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English Wikipedia's image guidelines for living people stipulate that we can only use freely-licensed images of living people in articles, and our image use policy says that we can only use copyrighted images if no free alternative exists. This often means that editors themselves must take photographs of notable subjects, or that historical subjects have weird historical images rather than professional photos. Because of this, we occasionally end up with some unintentionally funny biographical photos. Here are some of the best.
All of these photos are either in use or were previously in use on English Wikipedia. Feel free to add more.