It was highly critiqued at the time and it was irrelevant for most. I am big admirer of Matthew’s Weiner style so I gave it a try this pandemic.
Just as The Romanoff and Mad Men, you can say it is a slow burn with layers. And, just as the Romanoff and Mad Men, it touches the same themes: “the life not live”, “identity”, “hollowness of beauty”, “loss of identity by a crushing system” and the “ideal version of freedom that comes by living in the nature or outside of society” (too large for a theme, I know I can make it simpler but, what the hell?).
It is good? Is it bad? What do you think? I am very curious.

Here are my thoughts:

the movie starts with depicting the life of a man (Owen Wilson) who bought his importance with his image working as a weatherman. It is seen as beautiful on the outside and, of course, horrible and uncannily self-aware (just as Matthew like them) on the inside. He knows that there is a deep and there is a shallow, but he chooses the shallowness because it comes easier and natural for him (facing the obvious consequences of this life style).
Then we have the other extreme: his best friend (Zach Galifianakis). He chooses what he considers “true” and “substantial” (of course, he is clinically crazy but that just makes the idea ambiguous (which is great, by the way)). We can see that, thanks to this choice, he is seen as an outcast, a misfit and, maybe, a miserable person who really has not capacity of completing anything that he set his mind on (typically of psychosis). This poses the question: “is it because he is crazy or society doesn’t let him?”. Then, the movie, gave him tool, and therefore, the real capacity to make something out of his wishes: money. Will it bring him happiness? Will it bring him, finally, the possibility to start something and finish it? Of course, the realities of the responsibilities come crushing into him and he has to confront his own identity and realized that he is not fit to live without medication.
In the meanwhile, we have another “beauty on the outside”, the love interest which end up having sex with Owen Wilson and his best friend. This love interest proves, once again, that a beautiful husk is just the prelude to an ugly end (a theme that is constant in Matthew’s creations).
As I am describing this movie, I realized that Owen and Zach are two coins of a whole person. It is not coincidence that Owen’s best friend is played by Zach Galifianakis, a fat and ugly (by social standards) person. But if you combine both, we have a better human being.
So the movie offers the best and the worst of opposites worlds but ends in a heavy note:
Zach Galifianakis having a normal life, satisfy and with the prospect of love. In the final scene, he is outside a supermarket (I think). He sees a mechanical horse and he puts a coin in it so a child can ride it... then, he stares at the horse like someone staring at the abyss. He has this silent epiphany: he realize how mechanical his identity has become in exchange of coin, just like the horse. The movie ends there.
I like it very much but I am curious what people do think about this. It is clear that the movie has a message that begs the time to think about it but... is it really that bad or is it really that good?