It is easy—perhaps too easy—to dislike “Smooth,” the Grammy Award-winning 1999 hit by Carlos Santana featuring Rob Thomas of Matchbox Twenty off the multi-platinum album Supernatural. The song's combination of tepidity and synthetic spice is like a dry English muffin misted with Tapatio. Its introductory drum fill, iconic to some, is gaudy and triggering to others. Even Santana himself wasn’t a fan when he first heard it.

Two years earlier, the 50-year-old guitarist was staring down a mid-career crisis. Despite years of steady output and critical acclaim, he felt out of touch with younger audiences and regretful that his teenage children no longer heard him on commercial radio. So, acting on the advice of his wife (and his longtime spirit guide, which he calls Metatron), Santana arranged to meet with the record producer Clive Davis at a lavish bungalow in the Beverly Hills Hotel. The two agreed that staging a proper comeback would require an arsenal of contemporary hits; and Davis, who signed artists such as Bruce Springsteen and Pink Floyd, believed he knew just how to get them.

“Give me half the album and trust that I will find material that is integral to your artistry,” Davis told Santana. “The other half of the album will be whatever you want it to be.”

The result was Supernatural, which featured a buffet of ‘90s hitmakers, including Wyclef Jean, Lauryn Hill, and Dave Matthews. “Smooth” was the very last single Davis and his team delivered to Santana, who at first thought it sounded too rough, “like a painting that needed to be completed,” he said. It also reminded him of “Guajira,” a slinking, piano-driven track with a similar intro, from his 1971 album Santana III. He wasn’t sure about the fit, or the vibe, or even Rob Thomas. It wasn’t the sort of song his band was in the habit of playing.

In retrospect, that was precisely the point. From the instant it hit U.S. airwaves in June 1999, the track seemed destined to jackhammer its way into America’s consciousness. Thanks to its key personnel—an aging virtuoso and a rising pop rock star—the demographic potential was almost comically broad. And although haters deny it, the song’s musicianship is slick and impeccable.

It also didn’t hurt that 1999’s pop music environment was uniquely primed for a hit of this magnitude. Latin pop crossovers were ascendant, with Ricky Martin’s “Livin’ La Vida Loca,” which debuted that March, as recent proof of concept. Meanwhile, U.S. album sales were soaring and Napster, the file-sharing service that would eventually firebomb much of the music industry’s critical infrastructure, was only a few weeks old.

Twenty years after its release, "Smooth" enjoys the gilded status of America’s second-most popular song of all time, right behind Chubby Checker’s “The Twist” and right above Bobby Darin’s “Mack the Knife,” according to Billboard. Its potency derives largely from the fact that it is impossible to not react to—whether with excitement, exasperation, derision, or muddled, semi-ironic affection. It was meme bait before memes even existed: the rare cultural product whose very existence morphed into a sort of provocation.

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Carlos Santana on the set of the 1999 music video shoot for Smooth in Harlem.

Such longevity, we hate to admit but know deep down, is a referendum on us. “Smooth” has woven itself into our cultural DNA. Yet to understand why, exactly, the song demands our acknowledgment (and, perhaps, even our respect), it’s crucial to first understand the mechanics of its creation and ascendance. For the last six months, I’ve been talking to the people involved in the song’s creation, including Santana, Thomas, and Davis. The story they tell is a bit of a paradox—a tale of both deep cynicism and wide-eyed idealism; of cold industry calculus and luminous virtuosity. It contains lessons about joy, anxiety, and luck, and how, every so often, the three combine to produce something eternal.

“This song belongs with something that people need every day in their lives: air, water and sex,” Santana says. “You can have food—granola, or whatever. But basically, air for your lungs, water for your body, and s-e-x for your psyche.”

Supernatural’s basic blueprint was cribbed from Deuces Wild, a 1997 album that paired B.B. King with a collection of established artists, including Bonnie Raitt, Van Morrison, and D’Angelo. Although that effort didn’t impress reviewers (Rolling Stone concluded that its “juke joint authenticity” was smothered by a “Ritz Carlton budget”), Supernatural’s creators thought they might improve on the idea.

