In the Seventies — or any other decade, in fact — it would have been hard to imagine less-likely duet partners than Bob Dylan and Bette Midler. In the fall of 1975, Dylan was newly invigorated, coming off Blood on the Tracks, and Midler was the midst of her first flush of pop fame, which had begun with her 1973 hit “Boogie Woogie Bugle Boy.” From their voices to their personas, they didn’t just seem to exist on separate planets but in different galaxies.

But in January 1976, 45 years ago this month, they joined together in song for the first and so far only time. That month, Midler released her third album, Songs for the New Depression, which included her rendition of Dylan’s “Buckets of Rain” — with the songwriter himself joining in.

The origins of their collaboration are vague, but in the fall of 1975, the two were clearly bonding. Having just moved back to New York, Dylan plunged back into the world of the Greenwich Village folk clubs that had nurtured him. In particular, he’d taken to hanging out at the Other End, the Bleecker Street venue that had once been known as the Bitter End. (The club eventually went back to its original name and survives to this day.) Dylan’s pal Bob Neuwirth was performing there, attracting everyone from Dylan to Midler to join him onstage.

One night that October, Dylan and what would be the core of his Rolling Thunder Revue converged at another iconic club, Gerde’s Folk City, to help owner Mike Porco celebrate his 61st birthday. Joan Baez, Eric Andersen, Patti Smith, David Blue, and Phil Ochs were in the house, along with Midler, who sang “Friends,” her unofficial theme song. (Scenes from that night were included in Martin Scorsese’s Rolling Thunder Revue: A Bob Dylan Story last year, and one of the fake characters, a Dutch filmmaker, was played by Midler’s husband Martin von Haselberg.) The same week as that party, Dylan and Midler found themselves at Secret Sound, a loft recording studio in Chelsea owned by Todd Rundgren; Midler was making her new album there, using members of Rundgren’s band.

Bootlegs of the session, which have circulated for some time, are among the most charming and oddball artifacts of either artist’s career. As producer and pianist Moogy Klingman repeatedly plays the chords of “Buckets of Rain,” the jaunty and somewhat lusty Blood on the Tracks song, Dylan and Midler exhibit a chummy, at times flirty, rapport. When they get to the line “Little red wagon/Little red bike/I ain’t no monkey, but I know what I like,” Midler joke-protests: “I can’t sing that line!”

“Let me hear you sing it — I’ll tell if you’re singing it or not,” Dylan commands, then laughs when she nails it. The two finally sing it together.

When Klingman brings up separating their voices on the track, Dylan declares, “We don’t want any separation on the voices,” and Midler shoots back with a sly, “Are you a one-take guy? … Ooh, I knew you were!” Dylan retorts, “Oh, I can last all night.” She tries to get him to take on Dobie Gray’s hit “Drift Away,” but the two instead end up playing around with a duet of Smokey Robinson’s “You’ve Really Got a Hold on Me” and taking a crack at Dylan’s “I Don’t Believe You (She Acts Like We Never Have Met).” At one point, Midler kids him with, “Goddamn it, I’ll turn you into Tony Bennett yet!”

At one point Dylan says, “You and Paul Simon shoulda done this one,” which leads Midler to explain that her planned duet with Simon on his “Gone at Last” had been scrapped. (Although she doesn’t mention the song by name, her voice was replaced with that of the late Phoebe Snow.) “He won’t speak with me anymore,” Midler says of Simon. “What’d you do to him?” Dylan replies, clearly looking for some tea. “I don’t know,” Midler says. “… He got pretty mad at me. I was pretty upset there for a while. … We cut a tune together and then he took my voice out. He was real mad. He was maaaad. This’ll show him.”

In its final version on Songs for the New Depression, “Buckets of Rain” is more fleshed out, with additional instrumentation (and Dylan’s voice ultimately higher in the mix). But the playfulness of those sessions remains. We can still hear Dylan crack up, and the song ends with Dylan’s line about her singing the song with Simon. No doubt Midler and Simon were more natural musical partners. But in retrospect, this rollicking, circus-soundtrack duet of “Buckets of Rain” was another early sign that Dylan would never be predictable.

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