Whites as blacks: Risky, rarely successful

A cultural memory of blackface: Burnt cork, red lips. Steppity-steppity-step, shuffle, slapstick. "Authentic" former slaves, dancing for the white folks. T.D. "Daddy" Rice, a white man in the cork and face paint, a national sensation in the 1830s, doing a dance he lifted from a black man in Cincinnati.

"Wheel about, and turn about, and do just so;

"Every time I wheel about, I jump Jim Crow."

(The song and dance seep so deeply into the cultural id that that phrase later becomes code for racial segregation.)

Blackface fades but never goes away, the greasy rub between the fingers of racial loathing. The insulting nature of it: No one turned out in blackface to play Scott Joplin's "Solace" or, as the 20th century slid by, Duke Ellington's "Solitude." No one used burnt cork to portray Romare Bearden painting "The Street." The joke is ignorance, the subject is black.

Time morphs. Swing, bop, civil rights, modern, postmodern, new century. Now things are complicated. Blackface has long been taboo, but now it's not all about insult. Now olive-toned whites play light-skinned blacks, without a sense of irony (Angelina Jolie darkened herself to play Mariane Pearl in

A Mighty Heart

). Since we're all supposedly postracial, some white comedians think it's allowable to use makeup to portray black characters with empathy or just for laughs.

Fred Armisen is Barack Obama on

Saturday Night Live

. Robert Downey Jr. plays a pompous white actor playing a black soldier in a Ben Stiller movie,

Tropic Thunder

, due out this summer. Chuck Knipp does drag as a black Southern woman, Shirley Q. Liquor, the "Queen of Ignunce," in clubs and on video-sharing sites. Comedian Tracey Ullman dons face paint to portray a black security agent, Chanel Monticello, in her new series on Showtime.

For better or worse, Ullman goes for it all. In the opening minutes of the March 30 debut of her show, "State of the Union," a mockumentary about a day in the life of America, she plays an undocumented Bangladeshi doughnut maker, a Jamaican caregiver (whose elderly charge tells her to get "your black hands off me") and a midmarket Hispanic TV news anchor. That's a white actress going brown, browner and light brown in about three minutes of airtime.

Downey, whose reps declined an interview request, talked to Entertainment Weekly recently about his role: "If it's done right, it could be the type of role you called Peter Sellers to do 35 years ago. If you don't do it right, we're going to hell."

Ullman was "unavailable," according to her reps.

"In America, there is this fascination that white folks have with black people and black culture, especially considering the special and sometimes psychotic relationship we've had over the last 400 years," says John Strausbaugh, author of

Black Like You: Blackface, Whiteface, Insult & Imitation in American Popular Culture

, a 2007 study of minstrelsy. "Taboos come and go, and maybe this taboo is lessening lately."

Though the burnt cork and garish lipstick seem consigned to the bin of bad taste, there are different levels of subtlety in whites playing black dress-up. Maybe it's becoming possible in an era when interracial friendships and romance exist much more freely for whites to do impersonations of black characters well and affectionately, and vice versa. Billy Crystal's take on Sammy Davis Jr. on

Saturday Night Live

several years ago was spot on, but Crystal was gifted enough to make it more about celebrity and friendship than about race. It had the critical assets of being (a) funny and (b) not at all caustic. The Wayans brothers and Dave Chappelle have reached for the pale greasepaint to play whites as well, to varying degrees of success.

Armisen's take on Obama has drawn criticism, not so much for his characterization, which is understated and somber, but for

Saturday Night Live

having a lack of diversity on the show.

Screenwriter and author Trey Ellis (

The Tuskegee Airmen

) thinks that whites can, in limited circumstances, carve out some territory here. He notes that Jolie, who claims some mixed ancestry, "did a fine job" as the multiracial Pearl: "There are people on the margins of race that a lot of people could play them. It wasn't like Anthony Quinn playing Zorba the Greek."

Ellis also points out that, at least according to an outline of

Tropic Thunder

, Downey is not portraying a black character as a serious enterprise. The movie-within-a-movie premise is that a cast of self-important actors is filming a movie about a war. They are so overbearing that their director drops them into the jungle setting of a

real

war. Downey's character is to fill in for a black actor who dropped out of the cast - but he's so Methodized that he decides to play the role as a black man anyway.

"It's not going to be upsetting," Ellis says. "I think it's going to be done in such a goofy way for everyone to laugh at."

Goofy can work, although it's tricky. The rule is that the joke has to be on the white character, not the black one.

In the 1976 movie

Silver Streak

, costars Gene Wilder and Richard Pryor pulled off a scene in which Wilder's character puts on black shoe polish and garish clothes to disguise himself as a black man long enough to get past security guards on a train. Wilder coaches himself into acting "black," but he's so nervous, and so racially clueless, that the joke is on his character. Pryor's dumbfounded reaction to the jive-walking Wilder sums up the audience's take, and the bit works by the rules of the odd-couple buddy movie.

As whites become more familiar with black culture - any number of white authors, singers and musicians now perform in black styles - it can lead some actors into the minefield of overfamiliarity.

The new spin: White actors play characters so hip they can say whatever black people do, and it's OK because nobody would

ever

think they're racist, get it? This is apparently what Knipp is trying to get at in his portrayals of Shirley Q. Liquor. His character has 19 "chirrun" and is on welfare and talks about "labesians" and "homosexicals." It's like Daddy Rice and Jim Crow brought back from the grave. Rolling Stone called Knipp "America's most appalling comedian" last year.

Jabari Asim, author of

The N Word: Who Can Say It, Who Shouldn't, and Why

, says comedians like Knipp prove society is just not that far along.

"We all wonder what it would be like to walk in someone else's skin," says Asim (a former Washington Post editor now at Crisis magazine). "But to put it out there in public, or in a feature film, is a combination of [boldness] and stupidity."

This is another interesting thought, and one that the record bears out: Most of these impersonations blow up - and yet people can't resist trying them.

Burnt cork, red lips. Steppity-steppity-step. Images that never quite go away.