There is no question that blackface is a racist trope too regularly used on film, TV, and in magazines. While not nearly as rampant as it was in the 1930s, there have been hundreds of instances of blackface employed in the past twenty years. Everyone from Paris Hilton to Ben Stiller and Jimmy Fallon to Billy Crystal has donned a form of blackface in an attempt to be funny, controversial, or — in Hilton’s case — cute. (The things people will do for a laugh.)
The most recent use of blackface is by a repeat offender, Chris Lilley (pictured above), who is the star of the new HBO series, Jonah from Tonga. The series, which follows the story of a Tongan teenager, features Lilley in brownface make-up and a curly wig. In other series, the actor has portrayed S.mouse, an African American rap artist from California and Jen Okazaki, a Japanese mother of three.
Sadly he’s not the only entertainer that is a repeat offender. From the early days of blackface in the 1930s to now, several actors and models have turned to the controversial make-up choice to portray a person of another race.
Photo: The Dolly Sisters/Twentieth Century-Fox Film Corporation
A popular actress and pinup girl of the 1930s, Grable donned blackface in three different films, including Coney Island, The Dolly Sisters, and Happy Days.
It’s hard to believe that one of America’s most beloved singers did blackface but Crosby rose to fame in the ‘30s when it was “acceptable.” He performed as a African American in five films, including Holiday Inn.
As previously mentioned, Lilley has worn blackface (or brownface) in several of his hit series, including Angry Boys and Summer Heights High.
Photo: Angry Boys/HBO
An Oscar-nominated actor of the ‘30s and ‘40s, Webb portrayed an African American in vaudeville as well as The Little Show and Flying Colors.
America’s other favorite crooner of the ‘40s wore blackface twice. The first in a Major Bowes short for The Big Minstrel and again in the 1960 version of Ocean’s Eleven.
Photo: The Jamie Kennedy Experiment/The WB
On The Jamie Kennedy Experiment, the comedian routinely portrayed African Americans in a number of skits. He also employed blackface on his MTV comedic reality show, Blowin’ Up.
It’s hard to believe Dorothy from Kansas would wear blackface, but she did in the late-‘30s in such films as Babes in Arms and Babes on Broadway.
Photo: Babes on Broadway/MGM
With no relation to Sarah, Palin is an English actor most famous for being part of the Monty Python comedian group. It was with the group that Palin donned blackface and later in the 1988 film, A Fish Called Wanda.
The Seinfeld actor notorious got into trouble when he used the N word in one of his standup routines, but he also wore blackface in Whoops Apocalypse and later in an episode of the hit NBC sitcom.
Another famous actor of ‘30s and ‘40s, Rooney often shared the screen with Judy Garland and also portrayed an African American in several of the same films.
Photo: The Merv Griffin Show/NBC
An American satirist, Paulsen ran for President no fewer than six times without ever being in real contention. Maybe it was something to do with the times he wore blackface on The Merv Griffin Show and Night Patrol.
Similarly to Chris Lilley, Ullman embodied a number of characters on her series, Tracey Takes On… Some of the portrayals included Sheneesha Turner, a 34-year-old security guard, Chic, a male Middle Eastern cab driver, and Mrs. Noh Nang Ning, which came under fire from the Asian-American community.
Photo: Tracey Takes On…/HBO
In 2009, Banks had the contestants turn blackface (brownface, yellowface, and everything in between) into fashion chic during a competition on America’s Next Top Model. Later, Banks modeled whiteface in a pictorial tribute to supermodels that received a muted reaction.
While not a person, the publication — especially its overseas counterparts — has routinely asked models to pose in black and brown make-up for high-end fashion shoots meant to be “editorial” in nature but inherently racist considering the lack of diversity in Vogue’s pages.
Photo: Vogue Paris
Of course, these examples don’t even cover all the instances of when fans were shocked by their favorite stars wearing blackface. Check out the most shocking — and downright disappointing — moments in recent pop culture history.