When Otis Redding recorded “Sittin’ on the dock of a bay” — a quiet, vulnerable departure from his signature power vocal style — he wasn’t sure whether it would help cement his place at the top of the charts, or, weigh down his steady rise to stardom.

The 26-year-old from Macon, Georgia would never find out. Three days after the 1967 recording, Redding died in a plane crash. Yet the song, a careful blend of folk and soul, made his voice more popular than any track before it. It was the first posthumous single to top the charts in the U.S., and would go on to be covered by dozens of musicians in the decades that followed.

To understand the song, though, you have to understand how Redding — who could neither read nor write music — created a sound that, years after his death, would continue to shape Southern soul, Mark Ribowsky writes in his new book.

As Ribowsky takes us back to Redding’s rise as a teenage star and his shortlived, but successful, career, dive into early soul with this playlist of his greatest hits.

Want more? Listen to our full hour on Otis Redding.