John Michael Skipper was born at Norwich, England in 1815. Skipper was an intelligent, vivacious solicitor and an imaginative artist. Although the practice of Law was Skipper's primary occupation, he is remembered predominantly as an artist who documented the character of early colonial South Australia.

JM Skipper was the eldest son of John and Jane Skipper. Skipper received his schooling at Norwich Grammar School, where he followed in the footsteps of his father and studied to be a Solicitor, he also excelled in classics and modern languages. Skipper developed a passion for art, which was greatly encouraged by his Mother’s brother, James Stark, an accomplished landscape painter and member of the Norwich School of Landscape Painting.

Skipper postponed his studies in 1833 and became a midshipman on 'Sherbourne', an armed vessel of the East India Company bound for Calcutta. After returning to Norwich and somewhat keen for new horizons, Skipper arranged for himself to be articled as a clerk to Charles Mann, the new Advocate-General for South Australia. He immediately migrated to the small colony of Adelaide, South Australia, and arrived on the 'Africaine', at Holdfast Bay on 6 November 1836. While onboard the ‘Africaine’, Skipper created a series of Sketches and met his future wife Frances Amelia, daughter of Robert and Mary Thomas; he married Frances Amelia three years later on 28 December 1839.

Skipper was associated with the Supreme Court partners Mann and EC Gwynne, from 1836 to 1843. During this association, in 1940, Skipper was admitted to the bar as an attorney and proctor of the South Australian Supreme Court, he practised from 1843 to 1851. Caught up in the excitement of 1851, Skipper ventured out to the Victorian goldfields, returning a year later with a wealth of sketches, rather than a fortune in gold. Skipper returned the same year to work at Port Adelaide as Clerk of the Court, where he stayed until his retirement in 1872.

Skipper's artistic style is romantic and imaginative while demonstrating a keen observation of nature. Skipper had a sharp awareness of his surroundings and regularly recorded the landscape, flora, and fauna. He also attended and recorded events, which captured the public’s attention. An example of which is the visit of the infamous Lola Montez, an Irish born dancer and actress, and quite possibly the most famous woman of the Victorian Era, aside from the Queen herself. Skipper's Paintings and sketches have become historic moments in South Australian History, icons of the colonial past. Skipper also painted and sketched the everyday, the streets, the homes, the people, even his own family home. Skipper also illustrated an amount of notes and records from the explorer Charles Sturt’s expeditions, devising the sketches from his vivid imagination, observations and detailed descriptions and comments provided by the explorer. Skipper was a constant illustrator, compulsively drawing and recording his own observations, filling any blank space in his own Journals and South Australian almanacs with sketches, comments and recollections.

After his retirement, Skipper lived the remainder of his life on a small pension farm at Kent Town. Despite the constant presence of law throughout his life, he died without having made a will on the 7th of December 1883. JM Skipper married twice in his life, once to Frances Amelia Thomas, and after her death, he married her younger sister Mary. Skipper was survived by seven children, to Frances, he was succeeded by four daughters and a son who are all pictured in 'Skipper Family at Islington', and to Mary he was succeeded by a further two sons.