[3] For six years Cressy worked with Denman Thompson in The Old Homestead theatre company, playing the part of Cy Prime.

They became one of the most popular and highly paid vaudeville acts of the period between the 1890s and 1920s, and toured internationally as well as within the U.S..[2] Cressy wrote all their comedic sketches, which included "Grasping an Opportunity", "A Village Lawyer", and "The Wyoming Whoop".

He was heavily involved in fund-raising drives in support of the war effort, and was one of the "Four Minute Men" appointed by U.S. President Woodrow Wilson to speak to audience on patriotic subjects.

In August 1918, he and Dayne traveled to France as part of the Overseas Theatre League, leading the first American company to entertain troops.

[4] Cressy and Dayne built a house for themselves at Blodgetts Landing, New Hampshire, where they entertained many leading show business personalities of the time and contributed to the local community.