"CATCH YOU FUCKERS AT A BAD TIME?"

Posts Tagged ‘Rusty Schwimmer’

You Can’t Win (2026)

Wednesday, February 18th, 2026

ZERO EXTERNAL REVIEWS ON IMDB

I watched a curious new movie that nobody else seems to know about. Just came out on DVD yesterday, no fanfare whatsoever, and I couldn’t find any reviews or even promo photos of it. It says “based on the bestselling book by Jack Black,” but I don’t think it’s trying to trick us into thinking that’s the same Jack Black from I STILL KNOW WHAT YOU DID LAST SUMMER. This one spent his life riding the rails and stealing, and then he wrote a memoir about it that was published by Macmillan in 1926. I admit that I never heard of it before, but it seems it was a sensation in its time and it’s stayed enough of a cult book that it was reprinted by Amok Press. Apparently William S. Burroughs read it when he was a kid and cited it as an inspiration. (This was before Encyclopedia Brown.)

That seems like a book I should read, but more relevant for this moment it sounds like good source material for a potentially interesting movie. And what really sold me on it is that it’s directed by Robinson Devor, whose debut was the excellent Charles Willeford adaptation THE WOMAN CHASER. He also did the documentary ZOO that some of you might remember me reviewing for The Ain’t It Cool News.

YOU CAN’T WIN is kind of like an evil cousin to TRAIN DREAMS. It’s another hazy, non-linear contemplation of a quiet, simple man’s life in the late 1800s and early 1900s. Both were filmed and partially set in Washington state, and IMDb says they share nine crew members, plus Will Patton (THE POSTMAN), who appears on screen this time, he’s not the narrator. Both movies include problematic encounters with Chinese immigrants (this guy gets caught trying to steal from James Hong). But while Mr. Train Dreams spent his life working what was considered an honest job and yearning to be home with his family, this Jack Black does nothing but crimes for most of his life, always riding the rails, never sticking in one place except when he gets locked up. He does have a girlfriend at one point, he finds her on a river bank crying, she seems like an interesting character who says her name is Annie but implies that’s not her real name. I believe they stick together for a while, but whether that can be measured in weeks or years I couldn’t tell you, because those sorts of things are never made very clear in this movie. (read the rest of this shit…)