1850–1870: Minstrel shows, early vaudeville performances in which white actors painted their faces black and caricatured the singing and behavior of slaves, are at their most popular.
1915: “The Birth of a Nation,” D.W. Griffith’s film based on the novel “The Clansman,” premieres. Famously one of the most racist movies of all time, “Nation” depicted the Ku Klux Klan during Reconstruction as valiant, noble heroes protecting white people from the vicious attacks of dangerous African Americans (who are played by white actors in blackface).
1920s–’30s: Major Hollywood pictures — including “Swing Time,” “The Jazz Singer,” and “Everybody Sing” — continue to include white actors in blackface.
1956: Yul Brynner, the actor who played the Asian lead in “The King and I” on Broadway, reprises his role in the film.
Aug. 30, 2009: In the third season of “Mad Men,” Roger Sterling performs “My Old Kentucky Home” while wearing blackface.
Nov. 7, 2012: Supermodel Karlie Kloss wears a Native American-inspired headdress during the Victoria’s Secret Fashion Show. Backlash was swift; the outfit was pulled from all the retailer’s promotional materials and the televised broadcast.
April 14, 2013: Selena Gomez wears a bindi and evokes Indian imagery to perform “Come & Get It” at the MTV Movie Awards. Hindu leaders from the Universal Society of Hinduism deemed her performance “insensitive” and insisted Gomez apologize. Gomez continued to wear the bindi.
Aug. 25, 2013: At the MTV Video Music Awards, Miley Cyrus performs. Cyrus’s dance, attire, and use of black back-up dancers leads to a wide-ranging, weeks-long debate about racial appropriation in modern pop.
Halloween 2013: Julianne Hough wears blackface to dress up as CrazyEyes from “Orange is the New Black” for Halloween. Public outrage was immediate; Hough apologized on Twitter, saying “I realize my costume hurt and offended people and I truly apologize.”
Nov. 24, 2013: Katy Perry dresses up like a geisha surrounded by dancers in Kabuki makeup to perform her song “Unconditionally” at the 2013 American Music Awards. She is accused of invoking a mash-up of Asian imagery and wearing yellowface.
— Jessica Goldstein