He composed his best-known song "I Wonder Who's Kissing Her Now" in 1909, with lyrics by Will M. Hough and Frank R. Adams, selling the song to Joseph E. Howard. When the song unexpectedly became a hit, Howard presented it as his own work for several years.
Orlob became a prolific composer for Broadway. Among his works were the short run of Corianton: An Aztec Lovestory, a work pushed through by Orestes U. Bean's salesmanship and based on the novel Corianton by B. H. Roberts. His most successful show was Listen Lester, which ran for 272 performances between 1918 and 1919. It included the song "Waiting," recorded by several artists of that era.
In 1939 Orlob produced the film ...One Third of a Nation.... Returning to Broadway musicals, in 1943 he produced Hairpin Harmony which would become a legendary flop, closing after three performances. He continued to write songs as well as a symphonic work, Recreation.
In 1947 "I Wonder Who's Kissing Her Now" was used as the title song of a movie about Joe Howard, leading to renewed popularity for the song. At this time Orlob brought suit to declare himself the composer, eventually reaching an out-of-court settlement with Howard for the two of them to receive joint credit. Orlob did not claim royalties.
- American Musical Theatre: A Chronicle by Gerald Martin Bordman and Richard Norton, page 293
- Listen, Lester at Internet Broadway Database accessed March 28, 2016
- Discography of American Historical Recordings, s.v. "Harold Orlob (composer)," accessed March 28, 2016
- The Complete Book of 1940s Broadway Musicals by Dan Dietz, pages 190-192
- The Myth of Joe Howard Lingers in a Familiar Air by Philip Benjamin, New York Times, June 4, 1961