Agree with others that it's a somewhat claustrophobic and intensely psychological film rather than a zombie gore-fest, but also has a lot of interesting exploration of the "social contract" and culture these three young peoply try to / are forced to fabricate for themselves in their weird zombie apocalypse situation. Consider the making and breaking of house rules, the games, the ritual tat project, the recording for a posterity that won't be there, and consequences of doing or not doing things right, and then how it ends for each of them. On one screening not sure how well it all hangs together, but it's a genuinely ambitious film - I'd compare it with Eggers "The Lighthouse" (2019) though rate that higher for an element of humor that's missing in this.
I agree with the favorable reviews here, using an "8" on my first viewing to mean watch more than once, and decide if it's as good or better. But I quickly missed seeing the Leth film that anchors the five challenges, which is clipped but never shown in its entirety - as the finished alternatives are. Choices of location, set, acting, sequencing and other variations in the challenge responses turn on the quirky style and themes of Leth's original "The Perfect Human" as much as von Trier's "obstructions". I was able to find a decent free stream on UbuWeb (also on Youtube) same evening, and would watch that again before giving "The Five Obstructions" another shot. As is, it's an engaging, humorous and edgy insight into creative process.
The film can be faulted for at least appearing to give too much to the mother/sailor side of the conflict, an appealingly sexy but eventually unconvincing romantic fantasy. The boy Chief is the other distracting trap for the viewer - he's the embryo of a crypto-scientific nerd who has less in common with Nietzsche than with a certain type of sclerotic, egotistical academic you'll find slowly going berserk at a second rate college.
Importantly, the Chief doesn't quite "get it" about his underrated disciple Jonathan and the Sailor. Jonathan is, or should be, the focus of the film because he is a more interestingly conflicted, assertive, and intellectually cogent character than any of the others - he is the Mishima surrogate, who tries to reconcile and meld the Chief's perfectionism with the sailor's fictional attraction. That requires canceling out the unacceptably artless "return" of the sailor, which is the "fall from grace." Restoring aesthetic grace to the Sailor is the shocking concluding project. Keep your mind's eye on Jonathan - even while heeding the siren calls of competing sex and death.
The casting is very good. Miles has the dreamy look and self-deluding spunk of a romance novel heroine. Kristofferson always plays "himself" and in this film his noble antique head, wooden cowboy self-assurance, and gravel-voiced platitudes work perfectly to attract susceptible but discerning Jonathan in the first go around and disgust him in the second. The young actor Jonathan was a real find - able to play the submissive but also a live spark when called upon - his is the subtlest but most important role in the film.