Usher has a net worth estimated to be about 180 million. That's generational wealth. You can live an expensive lifestyle and not spend that amount.
If he's out there tryna get attention to stay relevant or whatever, it's not for the money. He has enough. It's the drug that consumes 99% of entertainers: fame.
They need it. Many if not most will do anything for it. Including them ritualistic stuff if the person can get them back on top or to stay on top and be nationally loved and famous.
I've heard Busta Rhymes (and other famous Blacks) saying he suffered from depression. Dude worth 20 mil. (Sidenote, should have been bigger) which if any of us had we'd be on a white sandy beach on a Caribbean island right now waiting out the winter, living our best lives. But when you are famous and rich, you want that every day, all day, till you are 6 feet deep. Not possible or reasonable logically but that's the drug they are chasing. Fame and being loved.
Finally, the whole dress, women's clothing thing (and yes, that includes kilts in context), is well known and if you as a black man doing knowing exactly how its openly looked at, you gotta be in the sunken place. 40 years ago, you can kinda, sorta get away with it as an actor or comedian, because people didn't think that at first, but these days, its the first thing we thinking about.
I've recently seen videos of Busta Rhymes and others who are famous talk about suffering from depression, etc.