AMC's "Mad Men," the hottest property in pop culture right now, thrives on the resurrection of taboos great (casual sexism) and small (smoking anywhere and everywhere), but the cable drama really outdid itself in last night's episode. One of the main characters, Roger Sterling, performed a rendition of "Old Kentucky Home" in blackface for the benefit of his Kentucky Derby garden party guests.

It was a shocking moment, one that this show specializes in. Just when you start to groove on the cool, retro suits and three-martini lunches, they go ahead and ruin the fun by pointing out how much better things are now. This show is like "Happy Days" Goes to Rehab.

Just how far have we come? Click here to see the video and more recent examples of minstrelsy in pop culture.



The Obama/Joker Poster

When this depiction of the president as "The Dark Knight"'s Joker started popping all across the Web this summer, some people wondered if the intent was somehow racist. While the weird combination of the movie villain with the stark banner reading "Socialism" argues against it, the poster was definitely evocative of demeaning images from the past.

The man behind the campaign to spread the posters says that wasn't the intent, but the images certainly started some conversations.

The Transformers: Stereotypes in Disguise

With the release of "Transformers: Revenge of the Fallen" came controversy over two of the film's robotic characters. Skids and Mudflap are jive-talking twin Autobots who serve little purpose in the movie beyond comic relief.

The pair drew comparisons to another blockbuster film's comic-foil-of-questionable-sensitivity, "Star Wars Episode One"'s Jar-Jar Binks.

Is Wayne Brady Gonna Have to Choke a Stereotype?

Actor Wayne Brady's self-lampooning turn on "Chappelle's Show" has reached legendary status, and rightly so, but was spurred on by a wisecrack that questioned Brady's "blackness."

In an earlier episode, Paul Mooney explained why white people liked Brady so much by saying "Because Wayne Brady makes Bryant Gumbel look like Malcolm X." Brady's response was a hilarious turn that tweaked gangsta stereotypes, as well as his own image.




Ted Danson Roasting on an Open Fire

The former "Cheers" actor landed himself in boiling-hot water in 1993 when he appeared in blackface at a Friar's Club Roast of Whoopi Goldberg.

Whoopi defended Ted's act, which she helped him write, explaining that the Friar's Club roasts are not for the faint of heart. She also explained that the act was a response to persecution they had endured for being an interracial couple. Considering all the negative press Danson got, apparently nobody got the joke.

Eddie Murphy Flips the Script

In case there were any white people wondering how it felt to have themselves boiled down to a few stereotypical mannerisms, Eddie Murphy happily obliged by donning whiteface makeup for this famous "Saturday Night Live" sketch.