Can you make a t-shirt of Jay-Z and sell it?

I just joined www.t-shirtforums.com - technical, business and marketing talk about the t-shirt making world. In a forum, someone asked the question: "Can you make a t-shirt of Jay-Z and sell it?" - pretty related to what I do. So I went to look for the answer, remembering about a court case with the "3 Stooges".

Thanks to Google research, I've found you can make t-shirts and sell portraits with your own artwork of famous people. But the rules are iffy and it depends how you do it. But know you can be sued for anything. The court case that defined the law is 2001's "Comedy III Productions v. Gary Saderup Inc". Gary Saderup sold "3 Stooges" charcoal portraits (he drew) on lithographs and t-shirts. But the family of the "3 Stooges" didn't like Saderup using the Stooges' likenesses. The artist lost the case:
Exercise Caution With Celebrity Images | Art Business News | Find Articles at BNET

In the case "Tiger Woods vs. Rick Rush". Rush, a famous sports artist, won the case.
Commentary: Legal ADvice - Tiger Woods sues artist for trademark | Daily Record and the Kansas City Daily News-Press | Find Articles at BNET

I think the differences in the two cases was how the products were marketed and how artistic/creative were they. Saderup's portraits bordered on realism so you could say he was selling the "3 Stooges" image. While Rush is a known sports artist, he's selling the "Rush" name, look & his artistic style and Tiger Woods was the subject matter.

The question may be "When is the artwork yours?" Shepard Fairey who did the famous Barack Obama (see image above) portrait is currently in litigation with the Associated Press for making his portrait based on an AP rights-owned photo. Ultimately I think a jury or judge has to decide if what you are doing is "artistic". Read both links above to get a better understanding of the issue. I believe you are artistic, Shep!