13 Things You Didn’t Know About Rob Thomas and Carlos Santana's 1999 Hit 'Smooth' (Exclusive)

Rob Thomas and Carlos Santana
L. Busacca/WireImage for J Records

ET is celebrating Rob Thomas and Carlos Santana's hit song, 'Smooth,' on its 20th anniversary.

As pop princesses and boy bands exploded onto the charts at the turn of the millennium, one song crept out of nowhere to sit atop the Billboard Hot 100 for 12 consecutive weeks. Twenty years later, chances are if you go anywhere this weekend -- whether it be a wedding, a birthday, a bar or even the grocery store -- Santana and Rob Thomas’ smash hit, “Smooth,” will play at some point.

“The song has brought so much joy to so many people,” the song’s co-writer, Itaal Shur, reflects. “Every bar mitzvah, wedding, cruise ship and anywhere there’s a live band, it’s on the set list. It’s universally loved. What I’m most proud of is that it’s touched people of multi-generations, which feels like the greatest achievement -- to make music that can cross age groups.”

At the time, Santana frontman Carlos Santana was 51 and hadn’t had a hit single in over a decade. Eager to get his music played on the radio again, he turned to music executive Clive Davis, whom he had worked with during his heyday. The two pulled in musicians like Lauryn Hill and Eric Clapton while recording the band’s 18th studio album, Supernatural, but felt they still needed one big song to launch the record with.

At a time when Latin American pop from the likes of Ricky Martin, Enrique Iglesias, Shakira and Jennifer Lopez was blowing up, “Smooth” re-cemented Santana’s place as one of the ultimate and defining voices of Latin music. “Rediscovering that Carlos was one of the original, authentic voices of Latin music and reintroducing it to a new generation is what happened with that song,” “Smooth” producer, Matt Serletic, says. “It was amazing to watch and be some small part of that culture exploding onto a more nationwide scene. I think that’s why people are writing about ‘Smooth’ all these years later. There’s some level of authenticity, where even if you mock it or call it cheesy, ultimately Carlos as a grounding factor is truly Latin, and his band and the artistry and all the things you look for to make live music feel real and purposeful are in this song.”

Shur admits that he never expected the single to blow up, given the bubblegum pop dominating radio at the time.

“I didn’t think it would be popular because Santana wasn’t a young artist and by that time in the music business, you started to see less career artists coming back -- it became a younger and more disposable world by the late '90s,” he says. “But I started to hear ‘Smooth’ a lot on the radio, then when it started climbing up the charts quickly, I was like, ‘Oh my god. This is crazy.’”

To celebrate the 20th anniversary of “Smooth” on June 29, here are 13 fun facts about the three-time GRAMMY-winning track.

The missing rhythm

With Supernatural completed except for a launching single, Shur was called upon and stopped by A&R executive Pete Ganbarg’s Arista Records office to hear the record, which gave him a sense of the missing piece of the puzzle. “What was missing, in my opinion, was that ‘Oye Como Va’/’Black Magic Woman' sound,” Shur says, referring to Santana’s older hits. “It’s called ‘montuno,’ which is that basic Cuban rhythm, which Santana popularized by giving a mix of rock. I felt that basic groove was missing from the album and thought, ‘Everybody’s doing hip-hop and all these different things, but I’m going to be a traditionalist.’”

Sheryl Crow's "All I Wanna Do"

The underlying sound of the song was further influenced by Sheryl Crow’s 1994 hit, “All I Wanna Do.” “Certain songs you get influenced by and that was a really big one for me,” Shur says. “There was also a song by Donny Hathaway called ‘The Ghetto’ which was a big influence too. They both had this groove I wanted to do and I wanted it to be a universal thing where everybody -- young, old and in-between -- could get into it.”

While Crow may not have known she played a small part in the smash, she joked about the song and album’s awards sweep at the 2000 GRAMMYs, where she accepted the award for Best Female Rock Artist while thanking Santana “for not being in this category.”

The original track was titled “Room 17”

With just one weekend to write his potential hit, Shur turned to a “grab bag” of songs he had started penning for his own band and was drawn to one called “Room 17.” He says the track was about two former flames who had grown up and moved on with life but wondered if they still had a connection, so they decide to meet in a hotel room one night. Staying up all weekend to create a demo, he delivered it to the label on Monday morning. “It’s a testament to keeping your ideas in your little folder, and when opportunity knocks -- be ready,” Shur says.

A neighborly rewrite

While everyone loved the track, no one was into the lyrics, so Shur swallowed his pride and allowed Ganbarg to send the instrumental to Thomas, who had just come off the success of Matchbox Twenty’s debut album, Yourself or Someone Like You. “I could’ve said, 'You don’t like my song, I don’t want to do this,'” Shur says. “It was hard for a couple of seconds, but I had a feeling it was the right thing to do. Sometimes songwriting’s similar to a screenplay, where you come in with your idea and they want to change things to appeal to a wider audience.”

