Q: Can I print Bob Ross on a shirt? I have a direct to garment Printer
A: **Using Bob Ross's Paintings**
Bob Ross was born in 1942 and presumably began painting some time before hosting The Joy of Painting, which first went on the air in 1983. I'll assume you're talking about using paintings created on his famous show.
If Bob Ross's work was published after January 1, 1978, it receives the following terms of protection:
Individually authored works: Life of author + 70 years;
Joint works: Life of last surviving author + 70 years;
Works made for hire: Shorter of 95 years from publication, or 120 years from creation.
According to Wikipedia, Bob Ross died in 1995. So, no matter what the nature of the authorship of his work, it still protected by U.S. Copyright law. Ownership of the copyright in his work is likely held by the heirs of his estate or Bob Ross Inc. You would need permission/a license to use images created by Bob Ross, otherwise, you could be liable for copyright infringement.
**Using Images of Bob Ross Himself and Bob Ross's Name**
If you're using a photograph of Bob Ross, the photographer owns the copyright in that image. So, you face the same issues described above for copyright infringement and requiring a license to use an image created by someone else. But, let's assume that you have a photograph of Bob Ross that you took yourself, or you obtained a license to a photograph. States have their own laws regarding publicity rights or misappropriation of likeness, and your use of his image, especially in commerce, is likely to give rise to legal liability. The major issue being, it's likely that consumers will believe your product is endorsed by Bob Ross (Inc.).
Additionally, people can obtain trademarks in their own names, signatures, physical likeness, voice, and other identifying characteristics. See Trademark Manual of Examining Procedure Section 1301.02(b) for more information on trademarking a personal name. I haven't done any research into whether there is a trademark or service mark for Bob Ross, I am just raising the possibility that you could also face legal liability for trademark infringement and other associated causes of action.
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