A: Perhaps. Privacy and publicity rights protect personal interests of the people who are represented in, or by, the work so in this case the artists you mentioned above. There are a few states currently that have statutes where the right of publicity survives the death of the person and protection could be as long as 100 years. The other area you would need to consider is where you are getting the images of these celebrities to place on your t-shirt and if you are violating the copyright of the image owner. I suggest you contact an IP attorney to examine your own particular case to determine if you are violating any rights.
A: By virtue of the fact that you have a business partner, you won’t be able to operate as a sole proprietor. It would be a partnership. The decision to operate as an LLC, partnership or a corporation will vary depending on the type of business, growth trajectory of the business, such as if you ever plan on bringing in outside investors etc. You and your partner will be best served by contacting an attorney to guide you with this process, as well as assist you in drafting either an operating agreement, bylaw or partnership agreement that include critical partnerships terms such as buyout of one partner etc.
A: A trademark Owner may file a request to reinstate a registration if the registration was cancelled or expired for failure to file a section 8 affidavit, trademark renewal or response if they can provide proof that the cancellation was due to USPTO error or that the registrant didn’t receive the post-registration action.