With his brother Cole, he joined the Confederate Army during the American Civil War, eventually becoming a member of Quantrill's Raiders in 1864.

[1] After the war Jim tried his hand at various activities, including starting a horse ranch or deputy sheriff of Dallas County, Texas between 1870 and 1871.

It's uncertain how much time he spent with the gang, but he was present when his brother John was killed by Pinkertons in Roscoe, Missouri in 1874.

In 1954, Sheb Wooley played Younger in an episode of Jim Davis's syndicated western television series, Stories of the Century.

In the TV show Dr. Quinn, Medicine Woman, he was portrayed in the episode "Baby Outlaws" by Donnie Jeffcoat.