So far, my favorite is this one from 1900:
The story behind it is thus:
This city letter carrier posed for a humorous photograph with a young boy in his mailbag. After parcel post service was introduced in 1913, at least two children were sent by the service. With stamps attached to their clothing, the children rode with railway and city carriers to their destination. The Postmaster General quickly issued a regulation forbidding the sending of children in the mail after hearing of those examples.
Now playing: Rumbleseat - restless (hidden)