There's few people who have managed to escape the phenomenon known as the "drag queen". For those unfamiliar with the expression, it borrows from the palare for "clothing" and by extension "to dress up" to describe a usually flamboyant or outrageous exercise in showmanship and cross-dressing.
Let's be exceedingly clear on one thing. Transgender is the idea that someone is gendered differently from their biologically-assigned sexual characteristics. Transvestism is the concept of sexual arousal or pleasure from wearing the clothing of the opposite gender. Drag is an act. Men (and women) who drag may or may not be trans- anything in their day to day lives (most aren't) but the concept of being a performer in same says literally nothing about their gender or sexual identity, though there are many who are gay or trans.
Men dressing as women for showmanship purposes has a long history. Before women were allowed on stage female roles were played by boys. It's part and parcel of the pantomime genre to have an older man dress outrageously to play the fairy godmother/kindly aunt character in a fairy tale (unconvincingly I might add) for comic effect.
But nothing prepares you for the sight of someone practically exploding through a curtain to "I'm every woman" wearing a six-inch thick makeup job that took an hour and a half to apply, wearing a wig that defies gravity. Speaking briefly and momentarily on the male -> female side the general idea is to come out brash, confident, and extreme. The body has curves, the outfit is sequinned or encased in marabou, the wig is 80s-level closer to God. We're not talking about pretending to be Hillary Clinton with a touch of eyeliner that accentuates the natural features in a subtle fashion, we're talking Alice Cooper levels of kohl to embody Beyonce or Liza Minelli, during their Vegas years.
Typically a performer has a character he or she embodies. Some go for a bona fide celebrity impersonation while others create a character of their own. Said character sings in his or own voice if he/she can, but many choose to lip sync over a prerecorded track. The persona is usually "fierce", aggressively sexual in some way, confident, larger than life, and in spoken word moments apt to be catty, lecherous, critical, with a steady repertoire of raunchy comments and perfect put-downs. But it's all in fun. As Atlanta's legendary drag den mother Charlie Brown commented during a planned mid-dinner roast of gathered birthday celebrants (to a woman who admitted she was from Alabama) "the only good thing to come out of Alabama is the I-20, honey, now blow out that candle and show us all how you paid off that trailer."
Tipping is encouraged, and many a performer walks away with handfuls of dollar bills enthusiastically handed over by screaming fans. That being said, the clothes and wigs are typically handmade and finding heels in a men's size 14 isn't exactly cheap either. It can be big business. Some of the most famous performers, like RuPaul, have club hits and television series. I didn't actually believe in the feasibility of La Cage Au Folles (the Birdcage in the US remake) until attending a dinner theater/drag restaurant as a guest of the wife's workmates - but there is a chain of drag dinner theater places and many a gay bar has a drag night and they're viable, and obviously highly profitable. The impresario at the place we went to looked like a shorter, portlier Robert Downey Jr. but it was at that moment I realized that it wasn't something either movie made up.
There are also drag kings but we haven't seen them have the same level of celebrity or impact as the drag queen. The challenges there are more obvious. It's easy to hide a five o'clock shadow under a layer of foundation, a man's square body can be filled out with a dress that looks like it came off the set of Zoolander, but it's a lot trickier to take a slender woman and make her look overly butch. The usual "go-to" effect is an effort-laden pomaded pompadour, suggestion of Homer Simpson type shadow, and an Elvis/Bruno Mars suaveness. If drag queens go for sensational fierceness, drag kings go for a swaggering confident Cary Grant style suave.
I'm not even going to go into the psychology of what this sort of thing says about how one gender views the other or idealizes the other, but I'll let better minds than mine sort that out. All I know is, I had a riotous good time with friends at one of these, and I'm decidedly a fan.