I don't know if The Office clips really count as they were
intentionally cringey.
I've been on a Hitchcock binge lately and, in retrospect, a lot of his films have some pretty cringey moments, although knowing him that may have been intentional.
One in particular is the "I am Ambrose Chappell" taxidermist scuffle scene from The Man Who Knew Too Much. It's so awkward and silly, and when it cuts to the stuffed lion at the end as if he's saying "what the hell was that all about?" I almost fell over laughing.
I can't find an embeddable clip, but here's a link to the full scene from TCM:
https://www.tcm.com/video/205011/man...rose-chappell/