It’s not only future right-wing conservative Supreme Court justices who engage in youthful hijinks involving blackface; once upon a time, the young Virginia Woolf and her friends did something much the same, impersonating the Prince of Abyssinia and his entourage and convincing the CO of HMS Dreadnaught to give them a royal welcome and an official tour.
(That’s Woolf on the far left, in drag and — frankly — fairly unconvincing makeup.)
Everybody seemed at the time to regard this as a jolly good prank, with the exception of the British Navy, which was embarrassed. (What the Abyssinians thought about the whole affair doesn’t seem to have been recorded — if, indeed, they heard about it at all.)
There’s a 2017 New Yorker article about the affair that waxes pontifical about the symbolic meanings underlying the hoaxers’ acts. It makes some interesting points . . . but as far as I can tell, the hoaxers were just upperclass intellectual twits whose agenda, if they had one, could be boiled down to “make Authority look silly.”