Born in Crawfordsville, Indiana, Holman lived as a child in Nappanee, Indiana, a town where six successful cartoonists lived when they were children. Holman's father died when he was young. He began drawing when he was 12 years old.
While working part-time at Nappanee's local five and dime store, he developed an interest in art as a career and sent away for the Landon School of Illustration and Cartooning correspondence course. Dropping out of high school, he was 15 when he moved with his mother to Chicago. There he took night courses at the Academy of Fine Arts and learned more about cartooning from Carl Ed.
In 1920, he held a job as a copy boy at the Chicago Tribune for six dollars a week. The position gave him the opportunity to hang out with the top Tribune cartoonists, including Sidney Smith, Harold Gray and E. C. Segar.
In Cleveland, he began working for the Newspaper Enterprise Association, which syndicated his short-lived animal strip, Billville Birds (1922). After three years with NEA and Scripps-Howard, he headed for New York, where he was a Herald Tribune staff artist and drew the child strip G. Whizz Jr. for the New York Herald Tribune Syndicate. He scored a success when he headed in a new direction, submitting his cartoons to a variety of different magazines, including Liberty, Redbook, Collier's and Life.