By 1959, while unable to get another record deal, Milton set up his own label in St. Louis: Bobbin Records. During this time, he secured a distribution deal with the Chess Brothers. Within two years, his singles were appearing on the Checker imprint.
Finally, after eight releases on Checker, Milton scored the biggest hit of his career: “We’re Gonna Make It.” This 1965 recording, that echoed sentiments shared with the Civil Rights movement, charted at #1 on the R&B charts, and it was Little Milton’s only single to chart in the Top 40; it peaked at #25.
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