Crutchfield was born in Melbourne, but attended high school in the coastal city of Warrnambool.
He was a popular and high-profile councillor, and subsequently served as the city's mayor from 2000 to 2001.
Crutchfield remained on the council after losing the mayoralty, and contested Labor Party preselection for the state seat of South Barwon, which was considered a safe seat for the conservative Liberal Party, and had never been won by Labor before in its history.
Aided considerably by a statewide landslide victory for Labor, Crutchfield defeated long-serving incumbent Alister Paterson in the 2002 state election, and took up his seat in parliament.
He is an avid Geelong Cats supporter and a former coach and captain of the South Barwon Football Club.