His first industry job was co-creating a series of shorts for the Independent Film Channel based on Greg the Bunny, a puppet character Milano also performs.

Milano exec-produced, wrote and performed on the series as characters Greg the Bunny and Warren the Ape, alongside co-stars Sarah Silverman, Seth Green, and Eugene Levy.

[citation needed] The relationship with Seth Green led to Milano's involvement as a writer and voice actor on Robot Chicken, Titan Maximum and Star Wars: Detours.

Milano has sold pilots including The Spaces, Dad Monster Hunter (also known as Shadowchasers), and worked on shows such as Crash & Bernstein (Director), and Star Wars: Detours (Writer/Actor).

In 2014, Milano and Eric Robles created Glitch Techs, an anime-inspired adventure comedy about a team of consumer electronic technicians that wrangle creatures and other phenomena caused by faulty video game technology.