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Jim was born in Youngstown, Ohio, and later moved to New Orleans where he was worked on Mardi Gras floats and as a door-to-salesman, he then moved to California where he worked odd jobs before he got into voice acting. Cummings is known for his ability to mimic Sterling Holloway's high voice.
- Cummings is the third person to voice Winnie the Pooh and Kaa, after Sterling Holloway and Hal Smith.
- Not related to fellow voice actors Brian Cummings or Todd Cummings.