The song "Oh, Pretty Woman" was actually written and originally recorded by Roy Orbison in 1964. However, Johnny Cougar, who later changed his stage name to John Mellencamp, covered the song in the 1980s. The lyrics depict a man's fascination and admiration for a beautiful woman he sees walking down the street. He is captivated by her looks and expresses his disbelief that someone could be as attractive as her. As the song progresses, the man tries to catch the attention of the woman and engage in conversation with her, hoping for a connection. He asks her to stay with him, proclaiming that he will treat her right. However, the woman initially walks away, leaving the man feeling rejected. But to his surprise, she eventually turns back and walks towards him, giving him hope and excitement. The story of the song is mainly about a moment of attraction between two strangers. It explores the man's desire to get to know the pretty woman and his hope that she will reciprocate his feelings.