Wigfield (2003) and The Colbert Report (2005–2014)
In 2003, Dinello co-wrote the novel Wigfield with Sedaris and Colbert, which they promoted by creating a traveling play. First pitched to Hyperion as a children's book about a worm searching for his identity. It later became a satirical story about a journalist, reporting on a small town on the verge of disappearing."
Since 2005 until the show's end in 2014, Dinello worked as a writer and supervising producer for The Colbert Report. He made some appearances as Tad, the building manager. The character often is berated by Colbert, who forces him to do dangerous things. In 2006 he helped Colbert with his speech at the White House Correspondents' Dinner, and together they revised it the night before the event. Of the speech's reception he commented: "I think that context gave it more weight than was intended. Had the president gone 'ha, ha, ha!' and slapped his knee and everyone laughed, I don't think there would be a lot of discussion about it." He also co-wrote alongside Colbert and other Report members, the book I Am America (And So Can You!) (2007), and its sequel, America Again (2012). He edited the audio version of the former.
In 2008, Dinello directed the Nickelodeon original movie Gym Teacher: The Movie, starring Christopher Meloni and Sedaris. That same year he had a bit part on Michel Gondry's Be Kind Rewind, where he plays a copyright lawyer, alongside Sigourney Weaver. Gondry asked Dinello directly to appear in the film. With Sedaris, Dinello co-wrote Simple Times: Crafts for Poor People, published in 2010. He can be seen with Sedaris in the "Mummified Hand" episode of the Science Channel show Oddities.
