1999 on Wikipedia
- Billboard Hot 100, October 23, 1999
- Official Santana website
Photo Credits
- Featured image: Carlos Santana in Leiden, the Netherlands, 1978 by Chris Hakkens, CC BY-SA 2.0, via Wikimedia Commons
- Featured image: Carlos Santana live in Hamburg, November 1973 by Heinrich Klaffs, CC BY-SA 2.0, via Wikimedia Commons
- Featured image: Rob Thomas at WonderCon in Anaheim, 2015 by Gage Skidmore, CC BY-SA 2.0, via Wikimedia Commons
- Featured image: Carlos Santana live in London, 2018 by Eddie Janssens, CC BY-SA 4.0, via Wikimedia Commons
- In-article image: Carlos Santana in Hamburg, May 1984 by Heinrich Klaffs, CC BY-SA 2.0, via Wikimedia Commons
- In-article image: Rob Thomas at the Tribeca Film Festival, 2010 by David Shankbone, CC BY 2.0, via Wikimedia Commons
