It's all subjective, right? I mean, the generation before me really has a hard time understanding the comedy of Jim Carey, Ben Stiller and Will Ferrell. It's just not as funny to them as it is to a large contingent of my generation (Generation X).
I live in a world of delusion, but what I think is that Hollywood had a supremely vintage year in 1999. Fight Club was the last honest movie ever made in America. Galaxy Quest is in my pantheon of favorite comedies. The Matrix. The Sixth Sense. Magnolia. The Talented Mister Ripley, The Green Mile, South Park: Bigger Longer and Uncut, Bowfinger, Office Space, Jesus' Son, Eyes Wide Shut, Sweet and Lowdown, Lock Stock and Two Smoking Barrels, The Red Violin, Dogma, Titus, American Pie, Muppets from Space, Mystery Men, Girl Interrupted, The Mummy, Angela's Ashes, Any Given Sunday, The Spy Who Shagged Me...
Spike Lee's The Summer Of Sam. F*@kin A!
These were the movies of 1999, a partial sample of them. Technically, The Big Lebowski came out in theaters during 1998, but it bombed at the box office and was not appreciated until it came out on video tape in 1999.
Since then, feature films are in decline, with a few exceptions, unless you are an addict for comic book movies.
On the rise is the quality of cable television, and on-demand programming. I think that's been obvious since top billing actors starting branching out into television (as opposed to Clooney going from ER to the highest echelons of Hollywood). Never during the history of the universe has it ever been a better time to be a writer for television.