Stephen Colbert’s new book, ‘Midnight Confessions,’ features Fairfield illustrator’s artwork

Fairfield, Conn.-based illustrator Sean Kelly designed and created images for Stephen Colbert’s new book, “Midnight Confessions,” including this drawing.

Spread before Sean Kelly are dozens of sketches and drawings, 3-by-5 index cards, envelopes doubling as sketchpads and a red binder filled with the musings of one of late night’s popular hosts.

It was the raw material from which Kelly created the final product that now sits in his hands.

“I was very grateful to be part of the project,” says Kelly, of Stephen Colbert’s latest book, “Midnight Confessions.” Based on the popular segment from “The Late Show” on CBS, during which Colbert reveals various and sundry secrets to his audience members (who ultimately are urged to forgive him), the book is 208 pages of such misdeeds. As with the show, the pithy, odd and hilarious admissions are created by Colbert and his writers.

Sean Kelly

“It is a brilliant motif,” says Kelly, on a recent afternoon at his studio in Fairfield. “You think he is doing good by acknowledging his sins, but they are actually worse than what you think they are going to be.”

“This is the first book where I got to design the entire package,” says Kelly, whose work has appeared in the New York Times Metropolitan Diary, “Businessweek,” “Fortune,” “The Wall Street Journal” and other publications. He also creates illustrations for publications, ad agencies and corporate clients.

Kelly attributes his good fortune to Jonathan Karp, the president and publisher of Simon & Schuster (the publisher of the book), who reached out to Kelly. After sending along some samples, Kelly made the cut and worked intensively for a month determining the fonts, layout and art that would enhance what Colbert’s team had created. Kelly also is grateful to Colbert and his writing staff for their support and creative freedom they afforded him.

“That was the challenge, to translate something that was very personal and strictly about him to more of a universal guilt, so readers could relate,” says Kelly, who also endeavored to create visual gags that would not steal the thunder of the written gag.

For inspiration, Kelly went back to another popular TV segment, “Deep Thoughts” by Jack Handey, which appeared on “Saturday Night Live.” In those a fairly nondescript, serene view of nature is the background for irreverent and absurd observations. It was the dichotomy of those natural views with the rather fresh humor that gave that segment visual power. For Kelly, the challenge was finding visual cues that mirrored the self-deprecating voice of Colbert, and, at times, added a bit of Kelly’s sense of humor to the scene. One, in particular, is Colbert’s somber revelation about a rollercoaster: “I think riding a rollercoaster is the most fun thing in the world. Then again, I’ve never tried crack.”

Kelly’s contribution? A placard that reads “You Must Be This High to Ride.”

“I did this whole map of the book … so there would be this rhythm to it,” he says. Not every “confession” gets an image, and the fonts change throughout. Kelly readily admits that he already had a great head start, given the material was created by some of the top comedic talent in the business.

Kelly will be giving a free talk at the Pequot Library in the Southport section of Fairfield about his work on this book, as well as his approach as an illustrator. The event runs 5 p.m. to 6:30 p.m., Saturday, Nov. 11. There will be books available for purchase. Proceeds benefit the library, for which Kelly serves as a member of its Board of Trustees.

Christina Hennessy