Weiner is king of the hill right now, but it also must be said that serious, crazy fuck-you money happens if your show gets sold into mass syndication. Larry David has made north of $800 million off of Seinfeld. David E. Kelley is worth somewhere in the range of $250 to $300 million, and Steven Bochco is close to $200 million. The late Aaron Spelling was worth about $300 million, as well.
Of course, the days of such lucrative syndication and residual deals are probably numbered. My prediction is that, as content distribution opens up, TV writers will find it easier to become a millionaire, but harder to become a quasi-billionaire. We're entering a world in which there will be fewer Larry Davids, but more Matthew Weiners. Either way, TV writing will continue to be very lucrative at the top of the field.
And the path to the top may get shorter. The days of paying dues for 10 years at the staff/producer level before having enough juice to sell an original series are relics of the network TV business as it currently exists and has existed; the democratization of distribution, and the hunger of new distributors for original content, will open up the field to younger writers. More and more young writers will get their start shooting spec pilots or series, too, and not just trying to get staffed on existing shows. It's not unheard of, this day and age, to make a name for oneself on the internet and then get drafted by Hollywood. Look at Andy Samberg and his Lonely Island cohort, for instance.
