The movie gets credit for not making the high life seem colorful or funny. It is not. It is boring, because when the drugs are there they simply clear the pain and allow the mind to focus on getting more drugs.
The problem with most movies about junkies is that they're really not about anything but getting high, crashing and screwing up. The problem with most movies about writers is that they can't demonstrate a writer's talent. Put the two together and you've got Permanent Midnight. [18 Sep 1998, p.H6]
The framing device, which has Stiller recounting his tale to a fellow recovering addict (Maria Bello) over the course of a weekend sex session, stops Permanent Midnight dead in its tracks every time it pops up, but Stiller alone is almost enough reason to check out the film.
Perhaps if Jerry were a three-dimensional character, or the movie had focused on one plot instead of trying to do it all, Permanent Midnight might have been engaging. But in the end, all you see is another rich spoiled brat shoving tar up his arm, and at this point it's just too hard to care.