Hendricks began his singing career at the age of seven. He has said: "By the time I was 10, I was a local celebrity in Toledo. I had offers to go with Fats Waller when I was 12, and offers to go with Ted Lewis and be his shadow when I was 13. He had that song 'Me and My Shadow'. And he had this little Negro boy who was his shadow, that did everything he did. That was his act." The Tatum family lived on the same street as the Hendrickses. Jon Hendricks received his early musical training from piano prodigy Art Tatum, and the two of them began appearing together around town.