From 1929 to 1942, Ben Solowey led a dual life as a celebrated easel painter, while being one of the court artists to the Broadway kingdom. Commissioned by the New York Times and the Herald Tribune, Solowey defined an era in his striking charcoal portraits of the luminaries of the performing arts.

Unlike many artists in the field, he insisted on working from life, often visiting the theater during a rehearsal to delineate the performer either right on stage (frequently under a bare light bulb), or in an actor's dressing room. Because of performers' hectic schedules, Solowey sometimes had only minutes to capture the essence of his subject and the character they were portraying. Later performers took the opportunity to visit the Solowey studio on 5th Avenue in Greenwich Village where the artist could work undistracted.

He was one of the first artists to introduce halftone to newspaper reproduction. He chose charcoal because of its quick response to his hand, and preferred strong light to make an indelible mark on the page and reduce the possibility of error in reproduction.

To be drawn by Solowey was a sign that a performer had "arrived," and his portraits were eagerly awaited each week by both performers and newspaper readers.