While a young white girl working in a Baltimore shoe store might not seem like a candidate for part of rock & roll history other than as a screaming audience member, Deborah Chessler was the subject of a 1991 article in Rolling Stone suggesting that she was indeed at the center of a defining moment in the genre. The year was 1948, and the then 18-year-old Chessler had a hobby that she was quite passionate about: songwriting. One of her tunes, "Tell Me So," had even been recorded by Savannah Churchill, but the resulting single release came and went faster than any of her shoe customers. Then a friend called Chessler to suggest she check out the sounds of a local vocal group called the Vibranaires. In fact, they were ready to sing for her, over the phone. The group was led by one Erlington Tilghman, who obviously was highly motivated to come up with his stage name, Sonny Til. The sound of the group was the sound Chessler had been hearing in her head. The rest, as they say, was history -- or more specifically, the history of doo wop.
Writer Greil Marcus, author of the aforementioned magazine article that was later included in a collection of his essays entitled Dustbin of History, presents Chessler as a young Jewish woman battling to promote an innovative style of black vocal music in a music industry in which racism and corruption battle for dominant vibe status. It is a portrait that is as vivid as the singing of Til and his fellow bandmembers is resonant. Chessler, struggling mightily, landed a contract for the group with Jerry Blaine, owner of the Jubilee label. It was Blaine who came up with the new name the group would hit big with, the Orioles. It was Chessler who came up with a smash hit for the group, "It's Too Soon to Know," composed in strict songwriting tradition on a scroll of toilet paper in the bathroom.
Blaine launched the It's a Natural imprint to release the song, an event that turned out to be somewhat revolutionary in terms of vocal groups and their audiences. While hitmakers of the day such as the Mills Brothers and Ink Spots sang for white audiences, the Orioles aimed their sound -- and, let it not be ever forgotten, the lyrical impressions of a young white woman -- squarely at the urban black audience. The song reached number one on the "race" charts and number 13 on the pop charts. "It's Too Soon to Know" has subsequently enjoyed a healthy life in cover versions, including recordings by Dinah Washington and Linda Ronstadt. Chessler was also in on the discovery of talented child performer Leslie Uggams, resulting in the following wise comments: "She knew just what to do with her hands, and how to stand and bow and talk. She was eight years old and more professional than a lot of people were at 30."