For my brother's wedding, he wanted to have name badges for all the guests featuring a caricature of him and his then-fiance-now-wife on them.
I did feel I could get away with a bit of artistic licence when it came to my brother (also it's easier to get away with drawing someone with a big nose if they don't actually have one), but I felt I needed to be a bit kinder with the depiction of his wife. I think I kept a nice consistency between the two illustrations and they were well received. It's easy to get honest opinion on things when no one knows who did them. Also it's easy to get a positive opinion when people are drunk.
Here's an action shot of the 150 badges made.