2. Hunter S. Thompson

Most celebrated books: Hell’s Angels (1966), Fear And Loathing In Las Vegas (1971), The Rum Diary (1998)

Life story: It doesn’t take much effort to understand why Hunter S. Thompson is the first name that hits brains whenever the words “crazy” and “writer” are lumped together. After all, we’re talking about the guy singlehandedly responsible for the term “Gonzo journalism.”

A non-secretive expert in all kinds of drug use, the Kentucky transplant battled against more personal demons than an entire fraternity of exorcists; he was also an outspoken hater of politicians (namely Richard Nixon) whose love was reserved for guns, a predilection that fittingly brought him into the afterlife in February 2005 when he shot himself in the head, while locked up in seclusion, rather than grow old with his medical ailments. In his 67 years, though, Thompson lived harder than within some weeks than most people do for months on end.