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At 3-1/2, she appeared at the Palace Theater, as part of comedian Ted Healy's routine (Ted Healy would go on to put together "The Three Stooges."She soon became a child star. She appeared on "The Horn and Hardart Children's Hour," a radio program sponsored by Horn & Hardart's "Automat," a well-known restaurant chain, and worked with Milton Berle on his "Community Sing" radio program, using the name "Jolly Gillette" and playing the sponsor's "daughter" (the sponsor was Gillette Razors). She would ask to sing, he would tell her she couldn't, and she would remind him that her daddy was the sponsor, so he'd let her sing a current hit song.

She had a daily singing program of her own on radio station WMCA, "Arnold's Dinner Club." She also acted on radio series such as Death Valley Days.

Returning to radiok, she appeared as a guest singer on a Johnny Mercer variety series, leading to her being noticed by Frank Sinatra, who took her under his wing and put her in a regular spot on the CBS radio show that he hosted in the 1940s.

She co-starred on Sinatra's show for one year, and was also part of Sinatra's act at the Paramount Theater in 15 appearances there. She also appeared on her own and as a guest performer with such stars as Count Basie, Nat King Cole, and Danny Kaye.

Soon she got her own radio programs, first one called Teen Timers, and later the 13-episode The Eileen Barton Show. She also did some early television.