Wiki has a guideline to use recent photos for living figures, and will use more hey-day pictures after the person passes. Compare the pictures for William Shatn

Wiki has a guideline to use recent photos for living figures, and will use more hey-day pictures after the person passes. Compare the pictures for William Shatner and Leonard Nimoy. I think this is a good balance - it acknowledges people change, and sets your expectations should you see the person on the news or something, and then later they're reflected as they were best known. Note that most of your good examples are deceased and most of your bad ones are living. I learned this when Elizabeth II passed, and her photo was updated very quickly to a much older portrait.