Bowlen was born in Prairie du Chien, Wisconsin, the son of Arvella (née Woods) and Paul Dennis Bowlen, who became a millionaire in the Canadian oil business, founding Regent Drilling as a wildcatter. Bowlen attended the University of Oklahoma and earned degrees in business (1965) and law (1968). The younger Bowlen became wealthy in his own right by becoming a successful lawyer in Edmonton, Alberta. He also worked as an executive for his father's company and as a real estate developer and had major investments in the mining industry.