Stepping in gum. Tricky crossword puzzles. Getting caught with your fly down. Even the coolest, most successful dude on the planet is subject to the daily indignities that plague the rest of us, and now, in the very funny hands of cartoonist Ali Graham, it’s a pleasure to giggle at his myriad mundane struggles. Ali started the99 Problems Tumblr in 2013, posting 99 illustrations in 99 days and gaining over 50,000 followers in the process. It received a groundswell of attention, including recognition as one of BuzzFeed’s favorite Tumblrs of the year, and Ali has since sold 99 Problems prints to fans around the world. The concept was inspired by a hit Jay Z song (one that’s “cemented itself into our cultural consciousness,” according to New York magazine), and each spread brings a new illustration and caption, from the trivial to the kind of issue more specific to a certain hip hop mogul and superstar. You don’t need to be a hip hop expert to get in on the fun, though casual and devoted fans of Jay Z will enjoy an extra layer of meaning to the book, appreciating references to song lyrics and supporting players in his life, like Beyoncé or Kanye West. It’s part of the cool factor, and they’ll love feeling in on the joke. Some illustrations will come from the original Tumblr, while others are brand new.