Henry Lookout was born April 23, 1906 to Chief Fred and Julia Pryor Lookout. He attended school at Haskell where he witnessed the exhibition between John Levi and Jim Thorpe. He was married for 48 years to Dora Andrews McCarthy. Their marriage was arranged, which at that time was considered the β€œright way.” Their children were Edward, Randolph, Richard, Armeda, Anita, Mongrain and Yvonne.

Henry was the last ordained Roadman of the Native American Church. He was Roadman for the Lookout Native American Church for around 25 years. He served as Head Committee Man for the Pawhuska District through five Drum Keepers. Henry was also a 32ND degree Mason and a member of the Demolays. Both Henry and Dora Lookout were fluent Osage speakers.