In the song, the little boy, who refers to himself as "Teddy Bear", gets on the CB radio and asks for somebody to talk to him. The narrator (also an over-the-road truck driver) answers "Teddy Bear's" call, and listens as the boy tells a heart-rending tale. Aside from his health and the father being deceased, his mother has been forced into the workplace to provide a meager income. Teddy Bear then says his wish had been to go for a ride in a semitractor trailer truck (he and his mother were to have joined the father on the road that summer) and is resigned to never getting to realize his dream.
The narrator is so taken by his tale that he decides to risk being late with his delivery to answer the boy's dream. However, when he arrives at the boy's home ("Jackson Street, 229"), numerous truck drivers — who also have been listening to Teddy Bear's call — are lined up at the boy's home, giving him rides in their trucks. The boy thoroughly enjoys his experience.
At the end of the day, the truckers take up a collection for Teddy Bear's mother. Later, his mother ("Mama Teddy Bear") goes on the air to express her gratitude, telling them Teddy Bear's dream had just come true. She offers a special prayer to the truckers for their act of kindness.
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