Using Willie Nelson Statue on T-shirt

Dear Rich, I am in the process of setting up a design company that will sell counter-culture t-shirts online. Additionally, my friends and I are creating a web comedy show where we insert commercials to advertise our prospective websites to drive traffic and increase sales. Both projects push boundaries due to the market we are trying to capture. (1) In one piece, I have photographed a toy dragon made by Schleich and applied my irreverent psychedelic pop technique. Others have photographed Star Wars, Barbie, Anime or GI Joe toys as apart of their artwork.I believe I can claim rights to fair use. Is that correct? (2) In another piece entitled Pothead says, I have used a portrait of George Washington that is labeled as public domain. I should be in the clear, but I want to make sure. (3) In a third piece, I have photographed a public statue of Willie Nelson that is just off the sidewalk in downtown Austin. Is this acceptable or is it a question of whether the statue is on public or private property? Can I claim fair use as well? Please repeat after us: I will not rely on fair use as a defense. As we have explained before, fair use -- no matter what you read -- is primarily a pay-to-play defense. You have to pay a lawyer to convince a judge it is fair use. The only exception is if your situation is on all fours with a previous fair use case. To get an idea if a case fits your needs, check out this summary of fair use cases prepared by the Dear Rich staff. (And check out the Fair Use site.) As for your specific questions, we've answered them, below.

1. The Dragon.  You should presume that the Schleich dragon is protected under copyright law. Your "irreverent psychedelic pop technique" may create a distinct derivative work, and maybe you could make a fair use argument (see above) but if Schleich saw your work and chose to hassle you, they could drag you into court and make you prove your fair use claim. (It's true that in one case, an artist was permitted to use Barbie dolls in his works but even if your facts are the same, keep in mind that the artist was dragged through a lengthy and expensive court proceeding.) Anyway, with so many public domain dragons, you may want to choose one of those instead?
2. George. A portrait of George Washington made during his life time -- for example, one of the George Stuart portraits -- is in the public domain. A portrait first published in the U.S. before 1923 is in the public domain. Works  published after 1922 may or may not be in the public domain (check this chart for more details).
3. Willie. The Willie Nelson statue is protected under copyright law. It doesn't matter whether the statue is viewable in public or private. We assume the sculptors own the rights (unless they transferred them to someone else) and if the copyright owners find out about your use (and care), they could hassle you. Again, a fair use argument is possible but see above.