I never saw the point of laughing at the oppressed

E. D. Kain asked this question (which he really didn't answer) so I had to respond

You don’t quite answer the question you ask though I think you hit some points.

1) Modern conservatism only complains, it is angry ideology that does not assert anything positive. Angry comedians or singers or any type of artists only goes so far. And how far the “angry” art goes depends on the level of artistry. Like the art of the 3rd International it is most concerned with articulating a didactic message as opposed to attaining a level of lyricism through the commitment aesthetic excellence. There has been angry leftist art (ex. Pablo Piucasso’s epic painting Guernica) but what was that work angry about (slaughter, death, and the abuses of power)? What are contemporary conservatives angry about? Women making decisions about there health. Minorities being given opportunities to live better lives, the privileged having to share their privilege.

2) Pop culture is that exactly popular culture, it is the voice of the masses their expression of their views about the world. Conservatives despite their rhetoric are most concerned with the views of those in charge. The messages being expressed through conservative pop art does not reach out to the masses of people because those are not the views of the masses.

3) Corny. Conservative attempts at pop culture are corny because the “values” conservatives seek to uphold, are no longer ubiquitous to modern US culture. Conservatives seek to preserve or are in touch with values of eras long past (which never really existed as they remember) and no one wants to go back to because we would not consider youth culture before rock and roll worth participating in. The types of attitudes, behaviours and figures that encourage creative expression and serve as examples of the possibilities of popular culture are spurned by conservatives. Who do you want as your generational symbol of creativity and expression, Pat Boone and his descendant or Little Richard and his?

4) Independence. Conservatism despite its rhetoric is not interested in individuality that is different from its expectations. That means certain types of creativity (rebellious, outrageous, subversive) are not encouraged, and what follows isn that certain types of creativity don’t yield interesting results.
ipso facto Conservative pop culture is boring as shit.

UPDATE: I forgot to mention the arrogance and tone deafness that modern conservativism displays. Case in point to "Old School" Founding Fathers rapper at the Conservatism Political Action Convention. Check it at 1:53 where it becomes even too much for a Black Conservative to bear.

When the Party's Over, Turn Out the Light or "Look Whose Dancin, Now"

I am quite disappointed in the unexpected implosion of Herman Cain's campaign. I am completely convinced that Cain is taking every body for a ride. There is no way that he could possibly be serious about being POTUS. His already classic Uzbekistan answer gave you all the insight you need into who we are dealing with. This is no ordinary right wing maniac though the xenophobia is just the right temperature for a Republican presidential candidate. But Mr. Cain is doing something more that is betrayed by the slight smirk that gives him away on his ads.

Hermie Herm is straight clownin'! As George Clinton says, "[He] just funnin'!" He's not serious about being president, he is serious about shaking some money from the  conservative money tree plantation (plantation in its horticultural sense). That smile, the slight gleam in his eyes ("C'mon now you can't take me serious!") all are sayin' "You have to know that I am bullshitting!" Despite this, however, Hermie's attempt to paint lefty critiques of him as racist, despite high dis-approval ratings from Black Americans, is a bit "he doth protest too much." For the clear eyed observer that is hip to Herman's game, we see the oldest, Blackest figure in African Diasporic iconography. Herman Cain is channeling West African Folk figure Anansi. In the Ghanaian versions of the Anansi tales (the figure is prevalent throughout West Africa)  Anansi is a smaller creature compared to the other animals (Lion, Elephant, Monkey, etc) in the folkloric jungle. Anansi, a spider, has to use his wits to out smart and manipulate his physical superiors. Anansi is always scheming up on how to get food, position, advantage, etc for himself.

 Anansi's key characteristic was the ability to use his mark's weaknesses againstb them Usually nthese weaknesses were not apparent to the mark. Anansi was good at manipulating qualities such as pride, arrogance, vanity, naivete, etc. Though a selfish, cruel and often malice filled character, Anansi, could teach a lesson or two to serve his purposes.
 Our Mr. Cain is (consciously or unconsciously I have no idea) teaching a few lessons at the expense of the weaknesses of the Republican mind. Like the Deadly Sins of Roman Catholic dogma we can identify these Republican weaknesses as exploited by the right wing's most popular prankster.

• Vanity leads them to believe they have finally found out of 35 million African Americans the ONE smart enough to see the correctness of their beliefs. Sheer ignorance on the part of the other 34,999,999 is the only way to explain the disgust with which they hold the Republican Party.
• Ignorance or rather the celebration of ignorance which is becoming a hall mark of the party. Such a celebration allows Mr. Cain to display such shocking displays of non sense only becomes it affirms the "regular guy-ness" of him that ignorant Republicans thinks proves their normality. As Sensei George Carlin taught us, "If you have selfish, ignorant citizens, you're gonna get selfish, ignorant leaders."
• Insecurity is exposed in the election of Cain as the Republican Party's "Black Friend". If you are so desperate to not seem racist despite the comments of some of your most prominent voices that you drool over the one Black Guy that supports you, well nuff said. Herman Cain understands (see above smirk).
• Arrogance is obvious by the fact that your self righteous sense of entitlement to the Presidency leads you to be believe any old fool, as long as they are a Republican, can win the White House. As well your self righteousness is re-enforced by the belief that "real" Americans support your policies and will naturally vote for you (despite policy based polling to the contrary)

I could go on but the night is getting late and I have a lecture to write. But I must say I was soooo looking forward to Cain winning the Republican nomination and having him utter the "You fuckin' with me!" that rang around the world. At the least I know I can rest comfortably in the knowledge that Herman Cain will get his money and laugh all the way to yet another mansion paid for by Fox News, or The Heritage Foundation or Americans for Prosperity or the New York Post or . . . . . . .

(What does it say about popular images of Afri-US financial power, when I could not find a single image of a Black hand holding dollars on Google images?)