May Irwin (1862–1938) was an American singer and actress, celebrated as one of the first stars of vaudeville and early American musical theatre. She was a prominent figure in the late 19th and early 20th centuries, known for her comedic style and powerful voice. Irwin's genre primarily encompassed vaudeville, music hall, and early popular songs. One of her most notable works is "The Widow Jones," a hit song from 1896 that showcased her distinctive singing style and comedic timing. She is perhaps best remembered for her rendition of "The Bully Song," which became immensely popular. Irwin's impact on music and performance was significant; she was among the first to successfully transition from stage to film, appearing in early silent films, including a notable role in Thomas Edison's film adaptation of "The Kiss" (1896), which is one of the first films to feature a kiss on screen. Her contributions helped pave the way for future performers in both theatre and film, influencing the development of American entertainment and the integration of music into popular culture. Irwin's legacy endures as a pioneer who brought a unique blend of humor and song to the stage.