The focus on spoofing reality TV and having the various sketches begin to cross over was encouraged by head writer John Levenstein, who was a veteran of scripted half-hour television brought on board by Kroll. The two had worked together on HBO's animated sitcom The Life and Times of Tim, but Levenstein's biggest credit was his years on Fox's Arrested Development, particularly its first season, where he helped run the writer's room. Given that show's manic devotion to complicated plot arcs that lasted a season or more, a sketch show was an odd choice for Levenstein. So, during the first season, he began to explore the limits of the form.

"I started pushing more for expanded sketches, the three-parters, and because Nick is such a good actor, in those three-parters I started to give them very emotional elements," Levenstein told me. "In season one, they tended to be within an episode. Armond did begin to travel, from episode to episode, he probably was the first one we started to follow in an ongoing story that evolved. But in season one, the focus was more on stories within episodes, and season two is where we started to stretch more."

A crossover between C-Czar and PubLizIty called "Ice Dating" helped break the traditional sketch mold in the first season, and the experimentation continued from there. "Even though they sort of came out of the same world, they were completely disconnected," Kroll said. "That was the first experiment, and I think we really liked what that meant." The second season of Kroll Show is where it really hits its stride, and sees C-Czar and Liz wrestling with an unplanned pregnancy, Armond on trial for murder, Bobby roped into life as a gigolo, and a deep dive behind the scenes of Degrassi parody Wheels, Ontario, set at a Canadian school where almost every character is in a wheelchair.

"In season two, I had some big linchpins that I wanted to do," Levenstein said. He quickly appreciated the manic intensity of the sketch format, which let him make narrative jumps that wouldn't be allowed in a traditional sitcom. "What can make me crazy in traditional television is all the story points that get fed to the audience that the audience doesn't really have to know. We don't have any of the downside of having to lay pipe for sheer exposition," he said. "We have the freedom to do storytelling without responsibility. As long as the puzzle you're putting together makes some sort of intuitive sense. It doesn't have to make logical sense, cause no one was asking us to do that in the first place."

Kroll, Levenstein, and the writer's room would help break the big narrative arcs and map out the jokes for every sketch, and the actors would improvise more material on set that was then refined and presented for usable takes. Krisel and the editors Bill Benz and Dan Longino (who became the show's directors in season three) would take great care in every sound effect and cut in post-production, since so much of Kroll Show's success stems from its uncanny visual resemblance to the shows it's spoofing.