Whitelaw Hamilton spent his early career in business in Glasgow, but was also an amateur painter. He became an increasingly active among the Glasgow Boys group and painted with James Guthrie, Joseph Crawhall and E A Walton at Cockburnspath, Berwickshire in 1883. Around 1887 he decided to take up painting professionally and moved to Paris to study in the studios of Dagnan-Bouveret and Aimé Morot. On his return to Scotland, he painted predominantly naturalistic landscapes around the Berwickshire coast and his native Helensburgh, where his home was a favourite meeting place for the Glasgow Boys. Whitelaw Hamilton later exhibited internationally and was influential in organising exhibitions abroad, and promoting the work of Scottish artists internationally.