The side project began in 1992 when Tom Scharpling of 18 Wheeler Records asked McCaughan to release some of his lo-fi four-track recordings; he obliged with the singles "Sandals with White Socks" and "Starter." Then in 1994 McCaughan released an entire Portastatic album, I Hope Your Heart Is Not Brittle, followed by the Scrapbook EP and more albums, 1995's Slow Note from a Sinking Ship and 1997's The Nature of Sap, which progressively became less lo-fi in nature. Released in 2000, the De Mel, de Melão EP paid homage to classic Brazilian artists like Caetano Veloso and Arnaldo Baptista. In 2001 McCaughan returned with Looking for Leonard, the score to a film written and directed by Superchunk fans Matt Bissonette and Steven Clark.

Around this time Superchunk went into semi-retirement and Portastatic became McCaughan's full-time group and a real band with revolving membership (though often including Superchunk'sJim Wilbur on drums). The full-length Summer of the Shark was released in 2003, followed by an album of covers and live songs (Autumn Was a Lark) later that same year. As Merge's profile in the indie world and beyond continued to grow (Arcade Fire and Spoon even reaching the upper reaches of the Billboard charts), so did the quality of Portastatic's output. Bright Ideas (2005) and Be Still Please (2006) are excellent albums that exhibit McCaughan's first-rate songwriting, and his 2006 soundtrack for Who Loves the Sun shows off his arranging and composing skills. In 2008 the band released a career-spanning collection of rarities and singles, Some Small History. ~ John Bush & Tim Sendra