Thomas penned new verses, then convened with Shur to work on the chorus. The two had never met but instantly hit it off. “He came over and we just got along really well,” Shur recalls. “He was living two blocks away, which I didn’t know, so it was kind of neighborly.”

“When I heard Rob’s version, it started to turn into something totally different,” he adds. “Pete liked it, so I started liking it. Sometimes you’re not sure how you feel, but you can see people are responding positively and start picking up that energy.”

Spanish Harlem Mona Lisa

While Thomas says he started out writing lines like, “You’re so smooth” about Santana, he eventually became inspired by his stunning Puerto Rican love, Marisol (his fiancée at the time, with whom he will mark 20 years of marriage in September), like the line, “My muñequita, my Spanish Harlem Mona Lisa.”

“I had this wealth of information because I had this smokin’ hot Latin girlfriend already,” he recently told Rolling Stone

“Rob was living in SoHo in this white-walled apartment and it was his first real apartment because he came from not having much money,” Serletic says. “He was in there with Marisol and I just remember hearing that line for the first time and thinking, ‘Oh, that’s her. That’s awesome.’ It’s one of those lines that grabs you. That’s why the song stands the test of time -- it’s striking thanks to lines like that.”

Rob who?

With the lyrics sorted, it was finally time to take the track to Santana. But he wasn’t thrilled when he heard it, and even after Davis convinced him to record the song, he questioned why he would get “demo singer” Thomas to feature on the track. “Carlos definitely had a tepid reaction to the song, and then he wasn’t sure about the singer,” says Serletic, who had worked with Matchbox Twenty on Yourself or Someone Like You. “He didn’t know who Rob was and what Matchbox had done so far probably didn’t penetrate his radar -- Rob was just a demo singer to him. I vividly recall mine and Clive’s first phone conversation with Carlos, saying, ‘Rob can do this. Rob can make a record with you that will be exciting and the two of you will be good together. I know he can bring it!'"

Record recording time

Despite Santana’s doubts about Thomas, the two knocked the song out in no time after meeting at Record Plant studios in Sausalito, California. “I had met him once at a festival, but then we did ‘Smooth’ live over two days in the studio in San Francisco, so that’s when we really got to hang out, while we recorded the song,” Thomas tells ET.

Serletic recalls how Santana helped break the ice with an evidently nervous Thomas as the two arrived in the evening. “Carlos shows up and Rob shows up and Carlos has got his team and Rob’s by himself,” Serletic says. “He was a bit nervous as any young artist meeting a legend is, especially when his whole band’s there and the incense is flowing and all of that. I introduced them and Carlos was like, ‘We’re going to make magic together.’ What was crazy was from that first, ‘Hey, I’m Rob,’ it was like an hour later that we were cutting a record that we’re talking about 20 years later. It was very quick -- literally, take two was the master take.”

Santana decides to re-record all his guitar solos

Although the recording session ran fast and smooth, Serletic had a “freak-out moment” when Santana walked in the next morning declaring he wasn’t happy with the sound of his guitar solos. “He was like, ‘I don’t like my tone,’ and kept doing this thing where he would put his thumb on his canine teeth and say, ‘It sounds like tin foil on my teeth!’ I was thinking, ‘Oh sh**. No!’ So, we started recording more guitar parts with a really dark tone and finally after an hour, he put his guitar down and said, ‘I like it how it was,’ then put his hands together in a prayer, bent down, bowed and said, ‘It’s done.’ That was one of the most fun, delightful things -- to see Carlos Santana bowing to me while saying, ‘OK, we’re good!’”

Napa Valley wine

With some time to kill before his next studio session, Serletic decided to take a little road trip. “It was Rob and Marisol and me and my wife’s first time together near Napa Valley so we went, ‘Let’s go see what wine country is!’” recalls Serletic, who now runs music technology company, Zya. “I hadn’t written the horn parts yet, so I just remember driving back scrambling and running so late because we drank too much wine at Stags' Leap Winery. I’m writing horn parts in the back of the car at 2.28 p.m. while Rob’s driving us back for a session that started at 3 p.m. Or maybe we had a driver -- Rob should not have been driving! I was just focused on what the horns would be in the second verse, but it was fun and some of that gut reaction stuff can make for the better record. The horns were arranged by Stags' Leap!”

Celine Dion’s record must go on

Serletic flew back to L.A. to work on “Smooth” during two free days he had before his next session, for Celine Dion’s “I Want You to Need Me.” However, an AM radio sound effect which he used on “Smooth” ignited debate at the label, and Davis wanted to weigh in on mixes as they were completed. Unfortunately, technology wasn’t advanced enough for Serletic to leave “Smooth” on the mixing board while moving onto Dion’s song.

