Back when Jason Isbell was drinking, he spent a lot of his New York City downtime at the Lakeside Lounge, on Avenue B. “It’s gone now,” Isbell, an Alabama-born singer-songwriter, said on a recent visit to the city. “I spent every hour I wasn’t working in that place getting fucked up.” Sometimes when he was working he’d get fucked up, too. He recalled a disastrous show at Webster Hall, when, after hitting the vodka backstage (“Rednecks can’t drink clear liquor”), he got into a fight with his bass player—who happened to be his wife at the time—and she ended up hurting her hand and had to perform with a bandage. “So much misery there,” he said.

Now when Isbell, who is thirty-six, has time off in the city, he wanders. He and his manager, Traci Thomas, were on their way to the Brooklyn Museum, to see “Basquiat: The Unknown Notebooks.” Isbell was wearing a stiff denim jacket and had a couple of heavy silver rings on his fingers. His hair was slicked back, like a fifth-grade boy getting his school picture taken.

Isbell, the former guitarist with Drive-By Truckers, quit drinking three and a half years ago. After getting sober, he recorded an acclaimed solo album, “Southeastern” (2013); his new release, “Something More Than Free,” continues the character-driven story-song vein. He and his wife, Amanda Shires, whose fiddle and vocal harmonies are heard on much of the new album, are expecting their first child in early September.

To get to the Basquiat exhibition, Isbell and Thomas passed through the Decorative Arts Gallery’s period rooms, including one from a South Carolina plantation house. “The Iodine State!” Isbell exclaimed, walking around the dining-room table. Is it a burden for a songwriter with progressive values to represent the South in his music? “It might be a burden, but it’s also a blessing,” Isbell replied. “What would I have to write about if I were from Vermont?”

Leaving the Old South behind, the pair wandered on to “Unknown Notebooks,” which has a decidedly more urban vibe. The show depicts Jean-Michel Basquiat the writer—the late-night coke-crazed genius of visual jazz. Interspersed with the notebook pages are painted canvases covered with dense archipelagoes of words. Basquiat’s former girlfriend Suzanne Mallouk, in Jennifer Clement’s “Widow Basquiat,” recalls nights in the artist’s downtown loft, getting high and reading out medical terms from “Gray’s Anatomy” as Jean-Michel painted on whatever surfaces he could find. Then they’d go score more drugs.

Isbell, who did his share of coke back in the day, could only shake his head over Basquiat’s fate. He said he felt lucky to be a songwriter, because it was a learned craft that is not helped by alcohol and drugs, “except for caffeine.” He added, “Another difference is, with a song, you know when it’s done. How do you know when that is finished?”—he gestured toward “Tuxedo,” a black silk-screen festooned with blocks of words.

They kept moving. “He wrote the way people text now,” Isbell observed, squinting at another densely word-filled work. Other lines sounded like lyrics. One notebook page read, “Nicotine Walks on Eggshells Medicated.”

“I know that feeling,” Isbell said.

In the later works, the feeling of doom becomes more insistent. The writing gets more manic, the lettering strung out, foretelling Basquiat’s bleak death of a heroin overdose at twenty-seven. He was found kneeling by a fan in his loft, as though trying to get some air.

On his way through the gift shop, Isbell said, “Got to get me a Basquiat hat! That’s a no-brainer, as far as I’m concerned.” He put down twenty-five dollars, pulled the hat over his slicked hair, and was off to another gig in another town. ♦