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Marisol Maldonado, Rob Thomas's then fiancée, in the video for "Smooth," with Santana on guitar behind her.

Much of that improving fell into the hands of Pete Ganbarg, then an A&R executive at Arista Records. Shortly after Santana and Davis convened in 1997, he began a months-long process of refining songs and tracking down artists, at times combing through magazines for pop acts who said they grew up listening to Santana. Near the finish line, he hit a wall.

“I had this kind of dread in the back of my mind that even though we had a great album, we didn't have a first single that would open the doors for us,” he says. Also, the fiscal year was about to end, and he was still on the hook to sell tens of thousands of albums.

Just as Ganbarg was nearing a panic, he encountered the first of several lucky breaks that occurred during the creation of “Smooth”: Evan Lamberg, an industry friend, called out of the blue to ask if he still needed songs. Lamberg introduced Ganbarg to a young musician named Itaal Shur, who was developing a salsa track called “Room 17” about an illicit hotel rendezvous. Ganbarg loved the basic components, but he found Shur’s lyrics bizarre and kind of tactless.

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Pete Ganbarg, the A&R executive at Arista Records who brought "Smooth" to Supernatural.

“It was about a groupie meeting Santana after the concert in a hotel room,” Ganbarg recalls. “Which, if you know anything about Carlos Santana, is 180 degrees opposite of who he is.” (Shur, for his part, maintains the song was simply about two long-estranged lovers cheating on their significant others.) After some negotiations, Shur agreed to polish the track with Rob Thomas, who had just wrapped a tour with Matchbox Twenty and, in Ganbarg’s recollection, “was living in an apartment downtown in Manhattan with his girlfriend, and he was smoking pot and he was playing Playstation.” In other words: enjoying the trappings of a blossoming semi-stardom.

That Shur and Thomas worked so well together—and so quickly—turned out to be another happy accident. The two went from complete strangers to heads-down collaborators virtually overnight. Thomas changed the key of “Room 17” and added a chorus. He re-worked the lyrics to de-emphasize adultery and focus instead on a lusty yet G-rated commitment to his fiancée, the model Marisol Maldonado (eventually described as his “Spanish Harlem Mona Lisa”). It all felt easy, casual.

“It was pretty much songwriting 101,” Thomas says. “At the time, I didn’t think there was any significant moment happening there. We were just kind of in [Shur’s] apartment studio chilling out.”

Meanwhile, each tweak felt to Ganbarg like a form of pain relief, a chiropractic adjustment. He allowed himself to believe that maybe, possibly, “Smooth” could turn into the hit he so desperately needed—a song that could move both asses and records. When he played it for his boss Clive Davis, a notoriously tough critic, Davis agreed: They were onto something.

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Just one problem: Santana wasn’t interested. He required reassurances from Davis, who had first signed him in the 1960s, whose opinion he deeply respected, and who he had been chanting about, in compulsive sets of 27, during meditation sessions.

“So I have to go in sheepishly to Clive Davis’s office with my tail between my legs and say, ‘Clive, I need your help,’” Ganbarg recalls. “‘You’ve got to tell Carlos that this song is a hit, or else he won't record it.’” Davis dictated a note to Santana, which Ganbarg hurried off to fax. A few days later, Santana relented. He would record the song—as long as Rob Thomas did it with him, live.

“It was pretty much songwriting 101. At the time, I didn’t think there was any significant moment happening there.”

“I believed him a little bit, but I didn’t believe completely,” Santana says of Thomas. “Something happens when Brother Rob Thomas sings at the same time with the Santana band and myself in the same room. All of a sudden, two and two become seven instead of two and two becomes four.”

