Tony- and Grammy Award-winning lyricist Sheldon Harnick, who with composer Jerry Bock made up one of the premier musical-theater songwriting duos of the 1950s and 1960s with shows such as Fiddler on the Roof, Fiorello! and The Apple Tree, has died. He was 99.

Known for his wry, subtle humor and deft wordplay, Harnick died in his sleep Friday (June 23) in New York City of natural causes, said Sean Katz, Harnick’s publicist. Broadway artists paid their respects on social media, with Schmigadoon! writer Cinco Paul calling him “one of the all-time great musical theater lyricists” and actor Jackie Hoffman lovingly writing: “Like all brilliant persnickety lyricists he was a pain in the tuchus.”

Bock and Harnick first hit success for the music and lyrics to Fiorello!, which earned them each Tonys and a rare Pulitzer Prize in 1960. In addition, Harnick was nominated for Tonys in 1967 for The Apple Tree, in 1971 for The Rothschilds and in 1994 for Cyrano — The Musical. But their masterpiece was Fiddler on the Roof.

Bock and Harnick were first introduced at a restaurant by actor Jack Cassidy after the opening-night performance of Shangri-La, a musical in which Harnick had helped with the lyrics. The first Harnick-Bock musical was The Body Beautiful in 1958.

“I think in all of the years that we worked together, I only remember one or two arguments — and those were at the beginning of the collaboration when we were still feeling each other out,” Harnick, who collaborated with Bock for 13 years, recalled in an interview with The Associated Press in 2010. “Once we got past that, he was wonderful to work with.”