Always one...

Or in friends, those repeated transphobic episodes AND gay jokes

The biggest mistake here is watching Friends in the first place. What a shitty TV show.
- I've always hated friends. I hate it so much I can't even understand how someone can enjoy it. It's just as bad as The Big Bang Theory.

There's an episode of Space Ghost Coast to Coast where the guest makes a transphobic joke and Space Ghost just stares at them, which is his default behavior given the nature of the animation, but I choose to interpret it as disapproval.

Weirdly, one show that didn't make fun of the trans person in that one episode was The IT Crowd, even through the creator is a bigoted fucktard in real life.

You may be misremembering. That episode ended up with the trans woman being assaulted, and had a whole run of situational jokes about how she liked typically manly pursuits.
It got so many complaints the episode was pulled, which was the trigger that let him go mask off with his transphobia.
- It ended with the trans woman being assaulted
  I will say for that scene, at least she won and beat the ever loving piss out of him. Not exactly a silver lining but I did always appreciate the trans woman beating up the transphobe

I recently encountered it in 90210, IASIP, and countless movies (ace ventura 🤮)

No wonder trans people have it so shit. People grew up with this nonsense.

IASIP is honestly incredible for the trans rep it has though, especially for 20 years ago. It shows Carmen living a happy and fulfilling life as an absolutely gorgeous woman, contrasted against the Gang being miserable and shitty, it's basically some of the best rep in a sitcom IMO. As is the case with IASIP, the joke isn't at the expense of the minority, but at the Gang for being pieces of shit. They're not telling you to laugh with them when they're like "Omg woman with a penis!", you're laughing at them for how incredibly shitty they're being to this person. I find Lily Simpson's breakdown pretty great.
- Always Sunny goes out of their way to play really shitty human beings. And then flip the script so they're always seen as shitty human beings.
  Anyone who thinks the Gang is behavior you should emulate is really missing the point.
- This reminds me of the regular problem with these kind of comedies, that has been analyzed to death by essays on the internet. Shitty people have no self awareness or media literacy. So they don't notice when the show is making fun of them, and usually misinterpret the jokes as support for their shit POV. People who identify with George Constanta of Seinfeld, or bojack horseman, etc. They don't realize that the show is calling them out. They are not heroes, they're the butt of the joke.
- Ive heard that argument before and, ok sure i can see its validity - she's gorgeous! But as soon as they started misgendering her i was like nope im out.
The Sunny episode isn't really anti-trans though
- "Is that a hate crime? I think that's a hate crime"
There's reasons the second Ace Ventura movie is more well liked.

To be honest, most of the old sitcoms reproduce gender stereotypes super hard, some series are even based on it.

What if we kissed in the

unlikely situation where me - your old drinking buddy who you haven't seen in ages - transitioned and didn't tell you before we met up again?!

Love boat, is that you?

We hear you’re a transphobe now, father.

I need to rewatch Father Ted

the sex and the city biphobic episode just fucking wangs you across the brain with no warning.

I saw this recently but wasn't as surprised as I'd like to be. That entire show seems like a prime example of something that pretends to be transgressive while ultimately just upholding core social norms. I'm sure it was more legitimately forward thinking at the time of release, but looking back on it, I'm not sure it really was as much so as it's hyped up to be. It reminds me of how some churches have declared themselves more accepting of homosexuality. It's like, a concession made in exchange for keeping the core doctrines socially viable. In sex and the city, sex positivity feels like a concession, and the core doctrines seem to have a lot to do with gender roles, social hierarchy, consumerism, etc. I've only watched episodes here and there though so I may be off the mark.

I remember Two and a Half Men had an episode with an FTM character, and I vaguely recall it being... fine? I don't remember any of the jokes being mean-spirited, and the character was pretty much just treated like a man. Then again, it's been like 2 decades, probably, since I've seen it.

Becker had an episode that handled it pretty well I thought.

The very first line in the first episode of Vampire Diaries is a transphobic joke.

I don't remember a transphobic episode from Scrubs. There's no transphobic episodes in Scrubs, are there???

The main character drinks apple-tinis and is constantly called a girl's name. He's open about his love for his best friend, and refers to himself as a "sensey".
I've re-watched that show more times than I care to admit. There might be a few jokes that didn't age well, but I don't recall anything transphobic.
- Phew, thank you for confirming my memories. I would have been pretty bummed out should I have found out that even Scrubs had some problematic episodes as it is still one of my favourite shows
I last watched it about 10 years ago and I do remember there being a few jokes that are pretty cringe, mostly fat jokes IIRC. But overall it’s pretty good. There’s an openly bi/pan character and it’s never part of the jokes about him.
- No one can hate The Tod
- I also haven't watched it in 10 years but I still vividly remember most of the show. Still, my memory is starting to fail me and I wanted to be sure about it. Thank you for taking the time to reply <3