But each time she sang those songs, she would sing the chorus differently teaching and training herself to improvise. One night Billie was singing in a club when John Hammond, a young record producer came and heard her singing. He was amazed by her singing because he never heard a singer improvise the way Billie did. Because he was impressed and blown away by her singing he introduced her to Benny Goodman who then gave Billie, eighteen at the time, her first records "Your Mother's Son-In-Law" and "Riffin' the Scotch," the latter being her first hit. Because of her unique expressive and sorrowful and melonchiily singing style, she also got an opportunity to sing with well-known jazz pianist Teddy Wilson and other artists in 1935, recording many singles such as "What a Little Moonlight Can Do" and "Miss Brown to You.".
The next breakthrough for Billie's career came from the short Duke Ellington film in which she played the role of a rejected woman abused by her lover in Duke Ellington's short film Symphony in Black: A Rhapsody of Negro Life. In her scene, she sang the song "Saddest Tale . She felt that since her career was blossoming, she needed someone to help her organize burgeoning career so she turned to agent Joe Glazer who was also representing Louis Armstrong, Billie's idol. Glazer was a foul- mouth tough guy who also happened to be an ex member of the Al Capone mob. He wanted Billie to lose weight and take care of herself as well as clean up her image. Despite his hard and tough exterior, he was very supportive of Billie and made sure that she was taken care of. Billie's popularity around New York grew which allowed her to record more records because of her unique singing style as well as perform at the Apollo in Harlem as a regular. As a performer, Billie did not move or around a lot. She would simply stand in the spotlight, tilt her head backwards a little and snap her fingers, using her voice as a way to capture her audience.