Bootleg Betty
Why Dylan Chose Midler For “Buckets Of Rain” Duet?
By Mister D
May 16, 2026
Dylan chose Bette Midler because, in late 1975, they were orbiting the same creative scene, sparking off each other in New York clubs, and genuinely enjoying an unexpected artistic chemistry. The surviving reporting doesn’t give a single, definitive “Bob said X” explanation, but the available sources paint a clear picture of why the collaboration happened and why it made sense to him at that moment.
The clearest reasons supported by sources
- They were suddenly spending time together in the same rooms
Rolling Stone notes that in fall 1975, Dylan had just moved back to New York and was hanging out constantly at the Other End (formerly the Bitter End), where Bob Neuwirth was performing. Midler was part of that same circle, dropping in and even joining Neuwirth onstage. This put Dylan and Midler in repeated, casual proximity. - They bonded during a run of club nights and parties
Both were present at Mike Porco’s 61st?birthday celebration at Gerde’s Folk City—an event packed with Rolling Thunder Revue regulars. Midler performed “Friends,” and Dylan was part of the same loose, celebratory atmosphere. This was the same week they ended up in the studio together. - They were already in the same studio—literally
Midler was recording Songs for the New Depression at Secret Sound, Todd Rundgren’s loft studio. Dylan showed up there during the same week, and the two ended up recording “Buckets of Rain” together. Bootlegs confirm that the session was spontaneous, playful, and full of improvisation. - Dylan was in an experimental, open, playful phase
Far Out Magazine describes Dylan in this period as treating songs as fluid, malleable things—happy to reshape them, try new approaches, and collaborate unexpectedly. His willingness to “play around with it” made him open to a duet that would have seemed unlikely on paper.
What this means in practice
Put together, the evidence suggests:
It wasn’t a calculated career move—it was a vibe.
Dylan liked Midler, liked her energy, and liked the looseness of the sessions happening around Neuwirth and the Village clubs.
He was creatively charged after Blood on the Tracks and before the full Rolling Thunder Revue momentum hit.
Midler was fearless, funny, and musically adventurous, which fit Dylan’s mood at the time.
The duet feels like two artists who surprised themselves by clicking.
The non-obvious layer
The Rolling Stone piece emphasizes how unlikely the pairing seemed—“different galaxies,” it says—but that’s exactly why Dylan leaned in. He has always gravitated toward artists who disrupt expectations. Midler’s theatricality, humor, and emotional directness offered him a foil he didn’t usually get.
Their “Buckets of Rain” isn’t just a duet—it’s a document of two very different performers discovering a shared groove in real time.
Sources: Rolling Stone Magazine and Far Out Magazine
