Glee (S6)

Available Summary:

"A group of ambitious misfits try to escape the harsh realities of high school by joining a glee club headed by a passionate Spanish teacher." -IMDb.

Jack's Summary:

Dot-Marie Jones, an actress, portrays Sheldon Beiste, initially introduced as Shannon. You can watch one of his transition-related scenes here, where he is returning to work for the first time since transitioning. It's one of the most awkward things I've ever seen, but in all honesty, I think that's more indicative of Glee's writing than anything else.

You can read an article here about Jones's approach to playing a trans man; "I just pray that it comes across how it felt," she says, elaborating that she approached the role with "a lot of heart and soul and with the utmost respect." Much like 3 Generations, this can be considered an example of unideal casting which shouldn't be repeated, but that doesn't mean the actress herself had any cruel intentions. There is a Wikipedia page dedicated to Sheldon here, if you'd like more information.