Dangerous Minds
Inside Bob Dylan and Bette Midler’s wonderfully awkward 1975 recording session
By Richard Metzger
July 30, 2026
I have a confession. I can happily listen to half an hour of musicians tuning guitars, chatting nonsense and trying to remember lyrics if somebody forgot to switch the tape recorder off.
Seriously.
Some of my favourite bootlegs aren’t the ones with the unreleased songs. They’re the ones where you hear Bob Dylan mumbling to somebody across the room, Keith Richards asking what key they’re in, or John Lennon making a joke that nobody outside the studio was ever supposed to hear. Those little moments make famous people seem human again. That’s exactly why this recording is such a treat.
In October 1975, Bob Dylan dropped into the studio with Bette Midler to record a duet on ‘Buckets of Rain’ for her Songs for the New Depression album. The finished version is lovely enough, but that’s not the reason people still talk about the session. Years later, almost 27 minutes of tape from that afternoon began circulating among Dylan collectors as part of Bob Dylan New York Sessions 1974-1975, and it’s one of those rare recordings that lets you feel like you’ve quietly wandered into the room while history’s happening.
According to the original bootleg notes:
“It opens with some upgrades of the original Blood on the Tracks sessions from September 1974, and progresses chronologically through some early Desire sessions, winding up to the main event: almost half an hour of never-heard October 1975 session outtakes of the recording of Bette Midler’s cover of ‘Buckets of Rain’ with Dylan, which would show up on her Songs for the New Depression album the following January.”
October 1975 wasn’t exactly a quiet spell for Dylan. Blood on the Tracks had come out earlier that year, Desire was starting to take shape and the Rolling Thunder Revue was only weeks away from setting off across America. Somehow, in the middle of all that chaos, he found time to record with Midler. Apparently he enjoyed the experience enough that he wanted her to join Rolling Thunder as well, and honestly, she’d probably have slotted into that wonderfully unruly travelling circus without anybody batting an eyelid.
The tape itself isn’t dramatic. Nobody storms out. Nobody smashes a guitar. That’s what makes it so enjoyable. It’s just people making a record.
Midler worries over one particular lyric, though, admitting, “I can’t sing ‘I ain’t no monkey’”, but Dylan doesn’t laugh or tease her, and just nudges her along until she gives it a go. It’s such a small exchange you’d never think twice about it, but those are exactly the moments that disappear once an album has been polished, mixed and released.
Moogy Klingman is at the piano throughout, keeping everything gently ticking over, and before long the session wanders off in an entirely different direction. Dylan suddenly launches into Smokey Robinson and The Miracles’ ‘You Really Got a Hold on Me’, singing with far more gusto than you’d probably expect from an informal rehearsal, while Midler happily joins in.
Then, because musicians love gossip almost as much as they love making music, the conversation takes another turn.
Midler mentions Paul Simon, sounding more than a little irritated that he refuses to speak to her.
“This’ll show him!”
A few minutes later Patti Smith catches a stray bullet too.
“At least I can sing in tune!”
That line sent me down a rabbit hole because I’d completely forgotten about the long-running friction between the two women. Patti later told Barry Miles that Midler once threw a beer in her face during a Dylan-related gathering in New York around the same time. Whether that was professional rivalry, personality clashes or something a little more romantic is anyone’s guess. Midler would later admit she’d got to “first base” with Dylan in the back of his Cadillac, so you can draw your own conclusions. Dylan had a habit of collecting fascinating people around him in the mid-70s, and every now and then those personalities inevitably collided.
Nobody’s claiming these recordings belong alongside Highway 61 Revisited or Blood on the Tracks, and that’s the real attraction: getting to spend half an hour in the company of Dylan and Midler before anybody remembers there’s an audience waiting outside. They’re trying ideas, joking around, drifting into old soul songs, chatting about other musicians and generally behaving like people who have no idea somebody will still be listening 50 years later.
So if you’ve ever wondered what it might have been like to pull up a chair in the corner of a New York recording studio while Bob Dylan and Bette Midler made a record together, this bootleg is about as close as you’re ever going to get.
And, personally, I’ll take 27 minutes of this over another slickly narrated rock documentary any day.
