What about Banksy? While he was doing street art in the early 90s, his stencil work started to gain popularity around 2000. For me, his art not only reveals artistic talent, but also conveys a message as well. A lot of his work is aimed at social, political, or economic issues, most of which is very overt. But some of my favorite works of his are more subjective, like the stencil of the maid sweeping dust under a building or the street lines that lead up a building into a flower. The mystery that surrounds his identity made him all the more intriguing (to me, anyway). His distain for authority, and the authority's subsequent response, gives his work almost martyr status when it is covered up. It's a non-violent sticking it to the man. I'm certainly not well-versed enough in modern art to speak on any other artist whose work serves as any sort of commentary--or even if Banksy's work pales in comparison to someone else's. But for me, in terms of an artist who is readily identifiable for both the quality of his work and its message/impact, I think he serves as a good example.
Brokeback Mountain came in as a suggestion in the email and I'm wondering if it deserves to be on the list. I'm leaning yes, and I think there's an argument to be made that the movie was so well done, it did a lot to advance acceptance of gay relationships in the wider culture. Showing a gay relationship stripped of a lot of the stereotypes that make it safe on network TV or in other movies really did a lot to humanize that relationship and unlike Philadelphia (another great movie) it didn't get tied down trying to handle AIDS. I can't believe that I'm defending gay cowboys as an important piece of art but I know when I walked out of the theater after seeing Brokeback Mountain, I was emotionally crushed. And anything that emotionally powerful can't help but have an impact on those who see it.
Kanye West. The persona and his discography. He is the last decade in a nutshell: outward brazenness coating deep-seated insecurity wrapped in a shell of manic expression. He's this amorphous blob of media-driven public opinion living in a synthetic pseudo-reality that I'm not sure even he fully understands. It's impossible for the average person to determine what about the man is genuine, and what is just another contribution to the celebrity/reality TV/music mogul/satirist hybrid meatsack that constitutes West. We've decided that we want to celebrate and vilify in the same breath, and no one provides a flood of contradictory emotions quite as effectively as he does. Listen to Fantasy. The album is crazy. I don't mean "crazy good" or "crazy fun". It's literally fucking crazy. It's the musical interpretation of a mind that cannot ground itself in any sort of objective truth and does not care. He is the living, breathing sense of uncertainty that we have created for ourselves.