FEEL THE PILLOW WHERE YOUR BABY USED TO LAY: We woke up one morning and found Ray Charles was gone. He was a titan of American music, a true pioneer, blazing through boundaries among styles and genres, redrawing the map for the artists who followed him.

His music married emotional abandon with precision, an honest and searching heart with soaring ambition and a formidable will. In the studio and in his career moves, Brother Ray knew what he wanted and generally got his way. He held the upper hand in most of his relationships: with women, with fellow musicians, with business managers and record labels. He lived life on his terms.

He had a sappy side—one has to admit this about an artist who recorded a version of “My Bonnie Lies Over the Ocean.” But many of Charles’s best songs are bracingly unsentimental and concrete. The lyrics are about love won and lost, of course, but also about work, and about money (“Busted,” “Greenbacks,” “Blackjack”), and the interrelatedness of these elements. Love is not mystical or magical, it simply offers shelter against life’s hardships. Doing right by your mate means making her comfortable. You got no money, you just ain’t no good, complains Margie Hendrix of the Raelettes. Love is a bargain; it’s not a job for Cupid’s arrow; it’s a matter for negotiation and give and take. Come back, baby / Let’s talk it over one more time.

Charles sometimes confounded the expectations of liberal whites and movement blacks in the ‘60s and ‘70s, avoiding bold statements about race, choosing the “wrong” anthems to sing, “America the Beautiful” instead of “We Shall Overcome” (not to denigrate his powerful rendering of “America the Beautiful”). His perspective was well-earned, as a black man raised in the Jim Crow South who fled its regime at a young age. And taking a contrarian stance was perfectly in character for Charles. But he was not immune to black political yearnings, merely attuned to the downside risk, the threat of a white backlash obliterating black gains. The advance of freedom is not inevitable, nor orderly. This sense of forboding permeates Charles’s 1961 recording of the Percy Mayfield composition “The Danger Zone.” He sounds a note poised between hope and worry:

My love for the world is like always
For the world is a part of me
That’s why I’m so afraid of the progress that’s been made
Toward eternity

Charles hit his stride in 1954, the year of Elvis Presley and Sun Records, and Brown v. Board of Ed., and Willie Mays’s great catch in the Polo Grounds. In a couple of hastily arranged recording sessions squeezed into his tour schedule—one in Atlanta, one in Miami—Charles recorded a series of songs, his own compositions, that flirt with sappiness, but transcend it on the strength of intensity, suppleness, and skill. This is my favorite “moment” in his career. In these songs Charles’s singing is a wonder; every whine and crack in his voice is purposeful. His band operates like a fine-tuned luxury automobile, supplying propulsion and grace in whatever combination the song needs. “Come Back Baby” is fascinating for its shift in tone and address: the singer first pleads to his lover, then preaches to his listeners about all he would do to win her back, then in the end speaks to the woman defiantly, warning her not to take him for granted. “I Got a Woman” clips along joyfully—the luxury car is at highway cruising speed here—as Charles alternates stanzas of praise and gratitude with sly, confidential boasts about how good he has it at home.

The down-tempo number “A Fool for You” conjures up a slow solitary walk, and a man’s imaginary conversation with the object of his heartache. She has broken it off, she has a new man, but he can’t accept his fate. The band shifts gears; the cadence is more urgent. Another shift in address as the singer seeks communion with his audience: Did you ever wake up in the morning / Just about the break of day / Reach over and feel the pillow / Where your baby used to lay. It’s a universal lament. We seem to be witnessing a slow-motion nervous breakdown. In the end we’re left with a simple yet unanswerable question: I want to know what makes me be a fool for you.