San Francisco artist (and recent Stanford graduate) Justine Lai is in the midst of an ongoing project to paint herself having sex with each of the Presidents of the United States in chronological order. She's currently up to Ulysses S. Grant (that's Ms. Lai with Martin Van Buren at the top of the post).
In an exerpt from her artist statement, Ms. Lai tells us:
I approach the spectacle of sex and politics with a certain playfulness. It would be easy to let the images slide into territory that's strictly pornographic—the lurid and hardcore, the predictably "controversial." One could also imagine a series preoccupied with wearing its "Fuck the Man" symbolism on its sleeve. But I wish to move beyond these things and make something playful and tender and maybe a little ambiguous, but exuberantly so. This, I feel, is the most humanizing act I can do.You can see the so far completed works here. They're somewhat more NSFW than the example above, but I think they accomplish, rather delightfully, Ms. Lai's stated goal. I look forward to her further travels toward the present (with a few notable exceptions).