Basically, anyone donning clothing because such clothing is associated with that of the other gender is crossdressing. Doing the action doesn’t necessarily make one a crossdresser. And though the terms are interchangeable, some are highly offended at being referred to as transvestite rather than crossdresser and vice versa.
Perhaps because when the word transvestite first appeared, deriving sexual pleasure from crossdressing was part of its definition whereas the fetishistic element is no longer associated with its definition.
Simply put, the transvestite or crossdresser label— it’s personal.
As requested, I attempt to name transvestite actors or musicians.
Boy George could do some fierce makeup and crossdressed here and there. In the States, I remember my favorite childhood band, Nirvana, and Kurt Cobain sure did rock some dresses (very endearing, btw). Eddie Izzard is probably the most famous (Executive haha) transvestite in the West but I’m hard-pressed to find other examples of dedicated cross dressers. Sure, many actors and/or musicians crossdress but it’s rare that it continues after the role or performance.
Interestingly, in Japan, crossdressers have always been a part of popular culture, especially on TV. There’s an expression, talento, that serves as a catch-all for B and C-list celebrities, be they comedians, musicians, actors etc. who are also on any number of Japanese variety shows (think a cross between Celebrity Jeopardy! and The View) most nights. And you can always count on the token popular transvestite personality du jour (Matsuko Deluxe) as a regular on said show. Aside from the made-up-for-TV-ultra-glam transvestite, many guys crossdress in Japan. Skirts on men aren’t an anomaly on Tokyo streets, makeup for men is a thing that’s not just for a fringe group and here’s an interesting article regarding one aspect of crossdressing from RocketNews24. The old man with pigtail-beard-braids in the schoolgirl uniform is a noted figure in Tokyo who makes quite the rounds at trans parties (and he’s so damn cute).
Although public crossdressing in the States is relegated to drag queen culture, in Japan it is a much more seamlessly integrated part of popular culture. There are degrees to which one can crossdress without anyone giving two shits whereas in the States there seems to be a stringent need to categorize, compartmentalize, classify.
In the States:
Wait, you cross dress but you’re not a drag queen? Or gay? Hold up, you’re a transvestite and straight? (Research indicates that this is actually the case for the vast majority of transvestites).
No. No. Yes.
What. The. Fuck.
Whereas in Japan:
Your hair is so long! Are you using a special shampoo? And where did you get that skirt?!
Nah, I just brush it a lot and I got this at Parco (big department store), ladies department.