Hell's Angels
There's a reason why Hunter S. Thompson became so famous. And that reason is this book. Well, there's also his bizarre personality, eye-crossing wardrobe choices, ravenous appetite for drugs and his propensity to write himself into almost every article he penned. But Hell's Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gangs is what started it all.
In 1965, Thompson was a mildly successful magazine journalist when his Nation article on the Hell's Angels, "Motorcycle Gangs: Losers and Outsiders" earned him a book deal. But instead of reporting on the gang, Thompson joined it. He spent an entire year with the Angels, riding, drinking and partying with them (he never went through the official initiation process, though, and was always viewed as an outsider). Hell's Angels was Thompson's first book, and arguably his best. It catches the author in mid-transition from journalist to writer; the book is non-fiction and the Angels are the center of the story, but there's more than enough boozy, gonzo Thompson in there to make it a hell of a ride. (Watch a video of Hunter S. Thompson on Late Night With Conan O'Brien.)