Gluyas Williams sold his first drawing to Life in 1911. He said,"They accepted the first one, and then waited about eight years before taking another." Maybe not so coincidentally, his appearances in Life increased noticibly around the time that Robert Benchley became an editor at the magazine in 1920. Benchley and Williams first met, and collaborated, at The Harvard Lampoon. It was a perfect marriage of writer and illustrator that would continue for decades. Williams illustrated all of Benchley's books and many of his stories. Benchley began to see himself in all of Williams' work. "There is only one drawback in having been Mr. Williams’s model for so many pictures. After years of capturing those particular facial characteristics of which my mother is so fond, he has quite unconsciously taken to putting me into all his drawings, commercial and otherwise, as the typical American Sap."
Williams attributed his early interest in becoming an artist to watching his older sister Mary at work. Using the pseudomym Kate Carew, she was "the first female caricaturist", known for her illustrated interviews with celebrities of the day such as Mark Twain and the Wright brothers. She also created the comic strip The Angel Child, which may also have given Gluyas an appreciation for sequential cartooning.
This post features Williams' earliest work for Life and are mostly representative of his take on the comic strip format. He would later create series that were primarily text pieces (such as his Senator Sounder character,) as well as pages depicting situations wordlessly and so well posed out that they practically animated. He also produced some astonishing full page single panel cartoons for Life and later for The New Yorker.
Richard Marschall wrote in The World Encyclopedia of Cartoons:
Seldom in the history of cartooning has there been an artist as much in command of his media as was Gluyas Williams. Technically his pen line was confident, attractive and reproducible, his figures comical but anatomically perfect, his use of perspective unerring. Conceptually his characters were strong, his choice of themes humorous, ironic and critically mature, his moods evocative and familiar. Williams seldom used tones but spotted blacks in seas of white and supple lines.
And he made it look so easy.