In August 2016, Douglas Mcgowan arrived at a modest brick house near central Nashville with a contract and the faint hope of a face-to-face meeting with the home’s mysterious occupant.

Mr. Mcgowan, a scout for the archival record label the Numero Group, was looking for Jackie Shane, a venerated but misunderstood soul singer who had not been seen in public in nearly five decades. He had obtained Ms. Shane’s phone number three years earlier through a friend of hers, and the pair had developed what felt like a genuine long distance friendship — he engaged her on current affairs over lengthy, discursive phone calls and steered clear of prying personal questions; she teased him with a nickname, “Hot lips,” and told him he sounded short.

At Ms. Shane’s house in Nashville, Mr. Mcgowan had envisioned a climactic rendezvous. But it never happened.

“I’m not ready,” Mr. Mcgowan said Ms. Shane called out from the other side of a wall. After two hours of debating in the summer heat, he finally gave up, leaving the contract — an agreement for Ms. Shane to work with the Numero Group to reissue her catalog — on her front doorstep.