Born Walter Theodore Rollins in New York City in 1930 to parents from the Virgin Islands, he grew up in Harlem. He began on piano, tried alto sax, then at 16 switched to tenor to emulate Coleman Hawkins. Early in his career he played with the likes of Babs Gonzales, J.J. Johnson, Bud Powell, Miles Davis and Thelonious Monk, whom he called his "musical guru."
In the 1950s Rollins battled heroin addiction and faced multiple arrests before receiving treatment at the Narco Farm in Lexington, Kentucky. After moving to Chicago he rebuilt his career and between 1956 and 1958 released 16 albums, including the celebrated live A Night at the Village Vanguard. A later sabbatical and long walks across the Williamsburg Bridge led to his 1962 album The Bridge.