Insight Editions is set to release a new Madonna photo book built around Ken Regan’s 1985 pictures, and it adds fresh material to a year that turned her rise into something much bigger. Madonna: Into the Groove: An Intimate Portrait of the Queen of Pop is written by Tomás Mier and centers on the stretch when Like a Virgin, Material Girl, Desperately Seeking Susan, the Virgin Tour and Live Aid were all pushing her into the spotlight at once.
That is why the book is landing now. Readers looking for Rolling Stone-era Madonna material are getting a package that moves from performance to image-making to the machinery around her fame, with intimate and archival photographs from Regan’s 1985 sessions and recollections from collaborators including Nile Rodgers, Maripol and members of Regan’s circle. The book is arranged in chapters titled A Material Girl, Le Mondrian, The Virgin Tour, Live Aid and Aftermath, which gives the story a clear arc from breakout to aftermath.
The images themselves aim at the Madonna people remember: her at Le Mondrian in Los Angeles, in a hotel room, ballroom and gym, dressed in lace leggings, leotards, crucifixes, stacked bracelets and the kind of Healthy Swimmer styling that captured mid-’80s pop confidence without looking staged to the bone. The book also places that rise against MTV’s expanding reach and the backlash aimed at sexually provocative pop music, which helps explain why her image mattered as much as her songs.
But the book does not stay in the glossy lane. Craig Blankenhorn recalled Sean Penn asking why Regan had sold photos of Madonna to Penthouse, and he said Regan answered that he did not know how the photos would be published and had not meant to embarrass Madonna. Blankenhorn said Penn then spat on his shoes before the exchange ended. That episode sits inside a book that also treats the early relationship as part of Madonna’s ascent, a reminder that the same year that built the star also carried its own ugly offstage collisions.
Regan’s Live Aid work adds another layer. He was the official photographer for the Philadelphia half of the event and tried to shoot major names backstage and onstage, including Bob Dylan, Tina Turner, Keith Richards, Mick Jagger and Madonna. A planned setup near the stage entrance fell apart when the generator failed after the concert began, so he improvised with multiple cameras and a flash. In only a handful of frames, he captured a rare group photo that included several of those names, one more sign that the book is not just a gallery but a record of how closely fame, timing and accident were tied together in 1985.
The timing of that year still matters because the momentum kept building. Two days after Live Aid, Sire released Into the Groove as a U.K. single, and it went to No. 1. Weeks later, Madonna married Sean Penn in Malibu, in a ceremony heavily covered and attended by Cher, Tom Cruise, Carrie Fisher, Keith Haring, Diane Keaton, Rob Lowe, Martin Sheen, Christopher Walken and Andy Warhol. The book’s unresolved question is not whether 1985 mattered; it is how much of Madonna’s myth was already being made in public, and how much of it was being fought over in private.
