In 1912, at the age of twenty four, he resigned[1] from his job and, with the financial assistance of his brother, travelled to London to study at Saint Martin's School of Art.

Originally a satire, featuring the characters "Mr Pott" and "Whalesteeth", designed as a means of offering political comment, it was quickly converted into a domestic humour strip.

[4] In the 29 July 1933 issue of Smith's Weekly, a Cross cartoon featured two men who had been working on top of a building construction.

His mate, to save himself, has grabbed the trousers of the other, yanking them down over his ankles and, looking directly upwards, is convulsed with laughter, while the other implores: "For gorsake, stop laughing: this is serious!".

Short-run series he devised included: Things That Make Stan Cross (political and economic criticism), Places We Have Never Visited (law courts, Parliament, the players' room at a test cricket match, etc.

[3] Towards the end of 1939, Smith's Weekly was in financial trouble and Cross was induced by Keith Murdoch to join the Melbourne Herald.

[4] Over the next thirty years in newspapers throughout Australia, New Zealand and Fiji, and in eighteen annual comic books (c.1943–60), readers were able to enjoy the extraordinary, knock-about adventures and lifestyle of Private Wally Higgins, Major Winks, Pudden Bensen, and a company of comedy players—in the army in World War II and, afterwards, on their North Queensland sugarcane plantation.

[3][7] Their annual trophy "The Stanley" was named for him, with the award taking the shape of the figures in his classic cartoon, "For gorsake, stop laughing: this is serious".

He painted watercolours and there is some speculation that Cross and George Finey held the first exhibition at David Jones Art Gallery.

[2] In 1970, he retired from the Melbourne Herald and joined his family at Armidale, New South Wales, where he died on 16 June 1977 at the age of eighty-eight.