The first entertainment business in Webster City was the Opera House that was built in 1870 by Walter C. Willson and operated by his brother, Sumler Willson. It was located on the second floor of the big brick building located at the northeast corner of the intersection of Des Moines and Second Street. The first floor was occupied by Crary's Hardware. One corner of the first floor housed first the Hamilton County Bank. Later this bank, called the Hamilton County State Bank moved across the street west to a huge new building. Its place was taken over by the small Webster City Savings Bank. The Willson Hotel was constructed at the southwest corner of this intersection. Sumler Willson was the first manager. After his death. The house was then managed by Willson's son Frank E. Willson for a period of several years. In the later years, from about 1912, the house was managed by W. B. Kearns.

The entrance to the Opera House was on the west side of the building. A wide stairway took the patrons upstairs. This building exists today, 1997, in essentially the same shape. The opera house was later divided into apartments. Musicals, plays, oratories, and other live performances were held here until after 1908 when other more accessible theaters came into existance. This was the major entertainment center in Webster City for a period of over 40 years.

Edward Overman of Des Moines took over management of the Opera House in 1907 from W. B. Kearns. Overman, who also operated the opera house in Fort Dodge, planned from 5 to 8 shows per season with changes planned on Wednesdays. "A 'Candy Matinee' was held on each Saturday afternoon for the benefit of the ladies and children, at which the candy will be distributed free," from the Freeman-Tribune dated Feb. 1, 1907.