The video is an assault on the senses (but in a good way), as famed video director Mark Romanek takes his first shot at helming a rap video. Jay, who originally wanted Quentin Tarantino to direct until Rubin advised him to give Romanek a try, wanted to make a hip-hop video that 1) showed the Brooklyn where he grew up and 2) looked like photographic art. Romanek, who’s always had a flair for creating videos that doled out artistic expression, whether it’s Nine Inch Nails’ grimy, disturbing freak show "Closer," Beck’s Truffaut-saluting "Devil’s Haircut," Johnny Cash’s sad-eyed tribute "Hurt" or Fiona Apple’s voyeuristic "Criminal," immediately thought of cribbing from the black-and-white noir photography of New York photojournalists like Weegee. But the visual, urban bluntness also brings to mind the work of late, black photographer (and Brooklyn resident) Roy DeCarava, who captured black-and-white shots of Harlem in the early 20th century.

Much like DeCarava’s photographs, Romanek gets shots of African-American life, one after the other, in "99 Problems," with Jay serving as a tour guide of sorts. First shown outside the famed Marcy Houses where he grew up, eventually making himself at home in one of the apartments as he raps about music-industry gripes, action goes on all around him as the video progresses and Jay walks around his city, telling his tales.

Romanek takes off in several different directions throughout the video, zooming right into people’s face one minute, slowing down the whole momentum of one scene the next. But thanks to exemplary editing from longtime Romanek editor Robert Duffy, the video maintains a rhythmic pulse. It’s literally never out of step. But, just as Jay raps about the problems he’s had in his life—music-industry drama, almost getting caught by police with drugs in his trunk, having to go toe-to-toe with an idiot—"Problems" visually breaks down the problems that have plagued Brooklyn and inner-city America in general. As much as Romanek shows celebrations randomly popping off (whaddup, dude in Viking hat!), he counters it with bleak shots of black men in jail (completely naked, at one point, as they’re showered down) and old men prematurely mourning their loved ones in funeral homes.

As the video shows everything from a guy aiming a gun out an apartment window, pointing it to unsuspecting passersby, to street performers and step teams literally dancing in the street, it’s obvious that Jay and Romanek are both out to show Brooklyn as a land of contradictions. Good things can happen, but really, really bad things can happen, too. (In a New York Times piece on the video, Jeffrey Rotter said, "’99 Problems’ is a celebration and a disparagement of Brooklyn iconography.") And, yet, as Romanek captures it all with cinematographer Joaquin Baca-Asay, who would later work with James Gray on We Own the Night and Two Lovers, there’s a striking, visual poetry to it.