If you have any affection for The Simpsons, I can't recommend more highly John Ortved's oral history of the show, The Simpsons: An Uncensored Unauthorized History.
The book focuses on the creative process that led to the show's miraculous early run, and on the financial windfall that fell upon, and destroyed relationships among, the creators of the show.
Ortved does an effective job of weaving a compelling narrative drawn from previously-published and first-hand interviews. By and large, the narrative remains fixed on the now-legendary writing team (including someone named Conan O'Brien) that was the true heart of the show. You get a real sense of what it must have been like in the writers' room, where this collection of talent, protected from network interference by powerful producer James L. Brooks, was set free to create multi-leveled, satirical, anti-authoritarian, classic television.
I'll tell you what I learned from, or had confirmed by, Ortved's book:
1. Matt Groening's role on the series was quite different from what he, and Fox Television, would have you believe. The heart and soul of the show was, more accurately, its first showrunner, Sam Simon, and its most influential, long-time writer, George Meyer. Meyer's role, in particular, was made quite clear a number of years ago in a fascinating New Yorker profile, but it turns out that, if anything, the earlier magazine article may not have given Meyer his due.
2. Money ruins everything. OK, maybe not if you're the one getting the money. Then how about this - take a beautiful situation, throw a really big bag of money in the middle of the room, and watch everyone turn into animals.
3. The best creative work is made when creative people are left alone. It doesn't always lead to brilliance, but it's certainly more likely to occur. Everything that's best about The Simpsons - its unique voice, its literacy, its complete and utter disrespect for the institutions that we're told are the pillars of society - most times would have been diluted or killed in its sleep by network executives. It doesn't make execs evil; they're just after something - dependable, non-offensive, universally appealing - that's diametrically opposed to the elements that often lead to great art. Think about what's best in television - The Simpsons, The Wire, The Sopranos, Arrested Development, Mad Men, Curb Your Enthusiasm - all of it is unique, outside the box, fiercely idiosyncratic. It's a wonder stuff like this ever sees the light of day. (One of the parodoxes about The Simpsons is that a show this risky at its inception became a virtual money-printing machine.)
I also realized, as I blasted through this book, that one of the things I love most in anything creative is work that is so good that I cannot ever imagine being talented enough to produce it. I understand that some people embrace art that looks and sounds like something they could do - hip hop, punk, and other great art forms are built on the premise of erasing all lines between artist and audience. I get it. But there's just something about being astonished by the talent of others.
The best part of Ortved's book is that it dwells not on the resulting work (there are remarkably few recitations of the best moments on the show) but rather, on the astoundingly talented people who created the show.