The property initially opened as the Dixie Bar in the 1940s.
The Skyline opened as a casino on the property on October 1, 1964, but closed the following year.
The Skyline reopened on October 1, 1974, and has been renovated numerous times since then, with a 51-room hotel structure opening in June 2017.
In April 1952, Dorothy Dukett committed suicide through a gunshot wound while conversing with her husband.
The suicide occurred in the Duketts' home: a room at a motel that was a part of the Dixie Bar at the time.
The Cooks had no storage space for their many books and chose to store them on a book shelf in the bar.
Customers to the bar were allowed to borrow the books.
Many people who enjoyed the service began donating their own books.
The bar soon became known as the only place in Pittman where people could purchase or borrow books.
The Henderson Home News noted that "Pittman may well be the only town in the United States where the only library is located in one of the local taverns." By February 1957, the bar contained nearly 400 books.
Customers suggested that a small fee be charged for the books, with the money being donated to charity.
The fee was implemented and the money was ultimately used to purchase playground equipment for local children.