I think his career path took a turn after he decided to go sober. He was done with the comedy stuff after HIMYM and has more than enough money to do whatever he wants.
He's doing a sci-fi out next year, with Rooney Mara, too. He definitely seems to have moved on from broader comedy. I think if he does more comedy it would be in the vein of a Coen Bros movie. He's probably perfect for them, actually.
I'm much more likely to both watch and enjoy a film if he's only attached as a producer and not a director, oddly enough.
Adam McKay is probably my favorite in that crew or scene or whatever, Talladega Nights and The Other Guys are so well crafted
Out of the directors he works with a lot, McKay is definitely up there. I actually find myself really liking most of Nick Stoller's work too, Sarah Marshall is a classic, Get Him to the Greek and Neighbors are hilarious and I think Five Year Engagement is pretty underrated. He even managed to make a good comedy sequel. He also absolutely packs his movies with hilarious people too
I think Funny People was the last thing he was involved in that I liked, but so much good stuff has come out of the Freaks and Geeks group that he gave a chance, so I can't complain about the guy.
I think it's two halves of two decent movies, but somewhere around the middle there's a weird tonal shift and it becomes a completely different film. I think it's good, but without that messy shift I think it could've been great.
Funny People knocks on the door of greatness then just completely runs away from it. Comedic ding dong ditch.
He's produced some really great, classic movies and tv shows but the movies he's directed have been blah (except for 40 YOV).
Every Judd Apatow Movie, Ranked From Worst to Best Not surprisingly, I find myself disagreeing with a lot of the pecking order here
I watched that movie a bunch as a kid when it was on video in the mid-90s. Then it had a comeback freshman year of college when friends and I re-watched it and found it just as funny.
I think the funniest thing he's done is The 40-Year Old Virgin, though I'm sure the cast takes most of the credit for that. Romany Malco is so good.