Every night on CBS’s The Late Show with Stephen Colbert, millions of viewers tune in for Stephen Colbert’s razor-sharp political monologues and biting satire. But working directly behind the curtain—as he has for nearly forty years—is Colbert’s closest creative lieutenant, supervising producer, and frequent on-air foil: Paul Dinello.
Before they were dominating late-night ratings, however, Stephen Colbert and Paul Dinello shared one of the most famous mutual-dislike stories in comedy history.
The 1988 Touring Bus: An Unlikely Meeting
In 1988, both men joined The Second City’s touring company. Dinello was a streetwise Chicago native who drove a cab to pay rent and had honed his chops in improv basements. Colbert was a serious, deeply intellectual Northwestern University graduate who wore ties and took acting theory with utmost solemnity.
Their initial impressions were disastrous: * Colbert on Dinello: “I thought he was pretty much an illiterate dolt… a semi-literate thug.” * Dinello on Colbert: “I thought he was an incredibly self-important, pretentious guy whose tie was wrapped way too tight.”
The ice finally broke when Second City management assigned the pair to write a custom corporate Christmas show for McDonald’s franchise employees. Locked in an office together, the two realized they shared an identical sense of the absurd. Within weeks, they had developed an unspoken rhythm that made them virtually inseparable.
The Faculty Lounge: Strangers with Candy
In 1999, along with Amy Sedaris and Mitch Rouse, they debuted Strangers with Candy on Comedy Central. The show’s most celebrated running dynamic was the closeted, high-strung romantic affair between history teacher Mr. Chuck Noblet (Colbert) and art teacher Mr. Geoffrey Jellineck (Dinello).
Playing their scenes with the deadpan melodrama of a 1950s Douglas Sirk soap opera, Colbert and Dinello turned faculty-lounge domestic disputes into high-wire satirical art. Their characters’ petty jealousies, vanity, and complete disregard for their students set a new standard for subversive television writing.
The Colbert Report: The Brain Trust and “Tad”
When Stephen Colbert launched The Colbert Report in October 2005, he brought Dinello on as supervising producer and core writer. Dinello helped shape the show’s signature satirical voice, parodying right-wing cable commentators with uncompromising commitment.
On camera, Dinello played Tad, the terrified studio building manager whom Colbert’s egomaniacal character routinely forced into hazardous physical stunts.
Most historically, Dinello was Colbert’s key collaborator for the 2006 White House Correspondents’ Dinner. On the eve of the historic performance, Colbert and Dinello sat in a Washington hotel room until dawn, refining jokes that would deliver one of the most blistering, unforgettable satires ever delivered directly to a sitting American president.
The Late Show on CBS
When Colbert took over The Late Show from David Letterman in September 2015, Dinello moved to the Ed Sullivan Theater as senior producer and writer.
Dinello’s imprint is evident across the show’s signature comedic style: the blending of intellectual wit with grounded absurdity, rapid-response political cold opens, and recurring character segments.
Nearly four decades after climbing onto a Second City touring bus, Stephen Colbert and Paul Dinello continue to demonstrate that the strongest comedic partnerships are built on mutual honesty, shared vision, and an enduring friendship.