There's a fair few Japanese crime films from the 1950s and 60s that have fun-sounding titles and end up being breezy, cool watches. I thought Cruel Story of Youth was going to be one of them, but I was off the mark. It's a darker and often confronting crime melodrama that I guess you could also describe as a twisted romance, but even that's a stretch, as the core relationship in the film is extremely troubling and is viewed by the movie as such, too.
That's to say the film's intentionally dark and unsettling, but that doesn't mean everyone would like it. That's also par for the course when it comes to director Nagisa Oshima. Naturally, this 1960 release isn't as extreme as his boundary pushing films from the 1970s onwards, but for its time, it would have been shocking. IMDb tells me it was banned in the UK, and only passed with a 15+ rating there in 2008.
Oshima is a great filmmaker though, and one that deserves mentioning alongside the likes of more well-known legendary Japanese directors like Akira Kurosawa and Masaki Kobayashi. This one is not one of his very best, but it's very solid overall, and holds up well, in that its core story about a troubled, rebellious, dangerous, and youthful romance still has moments that are unsettling and impactful.
So overall, definitely not a fun gangster/crime flick as I expected, but what was there instead was quite impressive in its own right.