He launched into the indie film scene with the beautiful, poetic George Washington and then made the well received Snow Angels...and then before long he made the back to back punch of Your Highness and The Sitter.
I think when he finds a balance of arthouse aesthetic and stoner / frat comedy the results can be delirious. Pineapple Express and Eastbound and Down are hilarious, subversive, and just plain weird in a disarming and kind of disturbing way at times. But then he turns around and makes Our Brand Is Crisis.
I don't know, I just find his career trajectory really strange and at times it almost seems like he's taking projects on as part of some kind of meta / subversive arthouse experiment of his own. It's hard to picture the brain behind Stronger looking at something like Your Highness and thinking it's worth making. He's kind of like PT Anderson if he'd followed up Punch Drunk Love with straightforward Adam Sandler comedies.
And now, of course, he's doing the Halloween films. I thought the first one in this new series that came out a couple years ago was a bit over hyped, and it appears the new one isn't getting as much love from critics. I don't mind the arthouse comedies when they're actually good, but I sort of wish he'd go back to making more quiet films like Joe (which I think was sort of unfairly overlooked and got overshadowed by Mud since they had similar stories).
He's just an odd guy to place, and I guess maybe that's deliberate and he's taking on different kinds of projects to keep himself from becoming stagnant, but sometimes it really does feel like he's pulling a prank on his fans or something. I do find him to be sort of similar in spirit to PT Anderson with the dark comedy and quirkiness (for example, There Will Be Blood has some bizarre comic flourishes at times - I remember people chuckling in the theater at the "brother from another mother" line) but perhaps it's fair to say that Green just seems to be a little more lost and in search of a singular voice compared to Anderson?
I do kind of hope they return to Eastbound and Down eventually, as I think Kenny Powers is one of the best comedic TV characters America has ever produced. That show was just magical and weird in a way that I wish his films always were.