A New Madonna Book Features Fresh Details About Sean Penn Romance, Ken Regan Photos, Interviews With Nile Rodgers and More

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Madonna’s 1985 ascent is getting a new close-up.

Insight Editions is set to release “Madonna: Into the Groove: An Intimate Portrait of the Queen of Pop,” a new photo book built around the work of photographer Ken Regan, with text by Tomás Mier. The book focuses on a pivotal year in Madonna’s career, when “Like a Virgin,” “Material Girl,” “Desperately Seeking Susan,” the Virgin Tour and Live Aid helped turn her from rising pop star into global phenomenon.

The book includes intimate and archival images from Regan’s 1985 sessions with Madonna, including shoots at Le Mondrian in Los Angeles, where she posed in a hotel room, ballroom and gym. The interiors show Madonna in several mid-’80s looks: lace leggings, leotards, crucifixes, stacked bracelets, “Healthy Swimmer” styling and the punk-Catholic iconography that became central to her early image.

Structured in chapters including “A Material Girl,” “Le Mondrian,” “The Virgin Tour,” “Live Aid” and “Aftermath,” the book combines glossy studio-style photography with behind-the-scenes stories from collaborators, including Nile Rodgers, Maripol and members of Regan’s circle. It also places Madonna’s rise against the broader cultural landscape of 1985, from MTV’s growing power to the backlash against sexually provocative pop music.

One of the book’s most striking sections centers on Live Aid, where Regan served as the official photographer for the Philadelphia half of the benefit concert. A screenshot from the book, shared exclusively with Variety, details how Regan was attempting to capture as many major stars as possible backstage and onstage, from Bob Dylan and Tina Turner to Keith Richards, Mick Jagger and Madonna.

According to the excerpt, Regan had originally planned a controlled photo setup near the stage entrance, complete with lights and a generator. But once the concert began, the plan collapsed: the generator failed, the backstage area became chaotic and Regan had to improvise with multiple cameras and a flash. He ultimately captured a rare group photo featuring several of the day’s biggest names — including Madonna and Dylan — in only a handful of frames.

The excerpt also recounts a tense, previously untold moment involving Sean Penn, who had recently reconnected with Madonna and would marry her the following month. Regan’s assistant Craig Blankenhorn remembers Penn approaching him and asking why Regan had sold photos of Madonna to Penthouse. Blankenhorn says Regan explained that he did not know the backstory of how the photos would be published and had not intended to embarrass Madonna. The conversation escalated, with Blankenhorn recalling that Penn spat on his shoes before the moment ended without going further.

The story captures the the volatile beginnings of one of the decade’s most high-profile celebrity relationships. Two days after Live Aid, Sire released “Into the Groove” as a U.K. single, where it went to No. 1. Weeks later, Madonna married Penn in Malibu, at a heavily covered wedding attended by stars including Cher, Tom Cruise, Carrie Fisher, Keith Haring, Diane Keaton, Rob Lowe, Martin Sheen, Christopher Walken and Andy Warhol.

The book follows the pop star’s 15th album “Confessions: II,” which Variety music writer Steven Horowitz calls “her best album in decades.”

Pre-order “Madonna: Into the Groove” online here.