As a child, Berry and his older brother Ananias (Nyas) began performing dance routines together.

[1]: 23 As a child, Berry and his older brother Ananais (Nyas) began touring the church circuit in Chicago, reciting poems by Paul Laurence Dunbar.

[1]: 23  The family soon moved to Denver, where Berry's younger brother Warren was born in 1922, and the duo began performing at carnivals.

[1]: 23 In the mid-1920s, the Berry family moved to Hollywood, Los Angeles, and James began performing at parties hosted by silent film stars.

[3] While working for Century, Berry starred in several Buddy Messinger-led projects, such as the 1924 films Low Bridge and Don't Fall.

[4][5] In the same year, he starred in Century's film Speed Boys alongside Spec O'Donnell and Arthur Trimble.

[16]: 18  In 1987, footage of Berry recreating his 1920s routines was featured in Dehn's documentary The Spirit Moves.