Born in Clapham, Surrey, the artist was educated first at Westminster School, before studying art and illustration at the Lambeth Art School. Later he was to attend Julian's Academy in Paris (1888-90) and to meet there other artists who also arrived in Cornwall around 1890.  Walter JEVONS and Lamorna BIRCH were two of these.

Tovey mentions Roller as one of the pioneers of St Ives Art (1889-1914) but it is not clear how long he remained in St Ives, after he became a founding member of the St Ives Arts Club.  His sending in and working addresses throughout his life were in London and Tadley, Berkshire. He married first in 1887 to Mary Margaret Halliday with whom he had two children, and secondly, after May's death in 1908, to Emily Kirk Craig.

A long-time friend of John Singer Sargent, he and his family were painted by the American artist (see jss gallery on-line for a portrait of Roller). A number of St Ives artists were part of Sargent's travelling circle, and met up from time to time as they moved around the colonies in England and abroad.

Roller was associated with the Burberry Company for more than 30 years, both as a friend of the family and as the primary illustrator of their sports attire and equipment. His work was featured in many national magazines, wherever Burberry advertised. He and Thomas Burberry had become acquainted through their mutual interest in horses, and both equestrian and sports settings were to feature largely in his painting. He also restored paintings for the RA at Burlington House, and for other museums in UK and abroad.

His military career gave him both prominence and many leadership roles. He fought in both the Boer War in South Africa, and in WWI in London and in France. He was a governor of several London hospitals, and until his death from 1928, an Honorary Life Governor of the Royal Berkshire Hospital.  In later life he continued to restore paintings, and he died while visiting in Salisbury, Wiltshire.