[3] Jolley stood as the Green Party of Canada's candidate in the riding of Bruce-Grey-Owen Sound in the 2006 Federal Election.

[2] In the 2007 provincial election, Jolley was the Green Party's candidate in Bruce—Grey—Owen Sound and came in second place with more than 33 per cent of the vote, giving Jolley the best finish of any Green Party candidate in a Canadian federal or provincial election at that time.

[5] Jolley highlighted his fiscally-conservative, socially-liberal attitudes, praising portions of the Progressive Conservative platform, calling for local solutions to issues, and attacking rigid partisanship.

Jolley had been personally investigating a spate of thefts of high-priced bicycles in Owen Sound and mistakenly found himself on the property of two local residents.

Jolley attempted to personally apologize for the incident, but the homeowners opted to pursue legal action.