I think Will Rogers was trying to make a point. I think he meant to say to the rest of us that everybody deserves respect and their opinions count too. I just can't believe he liked everybody he met. It isn't humanly possible since we all have bad days.
Now Jesus loved everybody but I don't think he was a big fan of Pontius Pilate. It is more likely he was setting an example for the rest of us to follow and he knew that forgiving even one's enemies is better than harboring a grudge because that's self-destructive. The idea that it's easier for a poor man to get into heaven than a rich one through the eye of a needle implies that having little does not distract you from the goal of doing good. Having so much you think it needs protecting, makes you greedy and less likely to selflessly do the right thing.
Will Rogers was a political humorist. You could say he was an early stand-up comedian but ran more one-man commentator on the events of his day. He wrote many newspaper columns and was a movie star in both silent and early talking movies. He died in a small plane accident in 1935. Although he is credited with the statement, I've heard he used to append it with a "yet." I have also heard stories others have told who refute Will's ability to like everybody. Once when invited to join a newsman's chat he told his host to "get lost kid."
One of my greatest regrets in life is that I cannot say I never met a man I didn't like. Being a shy person, I find myself avoiding situations where I might lose my inhibitions and start liking people more. At least knowing I am doing that is a step in the right direction.