The Story of the T-Shirt That Captured Our Obsession with Santana's 'Smooth'

Man, 1999 was a hot one.

There wasn't a corner of this earth, it seemed, that wasn't invaded by the hottest song of the summer: "Smooth" by Santana, featuring Rob Thomas of Matchbox 20. The song—and its video—was a sweltering, Latin-drenched pop-rock banger. You could tell white boy Rob got his first taste of seasoning—from his then-girlfriend and now-wife, a Latinx woman who inspired the lyrics to "Smooth"—and he loved every second of it. "Smooth" swirls in your brain and invades your pelvic area, forcing you to swivel around in your office chair as I now have for the past two hours (and counting!) that I've been listening to the song as I write this, pummeling myself with Santana's gripping Latin-blues riffs and Rob Thomas's hard u's when he sings "reason for reaso-huuuun" or "oceauun." (I only stopped when I had to use the bathroom, but after the 20th play, I considered just pissing myself to Rob Thomas' magnetic post-grunge voice and its inability to pronounce "barrio.") After the 30th play, I decided I might be losing my mind. Currently, I'm numb to all but one thing I know now to be true: This is going to fuck up my Spotify recommendations.

In 2000, that summer before I entered 10th grade, the song was inescapable, and listening to it on repeat reminds me of feeling like the Spanish Harlem Mona Lisa it made us all once believe we could be. On February 23 of that year, the completely expected happened: Carlos Santana swept the Grammys, winning eight awards (tying Michael Jackson's record for Thriller) that fateful night for his LP Supernatural, which featured a little ditty called "Smooth." The summer jam formed part of the Latin Explosion of 1999, ushered in by the popularity of Ricky Martin's "Livin' La Vida Loca," and earned Santana, Thomas, and co-writer Itaal Schur some of the night's top prizes (Record of the Year, Song of the Year, and Best Pop Collaboration with Vocals). This week marks the 20-year milestone for Santana's epic Grammy night, about which the legendary Mexican musician and women's footwear designer told Rolling Stone, "It was very daunting to not be there for 30 years and all of the sudden, one day, they give you everything."

Supernatural has since been certified 15 times platinum, and "Smooth" spent 12 weeks at the top of the Billboard Hot 100. We ended 1999, survived the Y2K bug that was supposed to end humanity, and entered the new millennium with "Smooth" as our soundtrack. And since then, "Smooth" has enjoyed a resurgence within internet culture as an ironically beloved, oft-memed song that now lives in the annals of online humor alongside Smash Mouth's "All Star."

The enduring legacy of "Smooth" has been captured most succinctly in a now-infamous T-shirt—the I'd Rather Be Listening to Grammy-Award Winning 1999 Hit "Smooth" By Santana Feat. Rob Thomas of Matchbox Twenty shirt. (There are also bootlegs of this original design which read I'd Rather Be Listening to Grammy-Award Winning 1999 Hit "Smooth" By Santana Feat. Rob Thomas of Matchbox Twenty Off the Multi-Platinum Album Supernatural.) With its inane verbosity that channels the snarky affections of online culture, the shirt itself has also become an iconic symbol of memedom.

Back in December 2015, Nicholas Kula was in college, working on a math degree and minoring in electrical engineering and linguistics. He also had a full-time school job and a part-time off-campus job. "Memes were like the only thing keeping me sane," the 38-year-old guitar effects pedal designer and writer told VICE. "This was kind of when memery really got cooking and it really started to permeate mainstream culture. The shirt came out of a melting pot of those ideas."

"But why 'Smooth?'" I asked Kula. Why not an I'd Rather Be Listening to "All Star," or "Sandstorm," or "Bring Me to Life" shirt? What made "Smooth" so worthy of the effort?

Like many moms of that time, Kula's mother had a CD wallet in her car that contained Santana's Supernatural. "Needless to say, she wore it out when I was younger. I think I heard that song 10,000 times," said Kula, noting that his mom was also a fan of Matchbox 20’s Yourself or Someone Like You. Plus, Kula agreed that "Smooth" is "objectively good" and "Santana ain't no hack."

"I think verbosity is super funny when the source idea is really ridiculous, and I originally made the shirt for myself to purchase on the site Redbubble. But then out of the blue, people started buying it. I only sold a few of them before the bootleg started getting posted all over; then it just took off," he further explained.

That's when the bootlegs started rolling out. Kula noted that you can tell the bootlegs apart from his design because of the spacing and their inclusion the album title, which he said "just felt tacked on. It’s like a Bloody Mary with hamburgers and pizza slices poking out of it." Kula sent out about 200 DMCA notices (which informs a company that they're hosting material that infringes on copyright material), and even tried changing his listing to note his design was "the ORIGINAL" but copycats just added "the ORIGINAL" to their posts also. Those sneaky bastards!

Ultimately, and painfully, it was none other than Rob Thomas who shut down Kula's "Smooth" shirt operation; strange, considering Thomas has shown his support of the shirt on Twitter. Kula got a cease-and-desist letter from Thomas's merch company, Firebrand Live, in August 2017. He wrote a six-page appeal that included links to fair use laws, but nonetheless, Kula got shut down.

"I tweeted at Rob Thomas offering to manufacture the shirts and split the profits and he didn't even read it," Kula said. "He should have sold them! With his audience, he would have raked it in."

In the end, Kula made about $1,000 off the shirt, but more importantly, he's now responsible for the creation of an internet legend, worn by countless fans—ironically or not—of the song. But sadly, he never got a shirt of his own. He'd figured he'd be able to buy one whenever, then suddenly, it was too late.

"Maybe one day I’ll swallow my pride and buy one off a bootlegger just to put in the closet," he said. If that ain't just like the ocean under the moon, I don't know what is.

Alex Zaragoza is a senior staff writer at VICE who refuses to change her life to better suit anyone's mood.