I was beginning to think that I was going to be the one to name this, and it sprang immediately to mind when I read the thread title.
I was shocked when I got so far into without seeing it. It’s an entire comedy movie based around awkward characters!
Maybe this isn’t what you meant by “cringy” but in the deservedly short-lived sitcom Mulaney (it never should have seen the light of day), Elliot Gould played the neighbor Oscar with every gay stereotype in the book, well, every effeminate one anyway. He didn’t cringe at all, but I sure did, followed by throwing up in my mouth a little.
The Big Bang Theory. Everything, from the smart but homely girl, the cute clueless girl, the guys. If it didn’t have a laugh track you wouldn’t know it was supposed to be funny.
Oh, and the laugh track itself is cringy. Ha, Ha, Ha,. Insert joke about Jeopardy here.
Must agree. The only I find not cringy is the calibre of guest stars, like Wil Wheaton and Stephen Hawking. The totally stereotypical depiction of nerdy people and their girlfriends makes me shake my head. Oddly, I find Young Sheldon much more tolerable. Maybe because they got rid of the laugh track.
Every character on Two Broke Girls.
Haaave you met Ted (Mosby from How I Met Your Mother)? Much like Ross from Friends, Ted is frequently mopey, passive aggressive, fickle, charmless, womanizing, and stalkery, often getting into cringey situations of his own making.