John Henry, a freed slave, happens across a railroad building project. An entire crew of freed slaves has been promised land if they can finish by deadline, but fail when they're exhausted and unable to continue. John, though, has the strength of ten men, and revitalizes all of them. But despair sets in again when the railroad sends a steam hammer to replace the crew and burns the contract. John proposes a challenge: man against machine. After a heroic effort, including a tunnel through solid rock by swinging two hammers at once, John wins the challenge, but also collapses in his wife Polly's arms, much to her disappointment. She's recounting this whole story to their young son, to explain why his father was so great.
- Alfre Woodard as Polly / Narrator
- Carrie Harrington as Polly's singing voice
- Geoffrey Jones as John Henry
- Tim Hodge as Mactavish
- David Murray as Thomas
Directed by Mark Henn, the short tried to go for the visual style of 50s and 60s Disney shorts such as fellow tall tale adaptation Paul Bunyan as well as a Mary Blair inspired patchwork quilt opening. It would receive a DVD release in 2002 on the Disney's American Legends DVD, though in a fullscreen presentation rather than the widescreen format it was produced in. However, it was made available on its original widescreen-produced format in 2015 on the Walt Disney Animation Studios Short Films Collection Blu-Ray and DVD.