If there’s one thing that’s remarkable about the recording of “Smooth,” it’s how plainly unremarkable it all felt in the moment. Yes, Santana himself now describes the experience as a “tsunami of positivity,” devoid of egos and full of “EN. ER. GEE;” and yes, he gifted Rob Thomas an elaborate tapestry as soon as they walked into the studio; and yes, he asserts that the forces of gravity and time may have dissipated momentarily. But for many of the musicians involved, it felt routine—an-easier-than average session in service of a simple tune. They recorded live, ran through the track a few times, liked what they heard. Then they went home.

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Rodney Holmes, the drummer on "Smooth."

“I listen to it, and it's like, ‘Oh! it's like a song!’” says bassist Benny Rietveld. “We were used to just recording jams.”

“The only thing that I remember is just trying to get it to feel right,” adds drummer Rodney Holmes. “Just doing your job: You show up at the studio, you've learned the music. So now, it’s ‘Let’s execute.’ And that was it.”

Simple in theory. Yet it’s worth pausing for a moment to point out that the musicians on “Smooth” are not exactly a gaggle of toothless vagabonds, busking for quarters. They are elite, hall-of-fame-level players with eye-popping resumés and decades of experience. This is perhaps an obvious point, but it’s also one of the most important—and overlooked—aspects of the song’s success.

Consider, for example, keyboardist Chester Thompson, who played with the precision-funk outfit Tower of Power for years before joining Santana’s band; or trumpet player Julius Melendez, who spent a decade in the U.S. Navy band before a stint with the Grateful Dead; or Rietveld, who in the 1980s toured around the world with Miles Davis.

All the calculated machinations and luck and chemistry powering “Smooth” up to this point would have meant nothing without this trove of talent. Santana’s musicians weren’t just hired guns. Through years of playing together, they’d developed little cues and signals and in-jokes—a whole dialect whose phrases and fragments are sprinkled throughout the song. This is apparent when the entire percussion section, acting with one shared brain, pulls back the timing on the iconic introductory drum fill, almost like a slingshot. Or listen to how the bass and keys seem to coquettishly beckon you forward, or how the track sustains its precise momentum, even as its outro explodes into unbridled chaos.

“We play like there’s no tomorrow,” Santana says. “We play like if you’re gonna get a heart attack by getting to that note, then gosh darn it, get the heart attack. But get the note.”

Everyone agreed the song sounded like a hit. But executives at Arista were still worried about the mechanics of selling America on something new from Santana. So they made a shrewd choice: When distributing the single, they left off the guitarist’s name, marking the CDs simply as “Smooth” and “Mystery Artist.”

Soon, the song’s magnitude, its infectious omnipresence, began to dawn on the creators themselves. For some, the realization came through blunt repetition: hearing it in the grocery store, then in a nearby pharmacy shortly thereafter. Others flipped between radio stations that were playing it simultaneously, or heard it blasting from a beat-up Pontiac in Hawaii, or were simply told by their wives: This could actually be something.

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Carlos Santana and Rob Thomas onstage at the Andre Agassi 12th Annual Grand Slam for Children on October 6, 2007 in Las Vegas.

Rob Thomas’ own “aha” moment was goofy and cinematic. “It was one of those weird things that never happens anymore,” he says. “I was just walking down West Broadway and I stopped at a crosswalk, and this car full of hot girls—a convertible—pulled up at the red light and they were blaring ‘Smooth.’ It took me a second to realize what I was listening to. So my first thought was, when I see a bunch of hot girls in a car listening to it, there’s something happening here.” Two days later, in Los Angeles, he was walking through a hotel lobby. “This big fucking guy, just fully tatted, this crazy dude, comes running over to me and he’s like, ‘That fucking Carlos track is on fire, man! Good job!’ I was just like, ‘Oh shit! All right. That’s something.’”

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Carlos Santana with producer Clive Davis.

