As Milton grew into a young man, he didn't waste any time learning the ropes or absorbing all the musical possibilities that existed at the time. He played street corners, alleys, dives, you name it, carefully developing his craft and attracting the attention of established acts and local record labels. By the time Ike Turner introduced Milton to Sam Phillips of Sun Records in the early 50's, he was a young but seasoned performer with a momentous live show that created a buzz in every town he played. His debut single Beggin My Baby  was recorded and released at the same time Sam Phillips was molding the sound of another unknown talent from Mississippi: Elvis Presley.  

After recording a series of sides at Sun without great fanfare, Milton moved to East St. Louis’ Bobbin Records, where his recording career flourished. He also became Bobbin's A&R chief and working partner to its owner, Bob Lyons. During this era, Milton signed such artists as Albert King and Fontella Bass to the label. Most importantly, he cut his own first hit, I'm A Lonely Man, in 1958.  

Milton's skyrocketing success soon drew the attention of Chess Records executives in Chicago, who signed him to Chess Checkers label and moved him north. Chess carried Little Milton from southern blues circuit fame to the national spotlight and to white audiences. Milton's recordings realized only moderate chart success, until he cut We're Gonna Make It, which hit No. 1 on Billboard magazines R&B singles chart in 1965. On the Checker label, he registered hits from 1962 through 1971 that would become American blues classics and staples of his live shows. His Checker recordings included Baby I Love You, If Walls Could Talk, Feel So Bad, Who's Cheating Who? and the unforgettable Grits Ain't Groceries. After the death of label founder Leonard Chess in 1969, the company eventually dissolved and Milton signed with Stax.

At Stax, he joined a virtual who’s who of influential black recording artist of the day including Isaac Hayes, Rufus & Carla Thomas, Booker T. & The M.G.'s, Albert King and, coincidentally, another future Malaco star, the late Johnnie Taylor. Milton’s legend only grew at Stax, where from 1971 through 1975, he stacked up more mega hits…including Walking The Back Streets and Cryin and That's What Love Will Make You Do. 

When Stax filed bankruptcy in 1975, Milton joined TK/Glades Records in Miami, then home to such artist as Betty Wright, K. C. & The Sunshine Band and Latimore. There, he racked up another charted hit, Friend of Mine. But the Glade label also went out of business.  Consequently, in 1983, he released his only album for MCA, Age Ain't Nothin But A Number. The title cut was an instant-charted hit.

In 1984, Little Milton united with Malaco Records and began the longest professional association of his career. He continued his exceptional vocal and guitar styles and quickly became one of Malaco's biggest selling artists. He swept up such honors as the 1988 W. C. Handy Blues Entertainer of the Year Award and the 2000 Grammy award nomination. He also was inducted into the Blues Hall of Fame.

Over the years, Malaco has released 14 of Little Milton's albums, including the critically acclaimed, Billboard blues smash hit Cheatin Habit. Cheatin Habit followed his wildly successful Little Milton's Greatest Hits compilation.  Some of Little Milton's Malaco cuts that have become American blues standards include Annie Mae's Cafe, The Blues is Alright, Little Bluebird, Room 244, I Was Trying Not to Break Down, Catch You on Your Way Down, Murder on Your Hands, and Comeback Kind of Love.

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