Fun With Dick and Jane (2005)
I haven't seen the original 1977 version of this movie, but now I want to. I've heard that the original is better, and this one was pretty good. I laughed several times. I appreciated the downward financial spiral of the couple, where they didn't just live on credit and act like nothing had happened: it was hyperbolic but also strangely realistic. Of course your house isn't an asset if you don't actually own it, and it seems like people have forgotten that nowadays.
I think I've said before that I like movies in which married couples are on the same side instead of pitted against each other. Fun With Dick and Jane has that going for it, too. Dick and Jane like each other, and they make a good team.
I loved their son who spoke with a Mexican accent (because he spent all his time with their Mexican housekeeper/nanny), the nods (and "Thanks to" credits at the end) to all the recent corporate criminals, the almost-sex scene between overscheduled spouses. And if you want to see something really hilarious, watch the deleted scene on the DVD called "Let's Be Spontaneous" (I think), which continues that scene. I thought it was, well, hilarious.