The Story of John Henry — which came in the form of two 10-inch , 33 1/3 RPM vinyl records — was a big success and led to Josh White making more albums for Elektra. A lot of them featured re-recordings of his old songs, which had previously been released on shellac 78s that were now obsolete. As with the CD boom of the 1990s, a new medium is good for business.

The medieval English ballads were left behind on favor of a steady diet of folky blues and bluesy folk. This made the records easier to market, and reflected White’s general mid-career shift into something of a nostalgia act. The folk and blues revival that would come to full flower in the late 1950s and early 1960s was already underway, and provided a reliable stream of educated customers with spending money.

Some of the material seems intended to position him as a sort of blues/folk Frank Sinatra, not entirely without success:

Even so, it took a while for him to climb back to solvency. Apparently he had a network of women he could fall back on when things got rough; according to one lady friend,

A great many of the women that he was with had money, and that was his purpose. I’m being blunt about this, but he would by the first to tell you. He’d say to me, “I have to spend some time with so-and-so,” and suddenly he would have money again to take care of everything. It sounds brutal, but it’s true. He did what he had to do to survive.

His career was generally on the upswing throughout the late 50s, recording for Elektra and other labels both domestically and abroad, playing at colleges and music festivals, and doing long residencies at clubs in England, Sweden, New York, Chicago, and San Francisco. They loved him in S.F., according to Enrico Balducci, owner of the hungry i:

He’d call me and say, ‘Listen, I want to spend a little time in Frisco; can I stay a month?’ And I’d say, ‘When do you want to come?’ So he’d give me his date and we’d make it up. He would stay for as long as he wanted to stay — a month, two months. All the liberals in San Francisco would be there, and there were quite a few of them. There’s 450 seats in that room, and they used to fill it. The Gateway Singers would probably open the show, and then Mort Sahl would be in the middle, and then Josh would close it.

White also began to dabble in the developing medium of television. Society Blues contains a wonderful description of his appearance on a show called — I shit you not — Playboy’s Penthouse. I haven’t been able to find any video, so you’ll have to use your imagination here. You might want to wait until after dark; fix yourself something to drink and/or smoke, and let your mind drift away. The place is Chicago, the time is March 1960, and away we go:

In a penthouse high above the city, Hugh Hefner is hosting an array of well-dressed guests. Various performers are singled out to do their shtick — including a young Bob Newhart — but none seems as relaxed as Josh. He appears in uncharacteristically formal evening dress, but during the second song, “Nobody Knows You When You’re Down and Out,” he decides to get comfortable. Over the course of the first verse, without ever pausing in his performance, he manages to remove his watch and tie and to unbutton his shirt collar. Then he swings into “Jelly Jelly.” As Hefner nods in time, he teases the lyric, then brings his left hand up over the guitar neck and fires off a set of electrifying bass slides, played with the side of his thumb, before sinuously wrapping his hand around the neck for a sexy finish.