In 1938 Terry was invited to play at Carnegie Hall for the first From Spirituals to Swing concert, and later that year he recorded for the Library of Congress. He recorded his first commercial sides In 1940. Some of his most famous works include "Old Jabo", a song about a man bitten by a snake, and "Lost John", which demonstrates his amazing breath control.
Despite their fame as "pure" folk artists, in the 1940s Terry and McGhee fronted a jump blues combo with honking saxophone and rolling piano, which was variously billed as Brownie McGhee and his Jook House Rockers or Sonny Terry and his Buckshot Five.
Terry was also in the 1947 original cast of the Broadway musical comedy Finian's Rainbow He also appeared in the film The Color Purple, directed by Steven Spielberg. With McGhee, he appeared in the 1979 Steve Martin comedy The Jerk. Terry collaborated with Ry Cooder on "Walkin' Away Blues". He also performed a cover of Robert Johnson's "Crossroad Blues" for the 1986 film Crossroads.
Terry died of natural causes in Mineola, New York in March 1986, three days before Crossroads was released in theaters ,He was inducted into the Blues Hall of Fame in the same year.