He began taking vocal lessons in 1924 and in 1926 moved to Chicago with plans to continue his voice studies.
[4] In January 1946, O'Halloran became the master of ceremonies on Wake Up and Smile, a Saturday morning program on the ABC radio network.
While he worked at WCFL, he was one of two speakers on Biographies in Bronze, an educational series about people from history, especially those who explored and settled North America.
[4] At WLW, he was host of a weekday morning program that included children's songs and riddles and "tidy-up time", during which he encouraged young listeners to pick up their clothes and toys.
[10] Besides his work on radio, O'Halloran toured the Eastern United States with a barn dance production After he went to Cincinnati, he made personal appearances with the Boone County Jamboree.