Luckily for Wright, at the time he wrote laws did not require the disclaimer that all characters were fictitious and any resemblance to people, living or dead, was purely coincidental. Many of his characters were based on living people; many of those people were friends. And many times, he was one of his own characters. In The Shepherd of the Hills, he is the shepherd, the preacher who has gone to find peace in the healing powers of the woods and hills and streams, just as Wright returned, time and time again, to nature for spiritual and physical renewal.

Wright's characters may have been based on actual people, but they were bigger than life and he was criticized for his artificiality in characterization. Young Matt is a giant of a man, a perfect physical specimen, intelligent, fearless, frank, kind, gentle and honest. Sammy Lane is even more splendid, for she strives to become a better person through learning the finer graces of life, but never forgets that inner qualities alone determine whether or not a woman is a lady. Through these and lesser characters, Wright develops the principle of manhood and womanhood, that being a man or lady comes from quality of character. Both should be thoughtful, sympathetic, fun-loving and always desire to help others.

Wright characterizes Sammy as "not to be described." Although he details her womanly appearance, it can not capture the real woman. He lets another character reveal her magnificence: "That gal o' Jim Lane's jest plumb fills th' whole house. What! An' when she comes a-ridin' up t' th' office on that brown pony o' hern, I'll be dad-burned if she don't pretty nigh fill th' whole outdoors, ba thundas!"

It is not difficult to see the color of the hats in Wright's novel. The "bad guys" are drunken, slovenly, dirty, sweaty, rude and boastful. The "good guys" are always concerned for the other person. They may be dusty and grimy from working in the field, but they always have clear eyes and walk with a sure step.