Some things we failed to mention. The montage sequence from Bamboozled not only gathers blackface tropes from US pop culture. Note also the amazing score by Terence Blanchard laid over that clip. I would argue that the music functions as a melancholy yet dignified solvent, cutting through the visual sludge of minstrelsy with the sound of one of Black America’s most signal cultural achievements: Jazz.
The invocation of the minstrel figure continues to exert fascination and provoke explosive responses, from Wesley Brown’s novel Darktown Strutters (the title of a film and a song as well) to Little Brother’s 2005 album The Minstrel Show to American Apparel’s ill-advised ad “Sweeter Than Candy, Better Than Cake” (see below).
There are also abundant scholarly studies of blackface performance. Off the top of my head: WT Lhamon’s Raising Cain, Louis Chude-Sokei’s The Last Darky, Robert Toll’s Blacking Up, and Donald Bogle’s Toms, Coons, Mulattos, Mammies and Bucks, all of which I recommend.