We weren't too far into COMPANY MAN when we paused it and started discussing whether or not to bail and move on to something else. We decided to give it just a few more minutes. Next thing you know, there's Woody Allen (!) on the screen and, before we had time to get over the surprise, we were laughing. Up until that point, the comedy had been labored and the jokes obvious. After Mr. Allen's appearance, the comedy remained labored, the jokes remained obvious, but for some reason I haven't been able to figure, much of it became very funny.
I can't speak for my co-habitant (who professed not to like it much at all, but laughed almost as much as I did); maybe my mood just lightened; maybe I just suddenly accepted that this was broad, anything-for-a-laugh burlesque; maybe it was the gin and tonic I mixed for myself while we were deciding if we should finish the silly thing. Who cares? It simply began scoring well on my "laugh out loud scale," and I relaxed and enjoyed.
I don't mean to mislead. COMPANY MAN is wildly uneven, and there is at least as much chaff as wheat. Think of it in the same way as you would an episode of the original "SNL:" what you're seeing at a given moment may be forced and tiresome, but wait a few, and something funny (however cheap it might be) is just around the corner.
If you see this movie, and decide that I or any of the other commenters here who thought it was funny (or should that be whom?) are out of our minds, believe me, I do understand.
Maybe you just have to be in the right mood.