Jay-Z, photographed in the legendary Beat Street Records during the shooting of his “99 Problems” music video, by director Mark Romanek in March 2004. Hov had a long history with the store, with it being one of the first places to carry his early singles.
Hov wanted the “99 Problems” video to be as auto-biographical as the rest of The Black Album, helping to paint the portrait of where and how he grew up. In a conversation with Romanek he told him he wanted the video to “make a pissy wall look like art.” The task was originally intended to be undertaken by Quentin Tarantino, however during the planning stages Rick Rubin suggested that Hov offer the job to Romanek.
Due to the research and influence of Romanek and cinematographer Joaquin Baca Asay the video borrows visual characteristics from many New York street photographers, including Martin Dixon and Eugene Richards. The video was shot entirely on black-and-white film. Utilizing broken clips of footage captured in Brooklyn’s Marcy housing project, Hov and Romanek created an effective portrait of urban life. Somewhere between the almost photographic imagery and the rapid montage of cinematic movement, Romanek manages to convey Jay’s development and monumentalize his Marcy roots as well as the nature of the projects themselves.
The video’s final scene, which depicts Jay being sprayed with bullets, was inspired by the ending of the classic 1967 film Bonnie and Clyde. “I’ve always wanted to do a ‘Bonnie and Clyde’-type of scene for a music video, but no one had the guts to let me do it until Jay-Z came along,” Romanek revealed to MTV News. “Jay was a little unsure about it at first, because that sort of imagery has a lot of real-life baggage attached to it in the rap world, but I explained to Jay that it was meant to be more abstract, that it wasn’t meant to be taken literally. He finally decided to trust me and I think he really liked the way it came out.” Hov added: “As far as me getting shot, I just looked at it the same way I would watch Denzel [Washington] in 'Training Day,’ or seeing any other actor, you know? I was just acting out a part. I was trying to show Hollywood I got some chops, too. Maybe I’ll get a little job.”
MTV refused to air the clip before 6 p.m. and asked ask Romanek to edit about ten scenes in the video, but Jay agreed to only blur certain images: "We’re not interested in what MTV likes or doesn’t like. If you make something good enough, MTV will want to show it.” Hov has jokingly said he felt like Madonna at the time, relating to the controversies that surrounded many of her music videos.
In a later interview Romanek would sing the praises of the rapper: “Jay is a gentleman—cool, hardworking, and really funny. This was a longer shoot than he was used to and he sometimes complained (in a totally light-hearted way) that I was forcing him walk all over Brooklyn. But, I think he knew we were making something a little special and that since it was his last video, he was willing to put in the extra work. I think he has similar perfectionist tendencies so, he understood my process and the focus I put on trying to get that extra effort out of him and everyone on the crew.”