“Smooth” is a collaboration between Latin rock band Santana and Matchbox Twenty vocalist Rob Thomas. The song was written by Thomas, and Itaal Shur, produced by Matt Serletic and sung by Thomas. It won three Grammy Awards: Record of the Year, Song of the Year, and Best Pop Collaboration with Vocals. Not only was it the final number-one Hot 100 hit of the 1990s, it was also the number-two Hot 100 hit of the 20th century. “Smooth” is the only song to appear on two decade-end Billboard charts. As of 2018, “Smooth” is ranked the second most successful song of all time by Billboard.
“Smooth” was originally conceived by Shur as a song called “Room 17”. The lyrics were stripped off and the track was given to Thomas, who re-wrote the lyrics and melody and re-titled it “Smooth”, then recorded the song as a demo to play for Santana. After hearing the song, Santana decided to have Thomas record the final version. Matt Serletic (who produced Matchbox Twenty’s debut album Yourself or Someone Like You) produced the song and it was released from Santana’s album Supernatural. Thomas originally had George Michael in mind to sing the song.
Thomas wrote “Smooth” for his wife, Marisol Maldonado. He stated in interviews that the lyric “My Spanish Harlem Mona Lisa” was inspired by the 1972 Elton John song “Mona Lisas and Mad Hatters”, which includes references to the 1961 Ben E. King song “Spanish Harlem”.
“Smooth” became a chart-topping hit in 1999, spending 12 consecutive weeks at number one on the Billboard Hot 100 beginning with the October 23, 1999 issue. It was the first chart-topping song in Carlos Santana’s long-running career (his previous biggest hit being “Black Magic Woman”, which peaked at number four in 1971). The song stayed in the top ten of the Billboard Hot 100 for 30 weeks, a record only bested by “How Do I Live” by LeAnn Rimes, “Closer” by The Chainsmokersfeaturing Halsey, and “Shape of You” by Ed Sheeran. In the United Kingdom, “Smooth” first charted at number 75 in the UK Singles Chart in October 1999. On a full release in March 2000, it peaked at number 3, spending eight weeks in the top 40. The song also peaked at number 3 in Ireland in March 2000, spending ten weeks in the Irish Charts. It remains Santana’s highest charting single in either Britain or Ireland.
“Smooth” also spent a record-breaking ten consecutive weeks at the top of the VSpot Top 20 Countdown, a record that held up until the Dixie Chicks broke it in 2006.
On Billboard magazine’s rankings of the top songs of the first 50 years of the Billboard Hot 100 singles chart, “Smooth” was ranked as the number-two song overall (behind only “The Twist” by Chubby Checker) and the number-one rock song in the history of the chart.
In the 21st century, particularly during the summer of 2016, the song became popular as an internet meme. Writing for MTV.com, Sasha Geffen compared the situation to similar resurgences of “All Star” by Smash Mouth and “One Week” by the Barenaked Ladies, going on to attribute the song’s popularity to “the merits of its vocal absurdity.” She wrote, “There’s something ridiculous about how eagerly Rob Thomas lays his earnest alt-rock croon over Santana’s guitar, sweating out lines about how his ‘Spanish Harlem Mona Lisa’ is ‘just like the ocean under the moon’ without a hint of self-consciousness or irony’. In 2017, Tanya Sichynsky of The Washington Post similarly opined that “The opening lyric ‘Man, it’s a hot one,’… is a punchline that requires no set-up. The song was featured on two tracks, “Melt Everyone” and “Smooth Flow”, off of Neil Cicierega’s2014 mash-up album Mouth Sounds, and on two tracks, “Smooth” and “Shit”, off of the 2017 follow-up album Mouth Moods.