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I'll express my opinion from a PR angle. Easiest is to give you an example. In my area, Raymond James, an investment company, is a highly respected and well-known corporation. The owner is a big art collector and his collection is hung in all the hallways of the corporate building. He's a patron of the Tampa Museum and very well known in the art community and the community in general. So, to have on your resume that you're hanging in his collection has some meaning in this area...to some people.
So, you can see in this example, some of the factors that might make an action such as this worthwhile. Without some PR potential, then you could be wasting your time.
Another angle on this is to find a corporation whose CEO is well-known, perhaps reaching retirement age. Try to get your portfolio submitted as a contender to paint his portrait for retirement. If you're chosen, of course, you want to work it so you get to be present at the presentation and have plenty of business cards handy, but give them out only when asked.
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