Obscure film recommendations?

Not sure it's what you're looking for, but here are two lesser known and offbeat films I've frequently recommended in this forum. One is Red Garters, a musical comedy Western with a minimalistic, surreal set more ferquently seen on stage rather than in a movie. It's the kind of film where all the men doff their stetsons when anyone mentions the Code of the West and funerals of gunshot and lynching victims (apparently the only types of local fatalities) are followed by a celebretory barbecue (no, not cannibalism). Star is a popular singer from the 1950s, Rosemary Clooney (George's aunt).

The other is After the Fox, a 1966 Peter Sellers comedy in which he plays an ace Italian gangster who tries to smuggle stolen gold bullion into the country by pretending to make a movie starring aging movie idol Victor Mature, whose parody of himself is one of the great delights of the film. Neil Simon coauthored the script. Vittorio De Sica directed, and must have recreated every problem he's ever had with obtaining permission from local authorities to shoot and in getting local villagers to take direction as extras in the scenes. Sellers going through the motions of shooting a nonsensical film while trying to concentrate on his real goal of smuggling in a gold shipment is a delight to watch, but the real payoff is when the prosecutor shows the resulting film in the courtroom as evidence. A funny film.

That's quite vague but Wristcutters comes to mind

I liked Wristcutters.. I'd second that.