The biggest, most glaring omission from my recent 100 Movies post was Albert Brooks' Lost in America (1985) -- a film that remains nearly perfect for me. Raising Arizona (1987) has diminished a bit over the years from too many viewings but Lost in America -- a film I try to watch once a year -- remains as biting and funny as it was when I first saw it on videotape back in late 1985 or early 1986, as memory serves.
It is easy to compare Brooks to Woody Allen and there are numerous similarities, obviously, but the big difference for me is that Woody Allen always wants to be liked; the "Woody Allen" character in each film is not that thinly veiled and always gets the best lines. Brooks' characters are not necessarily likable -- his Robert Cole in Modern Romance (1981) is quite annoying and, at times, almost pathological -- but they always seem true to life.
Lost in America is one of those rare films that succeeds as a comedy and as a deft, almost effortless satire of a certain type of American of the 1980's; it would be too easy to label this type "yuppie" or "baby boomer" as some of the traits continue to this day in many people (myself included, at times) -- white American consumer, for lack of a better term.
I think the film masterfully works as a portrait of this one couple and as a document of the era. The scene with Brooks trying to get his money back from casino owner Gary Marshall is still one of the funniest bits of comic business I've ever seen on film -- I don't laugh out loud like a moron every time I see it and that's what elevates it above the kind of nonsense that masquerades as comedy these days (the majority of the Judd Apatow stuff, for example). This is how to write a film comedy and Hollywood can't seem to handle characters with any nuance anymore.
This clip from Siskel and Ebert At the Movies provides more information on Brooks and his then-current third film, Lost in America: