On one of his most successful singles of all time, Jay Z rapped about having “99 Problems.” When the song came up on shuffle one day, at least one of illustrator Ali Graham’s problems was solved—the problem of what his next project would be.
“All I could think about suddenly was, ‘What could those 99 problems be for a superstar rapper?’” Graham says. “I really liked the idea of Jay Z as a character having to deal with everyday problems—and some not so everyday ones too.”
From this thought train was born a tumblr collecting illustrations of Jay-Z’s 99 problems, ranging from poor table service to the inexplicable claim in one of his lyrics that “radio don’t play my hits.” After the 99 Problems tumblr caught on, Graham was left with a new problem, a more enviable one: how to expand his quirky digital project to meet the demands of a book deal offer now on the table. It turned out not to be much of a problem at all.
Prior to creating material for the just-released book, 99 Problems, the U.K.-based freelance creative had made other illustration and animation projects involving famous musicians, such as Beyoncé vs. Zombie. The 99 Problems tumblr seemed to resonate with people on a larger scale, though, so in creating the book, Graham strove to retain its universal appeal.
“I wanted a lot of the problems to have a few layers to them,” he says, “ so that hardcore fans will notice subtle references, but people stumbling across the project at a glance will just enjoy a cute, fun image too.”
The book takes some of the best images from the tumblr and adds new ones to the mix to keep them fresh. Some of the images that worked on the site proved too topical for the book. One featuring Jay Z and Pharrell wearing the enormous Arby’s-style hats that Pharrell popularized in 2014, for instance, was removed for being very much a product of the year 2014. Although the song that this whole movement stems from, “99 Problems” came out 12 years ago, it’s continued popularity in the Jay Z catalogue has rendered it timeless—a feeling Graham hoped to preserve with the book.
While the actual Jay Z is not shy about discussing his problems of not making enough money through streaming services like Spotify, readers of the book can disappear into its pages and imagine the superstar having to deal with other, more imaginative issues.
Have a look through some of them in the slides above.