In the mid 1990s, Brooke worked selling pizza in Tucson, Arizona with future bandmates Ben Bridwell and Jenn Champion. In 1997 the trio moved to Olympia, Washington for a year before becoming bored with that city and moving to Seattle. Brooke and Champion had met in Tucson aged fifteen and had briefly both lived in Michigan.
In Seattle, Brooke and Champion formed Carissa's Wierd, who released three studio albums, the first two on Bridwell's Brown Records label. The band broke up in 2003, since then three compilation albums have been released. Carissa's Wierd reformed for a one off show in Seattle on July 9, 2010.
In July 2010, Brooke announced that he and Jenn Champion had bought the rights to Carissa's Wierd's back catalogue from Sad Robot Records. He said, "Me and Jenn have been working for a while to buy back the rights to all of our records and we finally were able to get them all back." This should allow all of Carissa's Wierd's albums to be re-released soon.

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