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.