Infinite Jest, David Foster Wallace. First Edition.
David Foster Wallace (1962-2008) was an acclaimed American writer, and one of my favorites. The Lost Angeles Times called Wallace "one of the most influential and innovative writers of the last twenty years" and he's influenced an entire generation of writers. In fact, it's hard to find someone that reads lit who hasn't heard of Wallace. He won a host of awards, including the coveted MacArthur Genius Grant. His work his at turns hilarious, depressing, prophetic and dense AF.
Wallace's second novel, Infinite Jest, was published in 1996 and is widely considered to be his magnum opus. At over 1,000 pages and with hundreds of endnotes, it's an encyclopedic and challenging work. It's unconventional narrative structure is actually modeled after the Sierpinski Gasket. There's a lot going on plot-wise, but there are essentially four interwoven narratives – a group of wheelchair-bound Québécois radicals planning a violent geopolitical coup, a half-way house for recovering addicts in Boston, students at a high-level tennis academy, and the family history of the Incadenzas. These elements are all seemingly connected by a film made by the patriarch of the Incandenza family called Infinite Jest. The film is so entertaining that viewers will lose interest in anything other than viewing it until they eventually die. The novel made Time magazine's list of the 100 best English-language novels published between 1923 and 2005, and has been lauded as a high-mark of the modern literary landscape. This is the first edition, third printing, signed by Wallace on the title page: