Late Last Night (1999) from Johnny Web (Uncle Scoopy; Greg Wroblewski)

Late Last Night is an offbeat comedy scripted and directed by Steven Brill, who also wrote and directed Little Nicky, then tool the helm with another man's script for Mr. Deeds.

Don't be scared off by that resumé. Although it came earlier in his career, and had a non-theatrical release, Late Last Night probably comes closer to being a good movie than either of those high budget Adam Sandler vehicles that Brill directed. In fact, Late Last Night has some genuinely positive elements, although they just didn't quite manage to coalesce into a solid whole.

Emilio Estevez plays a man whose wife has left him. He genuinely loves her, and didn't see the split coming, so his reaction is a combination of hating her and hating himself. On the day she loads her U-Haul and moves out, Estevez heads out on an extended bender. He begins by drowning his sorrows in an alkie bar, but that turns out to be the wrong place to turn for empathy, since the jaded regulars and the bartender simply bait him in order to get him to bare his soul - all so they can make fun of him. He realizes that he has to have a sympathetic ear, but dozens of phone calls prove unproductive until he reaches a mysterious ex-friend played by Steven Weber.

Weber leads Estevez into a crazed walk on the wild side, buying crack from strangers, picking up coke whores, attending orgies, stealing cars, breaking into hotel suites, playing midnight golf by the headlights of a cadillac - a veritable frat boy's wet dream of an evening. Weber says and does everything that Estevez has only read about during his conservative marriage. This works on one level, at least temporarily, until we see that Weber's behavior crosses over into the surreal and we then realize that he is not a real person at all, but just some kind of doppelganger who has been summoned from the Estevez subconscious to do and say the things that are impossible for Estevez's timid conscious personality.

The time when we realize that Weber is an alter ego (Weber answers a question by breaking into a Broadway song and dance number, using the local coke whores as a back-up chorus. He's pretty damned good, by the way!) is about the time when the movie stops working, because after a certain point we just don't know how to assess Weber's behavior in relation to reality or even in relation to Estevez's thoughts. Are we to assume that  Estevez actually did say the words spoken by the Weber character? Or are we to think that Weber only represents what Estevez would like to have said, and that Estevez actually remains timid in these situations? Is Estevez even in these situations, or is the evening some kind of dream that happened after he passed out quietly in the alkie bar? Does Estevez himself know that Weber is imaginary? He seems not to - but he also seems so drunk and stoned that our interpretation of events is polluted by his own altered consciousness. In short, we simply can't tell what is happening and what is not, and this makes the author's thought process hard to follow. That's a shame, because the film has an underlying sweetness and humanity that might have delivered a strong emotional punch if managed better.

The end of the film involves some philosophical and sentimental reconciliation between the two halves of the Estevez personality, a change in tone which is marked by more than a hint of gentle poetry, the kind of regretful ruminations that might actually happen at the end of a frenetic evening, when the bulk of the drugs have worn off and quiet sadness has replaced the frenzy.

Anyway, the film is not so bad at all. If it doesn't quite work, it is not because it shot too low, but because it shot for the stars now and then, and didn't quite have enough thrust for lift-off. I think it could have been quite an enjoyable movie if it had not been so ambitious, and had been more straightforward - without the uncertain reality and occasional surrealism. I think I would have liked it much better if the film had used an omniscient POV instead of the Estevez POV, so that I could have understood what was actually happening in the real world, which could then in turn have allowed me to understand when and why Estevez resorted to alternate internal realities.