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David LaChapelle in T, The New York Times Style Magazine

The American photographer David LaChapelle, 63, redefined the celebrity portrait, shooting entertainers and world leaders ranging from Lil’ Kim to Hillary Clinton on surreal, cinematic sets that often blend religious iconography with Baroque or Renaissance motifs. In 1996, New York magazine called him “the Fellini of Photography.” LaChapelle came of age in 1980s Manhattan, starting out as a photographer for Interview magazine before shooting for Vanity Fair and Rolling Stone. One of his most unforgettable images is from a 1996 commission for Details magazine featuring the American rapper Tupac Shakur, then 24. “Solitary II,” as the image is titled, features the hip-hop star — who’d recently been released after serving a prison sentence for sexual abuse — adorned with heavy gold jewelry, a “Thug Life” tattoo across his abdomen, reclining in a bathtub. The image could be read as suggesting that the arts-school-educated Shakur (he majored in theater) was washing away his violent past in preparation for a creative rebirth. Instead, five months later, he was killed in a drive-by shooting in Las Vegas. — K.W.

Ian Bradley: This Tupac series represents hip-hop moving into the world of luxury fashion. He walked in a Romeo Gigli men’s wear show shortly after this. It was right before his death; his security guards walked the runway too.

Nick Haramis: At this point, mainstream rap was still largely homophobic. But with this image, LaChapelle almost seems to be encouraging Tupac to embrace a certain kind of queerness, or softness at least.

Ian Bradley: Yeah, he’s playing that up. Tupac got a lot of flak for this.

Inez Van Lamsweerde: It’s fabulous.

Choosing the 25 most influential fashion photographs of the past century is an impossible task. Partly, that’s because influence is hard to trace. Without knowing firsthand, one can’t really say whether Marc Jacobs’s 1993 grunge collection (the one that got him fired from Perry Ellis) was inspired by the work of Joseph Szabo, whose photographs in the 1970s captured the angst and glory of suburban adolescence; or whether today’s street-style photographers admire or even know about the midcentury American photographer Saul Leiter. There’s also the fact that some fine-art photographers have had a great deal of influence on fashion, even though they aren’t considered fashion photographers and wouldn’t refer to themselves as such. In general, fashion photography was defined broadly enough here to include the work of fine artists, street-style photographers, backstage and nightlife photographers and paparazzi. And it didn’t matter if an image was meant as a fashion photograph, so long as the picture later inspired a designer, collection, or trend, or it changed how we might think about style.

One morning this past July, a group of experts convened at the Times building in Midtown Manhattan to debate and make the list below. Huddled in a conference room for nearly three hours, six image makers — the New York-based stylist and T contributor Ian Bradley; the Canadian model Linda Evangelista, one of the original “supers” in the late 1980s and ’90s; the American fashion designer and Khaite founder, Cate Holstein; the Dutch American photography duo Inez van Lamsweerde and Vinoodh Matadin; and T’s creative director, Patrick Li — considered the merits of about 60 pictures they’d nominated, spanning roughly 100 years. 

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