After Comets on Fire played Auckland, Utrillo Kushner met one of his idols, the legendary DIY producer and songwriter Chris Knox. The following day Knox invited Kushner and his bandmates over to his house for conversation and beers. The afternoon was spent in the kitchen (Knox was baking a cake for The Clean's Bangers and Mash anniversary tour) drinking while Knox spun stories of the New Zealand music underground of yore. From this experience, Kushner conceived of the initial idea for the second Colossal Yes album.

Inspired by the Kiwi indie-pop formulas of Tall Dwarfs, The Clean, and The Verlaines, Kushner set out to write his own songs using piano as the main instrument. It was a reawakening of the pop aesthetic done Piano Man style. Recording of the basic tracks started in the summer of 2007 with Kelley Stoltz producing and Kevin Ink engineering. Songs were then fine-tuned over a series of nighttime and weekend sessions with Matt Waters in early 2008. Finally, they were mixed with Ben Chasny (Six Organs of Admittance) and Waters almost a year from the starting point. The end result is unique yet similar to the epic pop bands of the past. Charlemagne's Big Thaw combines simple melodies and basic structures with lyrical territories such as expired youth, grand betrayals, overdrawn faculties, and dissolving empires. In this regard, Kushner pays respect to songwriters like Robyn Hitchcock, Dan Bejar of Destroyer, and Alex Chilton while also incorporating the honesty of Graham Nash's Songs for Beginners, the romanticism of Nikki Sudden's Waiting on Egypt, and the sonic merriment of Thunderclap Newman's Hollywood Dream.