• Michele Singer Reiner captured famous 1987 image for “The Art of the Deal”
• Director husband Rob Reiner recounted Trump’s hairspray obsession during rooftop shoot
• Cover photo helped solidify Trump’s image as successful tycoon for decades

LOS ANGELES, CA (TDR) — An unexpected professional connection between Michele Singer Reiner and President Donald Trump has resurfaced following the photographer’s death alongside her husband, acclaimed director Rob Reiner, on Sunday. Singer Reiner captured the iconic cover image for Trump’s 1987 bestseller “The Art of the Deal,” a photograph that shaped his public persona for decades.

High-Rise Photo Shoot Above Manhattan

The legendary image was photographed at a construction site overlooking Central Park, deliberately chosen to convey grandeur and authority. Rob Reiner shared details about the shoot during a 2017 appearance on Politico’s “Off Message” podcast, recounting stories his wife told him about working with Trump that day.

“My wife, Michele, who is a professional photographer, she took the photo that’s on the cover of the book ‘The Art of the Deal.'”

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The director described how Michele witnessed Trump’s meticulous attention to appearance when wind began whipping across the rooftop. According to Rob’s retelling, Trump insisted he needed special hairspray to protect his signature hairstyle during the outdoor session.

Image That Built a Brand

Peter Osnos, the original publisher of “The Art of the Deal,” confirmed Monday that Michele Singer photographed the cover image that would become synonymous with Trump’s business empire. The book reportedly sold 1.1 million copies by 2016, with Michele’s photograph amplifying the prose that established Trump as the emblem of the successful tycoon.

In the 2017 podcast interview, Rob Reiner acknowledged Trump’s charismatic presence, noting his wife captured someone who was “always larger than life” and possessed natural magnetism. The director conceded Trump could be effective as a politician performing before certain audiences, though he added it did not resonate with everyone.

Career Beyond One Famous Shot

Before meeting Rob Reiner on the set of “When Harry Met Sally” in 1989, Michele Singer worked as a professional photographer whose images appeared in major publications. Her portfolio included work on MysteryDisc video games and various editorial assignments throughout the 1980s.

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Singer Reiner later transitioned into producing, earning credits on several of her husband’s projects including an Emmy nomination for the documentary “Albert Brooks: Defending My Life”. She also produced “God & Country,” a documentary examining Christian nationalism in America.

Ironic Political Divide

The professional connection between Michele Singer Reiner and Trump stands in stark contrast to the political relationship that developed between Trump and Rob Reiner over subsequent decades. The director became one of Hollywood’s most outspoken Trump critics, calling him “mentally unfit” for the presidency in a 2017 Variety interview.

In a 2018 Guardian interview, Rob jokingly reflected on his wife’s role creating the famous book cover, quipping that Michele had “a lot to atone for” given how significantly it boosted Trump’s brand recognition and public profile.

The couple met while Rob was directing “When Harry Met Sally,” with their romance inspiring him to change the film’s ending so the titular characters would end up together. They married in 1989 and shared three children together over 36 years of marriage.

Will the iconic photograph Michele Singer captured in 1987 remain her most enduring professional legacy despite her accomplished career in photography and film production?

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