Jim Carrey personally created the "Oops" puppet. He said it personifies giving children permission to make mistakes.
When creator Dave Holstein wrote the pilot, he envisioned Jim Carrey] as the only option for the lead character. His drive was such that when he heard Carrey was producing a show for Showtime, I'm Dying Up Here (2017), he managed to get a job as a writer on it so he could pitch Kidding to Carrey.
Michel Gondry was announced to direct the whole first season of the show, but actually ended up directing 6 out of the 10 episodes.
Michel Gondry and Jim Carrey previously worked together on their Oscar-winning film Eternal Sunshine of the Spotless Mind (2004).
On September 14, 2017, it was announced that Showtime had given the production a straight-to-series order for a first season consisting of ten episodes.