1999. Carlos Santana was washed up. His previous album barely scraped into the charts at #191. But a little collab with Matchbox 20’s Rob Thomas was about to change that: “Smooth.” Their banging bop topped the Billboard Hot 100 for 12 weeks and was ranked as the second-most-successful song ever on Billboard’s Hot 100 60th Anniversary listing. Quite the turnaround. If you were around in the ‘90s, you heard it plenty of times on the radio.
But did you know that the sizzling chemistry between Rob’s voice and Carlos’s guitar that made the genre-crossing hit such a success sounds even more legendary live? 56 million fans found that out listening to this live performance of one of the most iconic collabs of the ‘90s. The Music Man has to say that Latin music and alt rock have never been fused better than what these two legends did right here! There’s something about the primal energy Rob delivers that mixes so perfectly with Carlos’s wizardry.
Fan channel Nea Zixnh uploaded Santana’s and Rob’s 1999 live performance of “Smooth,” noting that it came from the guitarist’s concert film, A Supernatural Evening with Carlos Santana & Friends. Fans found a tonne to like here and added comments such as “This collaboration was magic! Rob totally in the sway and heart of Carlos’s vibe…. Still get chills hearing this years later!” and “One of the most perfect songs ever made. No matter what kinda music you’re into, everyone vibes with this song. It’s timeless.”
Any time Rob kicks out the jams on “Smooth” it’s always a treat for fans. The Matchbox 20 frontman dropped into The Song TV to perform his classic hit in April 2026. Rob is 54 here, but it’s sure hard to tell. Fans were amazed by the performance, noting that he looks and sounds like he’s in his 30s. And can we just say the X-factor Rob delivers any time he sings this song is so perfect? We also have to give it up for the band here for delivering a slithering groove on this classic song.
Santana and Rob Thomas dropped “Smooth” on June 15, 1999. The band issued the song as the lead single from their 18th studio album, Supernatural. The Music Man readers might be interested that it was written by American songwriter Itaal Shur and Rob. Itaal wrote the base song, and then Rob rewrote the melody and lyrics. “Smooth” has the distinction of being the last number one hit on the Billboard Hot 100 of the ‘90s, and also the first number one hit of the 2000s. It topped the chart in October 1999 and held the position for 12 weeks, ending its run in January 2000.