Traveling as part of the Windy City Blenders, she learned drag from members of the Chicago Kings while on their first tour in Ireland. One night, Tamale dressed in drag for the first time and went out on the streets with the rest of the troupe. It was a thrilling experience and she began to play with masculinity in her performances. Binding her breasts and wearing a “packie” (a more realistic replacement of the commonly used sock), she took on various characters, performing masculinity with tongue-in-cheek pieces. Combining sketch, improv, and drag, Tamale and Sayjal Joshi created Redneck Advice with Cody and Jeb. They were invited to perform at Second City’s UP Theater, Laugh Factory Chicago, Chicago Sketch Festival, and other gigs.