Question 1: The statement is talking about a cowboy. Cowboys ride on horses. high ridding -est, is used as an adjective describing the cowboy. I'm just taking a guess here, but to ride high on a horse, you would probably have to be seated straight up with strong posture. So the statement could be using 'high ridding - est' as describing the cowboy as proud or confident? Question 2: No, you and I can be similar even though we don't 'look' like one another. We can be similar in our attitudes, our tastes, our preferences. You may mean 'look' as in 'appear', but that wouldn't be the same either. If we say something or person is similar, we usually mean that they are 'actually' similar. If we mean that they 'appear' or 'look' similar, we will say that there appears to be similarity or that they 'look' like one another. By saying 'look' its alluded that there isn't actually likeness but only the appearance of it.