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McCurdy spent most of the 1980s fronting several bands. The Men About Town (which included several members of Yipes!), Mankind, and The Confidentials all enjoyed minor success touring the Midwest. It was not until late in the eighties, when McCurdy decided to take tentative steps into performing solo, that he managed to find his real niche.
Performing initially for sparse audiences in small bars, he honed his act to what could be described as "interactive goofiness". For example, one of his most popular segments are his tributes to the 1980s and 1990s. These medleys, consisting largely of one-hit wonders from those respective decades, invoke a sort of call-and-response with the crowd, where McCurdy sings a line or two from each song, cueing the audience to continue that bit. This style quickly attracted a devoted cult following of fans, many of whom would (and still do) attend his shows on a weekly basis. McCurdy's act has also brought increased involvement of his sound and light man, Jim "Pipe Jim" Schafelburger, an entertaining aspect in its own right. Over time, the audiences became less sparse and the bars became less small, thanks mainly to word-of-mouth marketing.
He regularly tours the upper midwestern part of the United States with regular stops in Milwaukee, Madison, Chicago, Green Bay, and Minneapolis. His shows usually consist of just him and his guitar and include improvised interaction with the audience. While the majority of his audience is made up of a college-age crowd, McCurdy appeals to a large number of people of all ages. Performing well over 300 shows a year, his large catalog of original songs (over 600 and growing) covers a variety of topics such as lost loves, politics, family vacations, hair styles, the joys of Asian cuisine, the sex organs of long-dead French Emperors, how the world cannot live without Sex & Beer, and wishing to have a Monkey Paw. He even successfully makes humorous the mundane daily cycle of waking up, going to work, getting drunk, and going to sleep.
In 2008, he was asked by the Green Bay Packers to write a song to play in their stadium. Originally objecting because he did not like sports songs, he went on to write "I Love the Green and Gold," eventually making it into a music video starring himself and featuring Larry the Cable Guy. After the Packers won Super Bowl XLV, he wrote a follow-up song entitled "The Trophy Song."
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