Infinite Jest

Infinite Jest is a long novel that takes place in a time somewhat similar to our own. Years no longer are known by numbers, but instead by their sponsors. Most of the book takes place in the Year of the Depend Undergarment. Things are somewhat different. It is part alternate history and part futuristic work (that is now in the past.) 

A good chunk of the book takes place at a youth tennis academy in Arizona. The people there play war games on tennis courts, takes various mind alternating substances and explore many aspects of their life.

A significant section of the book also takes place in Boston. We also hear a long discussion about Alcoholics Anonymous in Boston.

Parts of the book feel based on his experiences. Some parts are quite good. Other parts are offensive. The book is in the "future" but very rooted in the 1990s when it was written. Some parts of culture were carried to their absurdist limits (corporate naming rights for everything), while other parts seem to still be stuck in the 90s. It feels like something that would be fun writing, just not so fun reading.