"Smooth" is a collaboration between Latin rock band Santana and Matchbox Twenty vocalist Rob Thomas. The song was written by Thomas, DeGaetano, 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 2013, "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 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".

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