For the past 20 years, Jeff Robin has been making these cutouts along with traditional paintings. Cutout paintings allow freedom in composition and the negative space is truly cut away. In a traditional sense, this is cheating, but they look cool and are fun to paint. The silly shading, attention to needless detail and the lack of specificity to reality are aspects of informality and carelessness that one gravitates to because there is no pretension left.
These are genre paintings, rock n' roll iconography, and the only way Jeff could see doing these without being ironic or corny was to be silly and fun the equivalent to dancing like you don't care who is watching.