Little Walter made his first released recordings in 1947 for the tiny Ora-Nelle label in Chicago. These and several other early recordings, like many blues harp recordings of the era, owed a strong stylistic debt to pioneering blues harmonica player John Lee "Sonny Boy" Williamson (AKA
Sonny Boy Williamson I). Little Walter joined
Muddy Waters' band in 1948, and by
1950 he was playing on Muddy's recordings for
Chess Records; Little Walter's harmonica is featured on most of Muddy's classic recordings from the 1950s. He also recorded as a guitarist for the small Parkway label, as well as on a session for Chess backing pianist Eddie Ware, and occasionally on early sessions with Muddy Waters.
Jacobs' own career took off when he recorded as a bandleader for Chess' subsidiary label Checker Records in 1952; the first completed take of the first song attempted at his very first session was massive hit, spending eight weeks in the #1 position on the
Billboard magazine R&B charts - the song was "
Juke", and it was the first harmonica instrumental ever to become a hit on the
R&B charts. (Three other harmonica instrumentals by Little Walter also reached the Billboard R&B top 10: "Off the Wall" reached #8, "Roller Coaster" achieved #6, and "Sad Hours" reached the #2 position while Juke was still on the charts.) "Juke" was the biggest hit to date for Chess and its affiliated labels, and secured Walter's position on the Chess artist roster for the next decade. Little Walter scored an impressive fourteen top-ten hits on the
R&B charts between 1952 and 1958, including two #1 hits (the second being "My Babe" in 1955), a feat never achieved by his former boss Muddy, nor by his fellow Chess blues artists
Howling Wolf and Rice "
Sonny Boy Willimason" Miller. A lot of these Little Walter's numbers were originals which he or Chess A&R man
Willie Dixon wrote. In general his sound was more modern and uptempo than the popular Chicago blues of the day, with a jazzier feel than other contemporary blues harmonica players.
Jacobs frequently appeared as a harmonica sideman behind others in the Chess stable of artists, including
Jimmy Rogers, John Brim, Rocky Fuller (aka
Louisiana Red/Iverson Minter),
Memphis Minnie, The Coronets,
Johnny Shines, Floyd Jones, and
Bo Diddley, and
Shel Silverstein, and on other record labels backing
Otis Rush, Johnny Young, and
Robert Nighthawk.