That year of 1976-77 was a hard time in Dave Van Ronk’s life. The sixties were over and he’d had some good times but hadn’t caught the brass ring. He’d done a half-dozen albums for major labels — two for Mercury, two for Verve, one for Polydor, one for Cadet — all putting decent money behind him and hoping for at least a modest hit, but the last of those had been in 1973 and now he was with Philo, a small Vermont folk label, and although he was proud of the music he was making, it was clear he wasn’t going to get out of his one-bedroom apartment with its windows on an airshaft, and not entirely clear how he’d manage the rent on that.

He was also overweight and drinking a lot of whiskey, and by the second bottle he had a tendency to get depressed and angry. As I recall, it was in one of those moods that he first played me Don Schlitz’s demo cassette of “The Gambler.” He’d heard the song, picked it for a hit, and asked for a recording hold on it — the right to do the first record of it, or at least the first single. But he hadn’t been able to get anyone interested. Philo didn’t do singles, and the majors had written him off as a has-been or almost-was.

Honestly, I couldn’t blame them: it wasn’t the kind of song I associated with Dave and I forgot about it until he reminded me a couple of years later, after Kenny Rogers sold a gazillion records with it.

It still wasn’t the kind of song I associated with Dave, but that was about me, not him. I preferred him with just a guitar and wasn’t wild about his more ambitiously orchestrated recordings, and a lot of his other fans agreed with me, and that was why I was still coming around and he was stuck in that tiny apartment.

Herewith I must interject a story that includes some raw language:

One of the first times I met Dave, he was playing at Passim Coffeehouse, and during the break a reporter from the BBC asked for an interview. We went to the quiet bar at the nearby Chinese restaurant, and everything was going fine until the reporter said, “Dave, one thing I’ve always admired about you is that you never sold out.”

There was a long pause, and then Dave leaned into the mike and growled, “Listen: I’ve been standing on 42nd Street for twenty years, bent over with my pants around my ankles… it’s just that nobody’s fucked me.”

He knew how the business worked, and was sure with the right song and the right production and the right promotion from the right record company he could get a hit — and it hadn’t happened. He’d tried forming a rock band; he’d tried recording with strings. He had ideas about what he did best and what music he preferred, but also saw himself as a craftsman and a professional who could have more than held his own with Kenny Rogers.

Maybe he was right and if all the pieces had come together, “The Gambler” could have done it for him. He certainly had the requisite world-weariness, and was a good actor and terrific storyteller, and I can imagine his gruff whisper being perfect for this role.

The reasonably happy ending to that story is that he eventually pulled himself together, lost the weight, switched to wine, got some European and Japanese tours, managed to keep paying the rent, made a lot of fine music, lived another 25 years, and hosted many more long evenings of great conversation with good friends. He never got a hit, never got out of that apartment, but he settled into being the eminence grise of the Village folk scene and made the best of it. Like the man said: “Every hand’s a winner, just like every hand’s a loser.”