The song was released as a single on June 29, 1999. It was certified gold by September 13 and platinum by November 9. It was the first number one song of Santana’s career, and it stayed at the top of Billboard’s Hot 100 for 12 consecutive weeks (and in the top 10 for 30 weeks). Then it topped the charts in 10 other countries. At the following year’s Grammy Awards, it won Record of the Year, Song of the Year, and Best Pop Collaboration with Vocals. Santana won Album of the Year for Supernatural, Best Pop Collaboration with Vocals, Best Pop Performance by a Duo or Group With Vocals (for “Maria Maria”), and Best Pop Instrumental Performance (for “El Farol”). Nine Grammies in total.

The awards provided a deluge of delayed recognition for Santana, a living legend who over his decades-long career had only won once, in 1988, in the Best Rock Instrumental Performance (Orchestra, Group or Soloist) category. In one photo from the evening, Thomas, Santana, and Clive Davis cradle their statues, each wearing a befuddled smile. Santana, in particular, looks ecstatic. The awards teeter cartoonishly in each man’s arms, as though the Recording Academy had backed up a dump truck and deposited them.

In the expansive canon of American popular music, there are various species of earworms. Some are harmless; some are venomous. Some wriggle in and out in mere minutes. The most powerful kind, though, are those that stick around despite a hapless listener’s best efforts at self-preservation. You really have to hand it to these fuckers: They enter the brain and immediately make themselves at home. They hang pictures, arrange furniture, sign a long-term lease. It goes without saying that they never, ever move out.

What do you feel when “Smooth” comes on at a wedding, or at a grocery store, or in your cousin’s 1998 Mazda Miata? Is it joy? Repulsion? Nostalgia? Some inarticulable slurry of the three?

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Rob Thomas, center, with his band Matchbox Twenty in Chicago.

The best parallel to my own reaction comes from another 1990s touchstone. In one episode of The Simpsons’ seventh season, Homer discovers that he can withstand being shot in the belly with a cannon. On the strength of this skill (and against the advice of his doctor), he capitalizes on the gimmick, earning temporary fame that culminates in an appearance on the bill at “Hullabalooza,” Springfield’s send-up of Lollapalooza. Before Homer appears onstage, there’s a shot of two teens in the crowd.

“Oh, here comes that cannonball guy,” one of them says. “He’s cool.”

“Are you being sarcastic, dude?” his friend replies.

A quick wave of panic flashes over the first teen’s face, then a look of resignation. “I don’t even know anymore.”

Like the cannonball gimmick, “Smooth,” as a cultural product, scrambles our receptors. Its omnipresence has created a nearly infinite spectrum of strong affinities and hostilities, some of which are difficult to parse. It remains fertile for parody—whether with memes that inquire whether today is, in fact, “a hot one,” or with T-shirts that proclaim: “I’d rather be listening to the Grammy Award-winning 1999 hit Smooth by Santana feat. Rob Thomas of Matchbox 20 off the multi-platinum album Supernatural.” At its worst, it is a tongue-in-cheek weapon to be deployed at captive audiences (dinner parties, car passengers); at its best, a colossal hit, crafted with equal parts joy, virtuosity, and cold calculation. In the middle, where most of us reside, it is the largest and most inclusive in-joke of all time. In all cases, the best approach is to simply surrender.

“Here’s the key to miracles and blessings,” Santana says. “Do you have the willingness to allow the spirit to come in? And do you have the discipline to get out of the way?”

So yes, it is possible to hate “Smooth” for the cynical mechanics of its creation, for its permanent residence in our heads and homegoods stores, for the line about a “Spanish Harlem Mona Lisa.” Yet because the song’s success is self-inflicted through decades of our own weddings and parties and makeout sessions, any hatred is also, by definition, a form of self-hatred.

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Thomas and Santana attending the 42nd Annual Grammy Awards in 2000.

None of this, by the way, is lost on its authors, who like you and I cannot seem to escape it. They continue to hear it at Whole Foods, on their own device’s shuffle function, on commercial radio, and when they are traveling in other countries.

“Even today, in all honesty, I’m OK if I never hear that song,” Thomas says. “When I say that, I love playing it and I love performing it. And I would play it every night, and I have a great joy every time that I do it. But I’m OK if I don’t hear it again.”

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