Between 1886 and 1893 he published nearly fifty songs, including "The Letter That Never Came" (1886), "I Believe It for My Mother Told Me So" (1887), and "The Pardon that Came Too Late" (1891). These early successes may have encouraged Dresser to pursue songwriting rather than performing. In addition, he may have realized that publishing music would provide even more financial success than composing or performing. By 1888 Dresser believed his songs would have popular appeal to a national audience. He stopped selling his songs through midwestern publishers, moved to New York City, and turned to Willis Woodward and Company, a New York City music publisher located in the area that later became known as Tin Pan Alley. Woodward and Company printed "nearly three dozen" of Dresser's songs. Dresser continued traveling with "The Two Johns" show until the end of 1889 and composed music after the show season ended. In 1890 Dresser began performing in "A Tin Soldier". Managed by Frank McKee, the Charles Hale Hoyt production was in its fourth season when Dresser joined the twelve-member cast. Dresser, who had been large since his youth and weighed nearly , performed as a jolly plumber in the nationally acclaimed show. "Days Gone By" and other Dresser songs were included in the show. He began to have a dispute with Hoyt over the use of his songs, and Hoyt's refusal to acknowledge him as the composer. Dresser left the act in April 1891 and traveled the country performing in "The Danger Signal". Dresser also began to sell his songs to other acts for use in their performances. After they made his songs famous, Dresser would then publish the sheet music and sell them through the firms on Tin Pan Alley. Dresser's songs and acts were usually sad and melodramatic, but a few were romantic and silly. At the height of the Panic of 1893, Dresser formed a partnership with Frederick Haviland and Patrick Howley as a silent partner in Howley, Haviland and Company. The New York City firm published Dresser's works, while he recruited new songwriters and encouraged singers to perform the company's songs. Dresser stopped traveling and performing during the summer so he could focus on composing music and promoting the new company. In 1894 he invited his younger brother Theodore to join him in New York. Theodore went to work for Howley, Haviland and Company as editor of the firm's trade journal, "Ev'ry Month", which promoted their newest songs.