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Guinan began his film pursuit as a producer at Chicago Access Network Television in 1992. He spent his first year writing, directing and performing in a weekly, half-hour sketch comedy called Possibly Blank, for which he occasionally wrote original music. In 1993 he directed his first short film, Johanna, a thirty-minute, black and white work shot on Super 8. Discovering he could use editing technology to mimic the visual characteristics of the 1920s and 30s films which had influenced him, he began developing a modern, dreamlike spin on commedia dell'arte in his work, creating the limited series Faces (1996), the access television movies Candy Town (1995), Alphabet Garden (1997), and various shorts including Accidents of Bread and Cheese (1998) and Missing Children (1998). His fifty-minute work, The Private Pennies of His Merry Dobbs (1998), was the "Innovative" category winner in the Alliance for Community Media's 1999 Hometown Video Festival Awards. In 1999, Guinan and his childhood friend Joshua Eckhardt formed the production company Chicago Avenue Films. Their first venture was the feature film Flipping the Whale (2001), which won Best Picture at the Lake Arrowhead International Film Festival in California, and the audience award at the Critical Mass Film Festival in Clinton, New York. Lennie and Jessie, a short extracted from the film, also showed at various film festivals, and aired on PBS' program Image Union. Their second feature, Teplitz: The Tyranny of Paradox was completed in 2008. In 2009, Guinan released Letters from Candy Town, a collection of original recordings of songs used in his prior TV and film work. The following year, he launched Candy Town, a live theatrical band which reflected the retro-influenced visual style of those films, and also featured Guinan's original music. The group was operational until 2016, and is documented in two concert films directed by Guinan.