In the 1930s, the Great Depression caused chaos around the world. Unemployment in Australia reached a staggering 30%. Unemployed Sydney Harbour Bridge construction worker Harry E Kelly left his home, wife and four year old daughter to walk down the east coast of New South Wales, heading into the country looking for work ' only money pays the bills, as Harry had found out.
Fast forward to 2016. Harry's grandson, Jack B Kelly, born with the silver spoon and living a life of total luxury, is challenged to walk in the footsteps of his grandfather to get some idea of the pain that Harry went through in order to provide for himself and his family — and maybe appreciate the life he has inherited from his grandfather and father.
Leaving behind his wife Kate, Jack Kelly heads off as a modern-day swagman, taking work where he can find it. Along the way his sense of right and wrong will send him tumbling into a series of misadventures with local gangs, shifty cops, a hard-hitting rugby match and an unexpected travelling companion.