Watterson ended the strip on December 31, 1995, and since then remained away from the public scene.
The origin of Dear Mr. Watterson came from Schroeder wanting to understand the cultural impact of Bill Watterson’s decade-long comic strip, so he began as a series of fan interviews in December 2007.
Dear Mr. Watterson launched its first Kickstarter campaign on December 15, 2009 ending March 15, 2010. The Kickstarter raised more than 200% of the goal of $12,000. Since then they have gone on to interview Berkeley Breathed, Lee Salem, Stephan Pastis, Jef Mallett, Dave Kellett, Charles Solomon, Seth Green, Keith Knight, Jenny Robb, Tony Cochran, Andrew Farago (Cartoon Art Museum), Joe Wos (Toonseum), Jean Schulz, Jan Eliot, Bill Amend, and more. And in addition also launched a second Kickstarter campaign in order to fund the finishing of the project. The campaign was successfully funded July 14, 2012.
On November 21, 2012, Schroeder reported to the Kickstarter backers that they had completed the Martini Shot, which is the last take you shoot while in production on a film. In late December 2012, the crew shipped nearly 200 posters as a show of appreciation to backers of their Kickstarter all over the world. Since then they have been updating their Kickstarter with notifications on their submissions of the film to film festivals all over the US, and on March 1, 2013 they announced that Dear Mr. Watterson had been accepted into the 37th Annual Cleveland International Film Festival.
Dear Mr. Watterson had its premiere at the Cleveland International Film Festival on April 9, 2013. The film had a limited release and a video on demand release on November 15, 2013.
At the October 6th 2013 Buffalo International Film Festival screening of the film, children's author, Buffalo native and Calvin and Hobbes fan, Keith White Jr. was in attendance as a special guest. He signed books before the theater doors opened and stayed to watch the film and greet the crowd before the screening began.
The film began with Schroeder interviewing fans of the strip to better understand the cultural impact it had. The strip adhered to topics like morality and animal activism, combined with an imagination and vantage point of a young child, hyper-aware of stereotypes and subjective cultural perspectives. Watterson reported in an interview that he has no regrets of ending the strip when he did, and that he could have gone on repeating himself for another 10–20 years and the fans who were grieving over the strip's end would be wishing it dead for its tediousness.
In an interview with NPR′s Weekend Edition, Schroeder explained that Watterson′s final cartoon exemplified the strip′s enduring appeal. Said Schroeder, describing the panel: “It′s a fresh layer of snow and Calvin and Hobbes are out with the toboggan, and Calvin looks to Hobbes and says, ‘It’s a magical world, old buddy ... let′s go exploring.’ And those last words are just, I think, a challenge to all of us to make sure that we have that curiosity. And words, I think words to live by.”