“It became a process of, ‘Where in the world is Clive?’” Serletic recounts. “Meanwhile, I had this band on the floor waiting to cut a Celine Dion record, but I couldn’t plug them into the same console that had ‘Smooth.’ So, then I’m rehearsing the band on the floor like we’re in a garage -- when we’re actually in this multimillion-dollar studio which we can’t use because we’re waiting on a mix to be approved! I remember thinking, ‘Hell, I’m going to have to tell [music executive] Tommy Mottola that I didn’t finish the Celine Dion record because we’re arguing over an AM radio effect!’ Luckily, we still got it done.”

Jennifer Lopez steals some GRAMMYs thunder

The song won three awards at the 42nd Annual GRAMMY Awards in 2000 (Record of the Year, Song of the Year and Best Pop Collaboration with Vocals), where Shur took the stage with Thomas to accept Song of the Year. And, while he says they later hit up “all the parties” to celebrate, their moment of glory in the press room was upstaged by Jennifer Lopez and that dress -- the deep-plunging, green Versace gown, which remains one of the singer’s most memorable fashion moments.

“I had just won Song of the Year and afterwards you go backstage into the press room and in front of me was Jennifer Lopez and P. Diddy and she was wearing that famous green dress,” Shur recalls. “She wasn’t up for any awards, but she presented, then walked through the press room and it was just this big explosion of flashes. Then I walk in and they go, ‘What are you here for?’ I think maybe two flashes went off. I was pretty unamazing after her. Even with the Song of the Year award, you can’t follow Jennifer Lopez!”

Songwriter, Itaal Shur, musicians Rob Thomas and Carlos Santana, and music executive Clive Davis at the 2000 GRAMMY Awards. - Scott Gries/ImageDirect

GRAMMY grudges

The song's Record of the Year win meant a loss in the category for TLC’s “No Scrubs,” Cher’s “Believe,” Ricky Martin’s “Livin’ la Vida Loca” and the Backstreet Boys’ “I Want It That Way,” written by Max Martin and Andreas Carlsson -- something Shur would get gibed about years later. “I went to a dinner in Sweden two years ago and sat next to Max Martin and he said, ‘Yeah man -- you stole the GRAMMY away from us because I wrote ‘I Want It That Way!’” Shur shares. “It was pretty funny when he said that.” Martin wasn’t the only one peeved that “I Want It That Way” missed out, with some Backstreet Boys fans begrudging “Smooth” to this day. Yet, the award couldn’t come between Thomas and the boy band.

“There was no love lost at all,” says Leigh Dorough, wife of Backstreet Boy Howie Dorough. “Howie and I had a chance to hang and really get to know Rob and his wife Marisol a few years back at the Kentucky Derby. We developed a friendship -- they are truly an amazing couple.”

Meanwhile, Thomas posted multiple tweets celebrating the Backstreet Boys’ recent DNA album release. Two decades later, the Backstreet Boys will kick off the American leg of their DNA World Tour in Washington, D.C., on July 12, the same night that Thomas stops by the nation's capital on his Chip Tooth Smile tour -- and both acts will be performing the smash singles that got them nominated for 1999’s Record of the Year.

A sweet bromance 

While Santana may have had his doubts about Thomas 20 years ago, today the two couldn’t be closer. “Carlos and I were up the other night until three in the morning texting each other, sending pictures of our album covers and going back and forth about stuff we’re excited about,” says Thomas, who also remains close with Serletic and Davis. “The friendship has stayed very strong over the years. Having both him and Clive Davis as mentors is invaluable and to have the friendship on top of that is awesome.”

Thomas gushed further about Santana during his recent Chip Tooth Smile tour show at L.A.’s Greek Theater, explaining how the legend regularly checks in on him. “He’ll be like, ‘Where you at?’ and I’ll say, ‘I’m at The Greek in Los Angeles,'" Thomas told a packed crowd which included Hilary Duff, Malin Akerman, Ryan McPartlin and Bachelor Nation couple Ashley Iaconetti and Jared Haibon. “And, every time he asks me the same question. He says, ‘Did you bring your gratitude?’ And, the truth is, I look out here and I see people from six to 65 -- I see 20 years of our life going by here, from Matchbox and solo -- I see a lot of love that keeps coming my way, man, and it means everything to me, so I have my gratitude and I brought it and I give it to you tonight. So, this song ['Smooth'] goes out for you and Uncle Carlos.”

Days later, the two celebrated the song’s anniversary at the Phoenix, Arizona, stop of Santana and The Doobie Brothers' Supernatural Now tour, where Thomas surprised the audience by joining Santana on stage for a performance of “Voodoo Child” before coming back for a highly anticipated “Smooth” reunion.

“We’re both touring and we’re on different schedules but we want to do a couple of shows together, so we’re going to do what we can to make it work,” Thomas told ET before arranging the performance.

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