This one sounds like a joke but it's actually pretty serious. I've been a Gucci fan since the beginning, and it hurt me to my heart to see him go through—well, a number of the items on this list. Drugs, non-music nonsense, and recidivism have all laid their claims to Gucci's career at various points. He's, metaphorically and literally, "tweeted through it," but perhaps the real moment that it became apparent he did not have Lil Wayne-level crossover success in his future was the infamous ice cream cone tattoo incident.

From the beginning, there was a sense that Gucci was repping, in his music, for a pathologized underclass. And since the days of Tupac, this kind of music hinges, for many listeners, on a sense that the artist is interested in preaching to more than the "converted." That he's working at being some kind of a spokesman for those who've been marginalized in society. Not to get too high-minded about what is ultimately just a bunch of gangster rap. But it seemed like Gucci was going about it in an organic way, building an audience and moving toward the mainstream. Reaching that point is a very precarious high wire act: you walk carefully across without abandoning where you came from or walling yourself off from mainstream acceptance. If Lil Flip lunged too quickly for the popular title, Gucci, ultimately, fell back in the other direction. The ice cream tattoo, followed by V-Nasty collaborative records, made it seem like maybe this guy was a bit crazier than folks had thought.

Suddenly, his momentum seemed to stall. While he remains an influential, one-of-a-kind hood star, pop star status feels out of reach. Something to keep in mind when trying to destroy your career, particularly if you want to avoid selling in Starbucks one day: alienating the mainstream with a tattoo which will keep you out of an office job for life is the way to go.