Raleigh became the observer of the Immortal Richard Sharkey in 1656. Sharkey lost his head to Walter Reinhardt in 1662, and he needed an new assignment. In 1663 he became part of Walter Graham's travelling theatre group. He observed him and Duncan MacLeod who was also part of the group untill 1665. MacLeod left the group and Raleigh would follow him till 1675. From 1676 to 1686 he observed Robert Montague. After those years he retired.