As a brother duo who started off in Toronto by renting a four-track and recording covers of James Brown and George Thorogood, the duo performed in various groups as teenagers. In 1987, known as the Synthetics, the brothers edged out Alanis Morissette for the Canadian National Exhibition National Rising Star Award. In 1992, renamed as Van Creeggan and then later to the Brothers Creeggan, the group's first gig was in Halifax, Nova Scotia, opening for Bob Wiseman. In 1993, the band entered the studio to record its self-titled debut album. As well as being members of Barenaked Ladies, the duo took time to continue as a band, releasing Brothers Creeggan, Vol. 2 in 1996. During this time, Andrew Creeggan left Barenaked Ladies to concentrate on songwriting, entering a five-year musical composition degree at McGill University. In 2000, the Brothers Creeggan added a third member, drummer Ian McLauchlan. More touring ensued and the group's fourth album, Sleepyhead, was released in May 2002. The album featured appearances by Sarah Harmer and Ed Robertson. The Brothers Creeggan have been compared to various folk-rock groups, as well as everyone from Neil Young to the Kingston Trio.