Behind the Music: June Ambrose on Hip Hop’s Most Iconic ’90s Videos

With clients and collaborators like a young Jay Z and Missy Elliott, June Ambrose was responsible for styling many of the most iconic videos in ’90s hip-hop. Working with the director Hype Williams, rap’s own Edith Head dreamed up new characters and outfitted artists in exaggerated, influential styles that drew inspiration from across eras, social classes, cultures, and musical genres.

Though music videos of the period might be likened to short films in execution, their budgets approached the sums allotted to generously funded indie productions. Ambrose recalled making Busta Rhymes and Janet Jackson’s “What’s It Gonna Be?!” video for as much as $4 million. (For comparison, documents obtained by a Beyoncé fan site estimate the budget for Lemonade at $1.35 million—and that’s still a lot.)

“It was artist development,” she said. “It was character development.” Musicians like R. Kelly, Will Smith, and Missy Elliott inhabited new worlds and invented personae that could be cast off with their garments at the end of a shoot. Here’s the story behind some of the best looks of hip-hop’s music video heyday.

R. Kelly, “Half on a Baby,” 1998: Ambrose worked with R. Kelly for many years, though they parted ways “for my spirit and soul,” she said. “A lot of stuff that went on behind the scenes … I just couldn’t witness anymore.” But before it all fell apart, Ambrose styled some of Kelly’s most involved and iconic looks. For “Half on a Baby,” Kelly’s silk pajamas seemingly dissolve off his body about three-quarters of the way through the video. “When he’s walking up the steps,” Ambrose explained, “the suit is flying off his body, and I had like six assistants on the side pulling the strings.” It required about 15 takes to get it right — and 15 silk pajamas for Ambrose to sew.

Missy Elliott, “The Rain (Supa Dupa Fly), ” 1997: “In the treatment, [Hype] was like, ‘She’s a Michelin Man,'” Ambrose recalled — but she refused to dress Elliott in a white suit. “My whole thing was like, big glasses and shiny suits,” she said. Ambrose countered Williams’s proposal with an offer of patent leather and vinyl, but it was Williams who dug up the vintage Alain Mikli fire-flame glasses (“very rare, very expensive”) that complete the look. With Williams’s go-ahead, Ambrose designed the suit herself. But having never built an inflatable costume before, she found it kept deflating. It turned out there was a tiny leak that they hadn’t discovered till the team tried to inflate Elliott at a local gas station. “As we were walking back down the street to the set,” she said, “the suit is slowly, slowly, slowly deflating.” It worked to their advantage — Elliott needed a bit of room to dance, which would have been impossible if the suit were structurally sound, as intended. Ambrose ran out to grab a bicycle pump just before the shoot and worked with the choreographer to maneuver a quick air refill into the shot. “I’m behind the suit in the entire video pumping air back into it, per pop-lock,” she said. But as many times as you watch “The Rain (Supa Dupa Fly),” you won’t find Ambrose anywhere in sight.

Will Smith, “Gettin’ Jiggy With It,” 1997: Ambrose worked with Hype Williams yet again for Will Smith’s “Gettin’ Jiggy With It.” Their trademarks are both readily apparent, between Smith’s shiny bomber jacket and the distorted fish-eye camera angle. “Hype was constantly coming up with the most outrageous things,” Ambrose said. “I really give him a whole lot of credit for being the change agent at the time, because without those treatments, we really wouldn’t have had the script, in a sense, to do what we were doing — to tell the story.”

Foxy Brown and Jay-Z, “I’ll Be,” 1996: At the same time as Missy Elliott broke the mold for women in hip hop in the ’90s, Foxy Brown profited from the status quo. “That was her marketing strategy, talking about how ill her vagina was,” Ambrose said. “I was still trying to put her in a Norma Kamali one-strap dress, but it had to be super tight, and I was able to get it to the floor, but it had to be body con.” One of the resulting outfits in Brown’s Jay-Z collaboration “I’ll Be,” directed by Brett Ratner, does skim the floor as she raps “drippin’ Gabbana,” albeit with oblique-baring cutouts.

Jay-Z, “Feelin’ It,” 1997: Jay-Z’s “Feelin’ It” video was shot in Jamaica. Ambrose said she courted Armani to provide Jay-Z’s suits for the video, but as late as 1997 she still wasn’t able to recruit high-fashion designers to outfit her musicians. So she made the suit herself. “I wanted Armani first because I liked the softness of the shoulders,” she explained. “He wasn’t a suit guy, but I wanted him to feel like he was wearing a jogging suit while he was wearing his Armani suit.”

The Isley Brothers and R. Kelly, “Contagious,” 2001: In the videos for “Contagious,” by the Isley Brothers featuring R. Kelly, and for “Down Low (Nobody Has To Know)” by R. Kelly featuring the Isley Brothers, Ron Isley plays a fictional mob boss named Mr. Biggs. “Ron Isley’s no gangster,” Ambrose said. “It wasn’t always about gangsta music being real, but then you were storytelling and exaggerating certain things.” Rather than drawing from the gang culture of inner cities, Ambrose said she was inspired by “all of these great iconic movie references,” like Al Capone, the zoot suit, and the oversized gold medallion.

Puffy Daddy, Mase, and the Notorious B.I.G., “Mo Money Mo Problems,” 1998: The second single off B.I.G.’s album Life After Death, “Mo Money Mo Problems” was released posthumously. “We were burying gangsta music, in a sense,” Ambrose said. “B.I.G. had just died, and this album was, you know, we had collaborations with Sting. It was like the crossover of pop culture with hip hop, so it was slowly becoming hip-pop culture.” Puff Daddy and Mase were initially resistant to the shiny suits Ambrose conceived for the video, she explained. “They were like, ‘No way. This is not hip hop.'” Perhaps not — Ambrose was inspired by carnivals, thus the shiny fabric — but she convinced her clients. “I said, ‘There are no rules. You break rules; I break rules,'” she recalled. The video was a watershed moment; the year after Ambrose started filling her styles with shiny, plastic-covered nylon, Dolce & Gabbana sent models wearing that same material down the runway.

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