This was a funny trope decades ago. It works if it helps move the plot of the story and not just throw it in for a cheap laugh. Now on Family Guy, Peter Griffin just dresses up as a woman for a cheap laugh and a cutaway gag. He is suppose to be straight but acts gay. There was one I accept with the cross dressing. He had an operation to be a woman because he was mistaken for a woman after he went into a transexual bathroom. After that, he regretted it and went back into being a man. But he still dresses up as a woman. I don't find it this trope funny anymore and I don't see much of it. Anybody?

It can be funny, usually if there's something more to the joke than a just a straight guy in a dress. I think the "straight guy in a dress" joke got overused in film and television, though, so there has to be more to it. It's not 1983 anymore, and we all long ago saw Tootsie and Bosom Buddies.

Reminds me of another poster on this board a few years back. He rarely posted but when he did it was always about the same thing. He would always asks about episodes of shows where people cross dressed like he had some kind of obsession with it.

I never thought it was funny.

you mean like "ha-ha" funny, or like "Why doesn't uncle Bob ever show up for family reunions?" funny?

you mean like "ha-ha" funny, or like "Why doesn't uncle Bob ever show up for family reunions?" funny?

"Ha -Ha" funny

Sure, it was funny and a reliable laugh-getter when the old-time comedians did it. Almost always done as a disguise to elude pursuers. Lou Costello, Joe E. Brown, Stan Laurel, Curly Howard, and just about any physical comedian worth their salt donned female attire at one time or another. It was part and parcel of being a good comedian, that talent for mimicry. Some really were great at it, knowing just where the edge was, between displaying innocence and embarrassment.

Nowadays? With the modern values of comedy? It would likely have a perverted slant, rendering it unfunny and unpalatable. Just like how all the over-the-top drag queens are about as funny as warmed-over death. Even worse, if a good, traditional attempt were made by some current actor or comedian, it would probably release some twitter firestorm from thousands of 'offended' transvestites, demanding apologies and calling for cancellations. Part of the whole deeply ******** era we now live in, which has practically made comedy extinct as an art form.

I never thought it was funny.

Neither did I.

They tried it again with Work It in 2012 and it was terrible.

On Monty Python's Flying Circus, The Pythons played most of the female characters in drag with others played by women such as Carol Cleveland and Connie Booth.

"Ha -Ha" funny

Ahh,...okay, then "No"...not funny.

I recall that Milton Berle had an act featuring this subject, and never saw much worth to it. Flip Wilson had his "Geraldine" character, which was mildly funny for the way he portrayed it as a pseudo aggressive militant type woman, but it really wasn't the gender bender aspect that was humorous.

The movie "Some Like It Hot" really went overboard with the idea, to the point where if Marilyn Monroe had not been in the movie also, I doubt I would have watched to the conclusion. Though I will admit at the very end with Jack Lemmon getting stuck with Joe E. Brown as a "penalty" of sorts, was mildly humorous in a "reap what you sow" sort of way.

I think back in the day, there may have been an "oh, it's one of those" aspect of novelty that made some people laugh...but today with so many being out of the closet all around us, I think that novelty has worn off.

The Bowery Boys pulled off a pretty funny drag scene in their 1952 movie Hold That Line where they dress up as women as part of a college frat house initiation.

Each of the detectives on Barney Miller did it for mugging detail.

The movie Some Like it Hot was way before my time. I saw it on tv and it is overrated and not that funny. The last line is the best part and is worth a laugh but that's it. This is the funniest film of all time? I don't think so. If you want to see a good drag movie, watch Victor Victoria. It stars Julie Andrews. In it she plays a woman, pretending to be a man, pretending to be a woman. Okay, it may have a woman cross dressing but she was way more believeable as a man and it was way funnier. At the end Robert Preston helped from going to prison by dressing up as a woman but at least it was brief. The Looney Tunes did this too but they had phenominal writing. I can't say the same for Family Guy. I agree with Timeless. With so many people coming out, the novelty has worn off.

To put a footnote on my previous post... while I find some humorous merit in old-time comedians doing sequences in which they don drag (almost always to elude pursuers), instances in which the entire narrative theme involves cross-dressing is something I almost never find appealing or all that amusing. Hence, I've never really cared for "Some Like it Hot," "Charley's Aunt," "Bosom Buddies," "Victor, Victoria" and the like. But hey, if Lou Costello puts on washerwoman garb to sneak away from gangsters, or Gilligan is trying to mislead some villainous island natives, that is ready-made fodder for some good-natured yuks. A grand old comedic tradition.

Jack Tripper was a woman in an episode of Three’s Company it wasn’t bad.

Depends on the person, if we’re talking about Myrtle Urkel then HELL to the no :lol:

Jack Tripper was a woman in an episode of Three’s Company it wasn’t bad.
Yeah, it looked pretty decent, in fact, I’m kinda ashamed to say this, but it looked kinda hot :lol:

Depends, if we’re talking about Myrtle Urkel then HELL to the no :lol:

He did it to win a car. But I'll admit he was funny.

Depends on the person, if we’re talking about Myrtle Urkel then HELL to the no :lol:

You got that right.

Don Knotts did it in a couple episodes of Andy Griffith.

Don Knotts did it in a couple episodes of Andy Griffith.

In that "mountain wedding" episode where he did it to deceive Ernest T Bass......and Ernest remained attracted to him even after the deception was exposed, It made me think of the movie "Deliverance"