Carlos Santana’s biggest hit single in 1999 was “Smooth.”
“Smooth” was performed by Santana featuring Matchbox Twenty singer Rob Thomas. It became the lead single from Santana’s 1999 comeback album, Supernatural, which paired the veteran guitarist with younger contemporary artists and introduced his music to a new generation.
The track was released to radio in June 1999 and became Santana’s first No. 1 single on the Billboard Hot 100. It remained at the top for 12 consecutive weeks and finished as the longest-running No. 1 single of 1999. The song also won three Grammy Awards in 2000.
The other listed titles are important Santana songs but do not answer the question. “Black Magic Woman” was a major earlier hit, while “Oye Como Va” became one of Santana’s signature recordings. “Maria Maria” was another successful Supernatural-era single, but “Smooth” was the defining 1999 chart hit.