Les McCann, a legendary soul-jazz pianist and singer whose work was often sampled by hip-hop producers, has died. McCann’s manager told NBC News he died Friday at a Los Angeles-area hospital after contracting pneumonia a week before. He was 88.

McCann was born into a musical family in Lexington, KY in 1935. He was self-taught on piano and also played drums and tuba growing up. While serving in the Navy in the 1950s, he won a singing contest, which led to an appearance on The Ed Sullivan Show. After leaving the Navy, he moved to Los Angeles and began his performance career in the early 1960s. He got a boost by catching an endorsement from Miles Davis, but his big breakthrough came in 1969 with the release of the live album Swiss Movement with saxophonist Eddie Harris, recorded at that year’s Montreux Jazz Festival. Their performance of the Vietnam war protest song “Compared To What” — also recorded by McCann’s collaborator, Roberta Flack — became a hit, helping the album to go gold.

As the ’60s rolled into the ’70s, McCann, who had always infused his music with a touch of soul from the Black church, became a pioneer of soul-jazz and was one of the first jazz musicians to incorporate electronic music into his work. He suffered a stroke while onstage in Germany in 1995, but he continued to perform for years despite paralysis on the right side of his body. By that point, hip-hop producers had already discovered McCann’s catalog as a goldmine for samples. A directory on his website lists McCann songs sampled by A Tribe Called Quest, Dr. Dre, the Notorious B.I.G., Mobb Deep, Massive Attack, ScHoolboy Q, Pete Rock & C.L. Smooth, and many more.

Below, check out some of McCann’s work.