Most makeup artists start working at retail for companies like MAC, Nars, Laura Mercier, Bobbi Brown and other brands that focus on makeup applications at the counter. Then they start freelancing on the side on unpaid test shoots for photographers, modeling agencies, etc or even by assisting established makeup artists. And eventually they get an agent when they have a good portfolio and start booking clients
You can start networking on sites like modelmayhem.com to meet photographers and models in your area you can work on test shoots with to help build up your portfolio.
You really need to be in either NY or LA if you want to work with celebrities.
A friend of mine who has been the on-tour makeup artist with people like Mary J Blige and Black Eyed Peas started at a MAC counter in NY. Another friend who now works on TV shows like American Idol in LA started on a Bobbi Brown counter.
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