Looking for movies with actors in black face? Blackface is the name attached to the form of entertainment where the performer is painted to appear as if they were African American. The practice started roughly around 1825 and1830. This is the advent of the “minstrel show.” The performer would usually paint their skin with burnt cork or greasepaint, make the eye and lip area more pronounced, and wear course wigs in addition to white gloves. The perfumer would act out the era’s prevailing stereotypes of blacks. In addition to whites, some blacks would also perform in blackface. While it was the main form of popular entertainment in America, the practice all but disappeared in America after the Civil Rights movement

When it comes to blackface in American cinema, the name Al Jolson comes to mind.

Al Jolson was one of the most famous celebrities in the early to mid-20th century. Jolson had a penchant of performing in blackface. One of his most famous movies in which he performed in blackface was the “Jazz Singer." Released in 1927, it was the first major motion picture film to have spoken dialogue. The plot revolves around Jackie Rabinowitz, who struggles betweens his Jewish culture and his profession as a jazz singer.

“Bamboozled” is a film released in 2000 and was directed by Spike Lee.

The film stars Damon Wayans as Pierre Delacroix, a producer for a TV network. His boss, Dunwitty (Michael Rapaport), rejects his black show ideas because they’re too tame. Unhappy, he comes up with a plan to get fired with help from Sloan (Jada Pinkett Smith), his assistant. He pitches a blackface extravaganza called the “Mantan: The New Millennium Minstrel Show.” He gets two black street performers (Tommy Davidson, Savion Glover) to star in the show and he renames them Sleep N’ Eat and Mantan. They perform on the show in blackface and to Pierre’s surprise, the show is a monster hit. But unbeknownst to him, this will have dire consequences in the end.

“Tropic Thunder” is an action comedy film released in 2008 and directed by Ben Stiller, who also wrote, produced and stared in the film.

It also stars Jack Black and Robert Downey, Jr. The film revolves around Tugg Speedman (Stiller), an over the hill action star that needs a new vehicle film to revive his career. He decides to turn a Vietnam veteran’s memoir, “Tropic Thunder,” into a film. He recruits comedian Jeff Portnoy (Black), Alpa Chino (Brandon Jackson), a rapper and Kirk Lazarus (Downey Jr.), a serious dramatic actor. For the role of Lincoln Osiris, a black man, Lazarus pigments his skin dark, wears a wooly wig and speaks in ebonics. Lazarus is a source of comedic tension in the film. The crew gets lost in the jungle and becomes embroiled in a battle with a drug smuggling ring. 

"Trading Places" is a film released in 1983, starring Dan Aykroyd, Eddie Murphy and Jamie Lee Curtis.

The film was directed by John Landis. It also stars Ralph Bellamy and Don Ameche as the film's main antagonists. "Trading Places" tells the story of Louis Winthorpe (Aykroyd), a successful managing director in the Duke and Duke Commodities brokerage firm. The owners of the firm, the Duk brothers (Bellamy, Ameche), decide to wage a one dollar sociological bet that if the roles of a rich man and poor man are reversed, then they would act as such. Thus, Winthorpe is driven to poverty and Bill Ray Valentine (Murphy) is made wealthy. Eventually, they both catch on to the plan and devise a way to take revenge against the Dukes. During the course of the revenge, Aykroyd dons blackface playing a Rastafarian.

"Here Comes the Navy" is a comedy film released in 1934.

It was directed by Lloyd Bacon and starred James Cagney as Chesty O'Conner, Pat O'Brien as Biff Martin and Gloria Stuart. Basically, Chesty gets into conflict with Martin, chief petty officer of the USS Arizona. To get revenge, Chesty joins the Navy and plots his course. On the way, he falls in love with the sister of his nemesis. Chesty puts on blackface for excursions off the ship with other black seamen.