1960–1966: One Hundred and One Dalmatians, The Jungle Book, death of Walt Disney
The commercial failure of Sleeping Beauty (1959) initially discouraged Disney from producing more feature-length animated films, wherein the closure of the animation department was considered. Despite this, Disney assigned Anderson to work on One Hundred and One Dalmatians (1961). While designing the film's visual style, Anderson learned about a television production studio—Hurrell Productions—was using xerography to produce television ads featuring Disney characters. Inspired by the technique, Anderson experimented with a Xerox photocopier to directly transfer the animators' drawings onto transparent cels, thereby eliminating the inking process. Anderson screened an animation test to Disney and the animators; although Disney expressed concern at the graphic style, he gave his approval stating: "Ah, yeah, yeah, you can fool around all you want to." Furthermore, Anderson applied xerography with the background artwork to match the character animation, giving the film a unified visual style.
As early as 1956, Anderson had begun developing story sketches based on the Reynard the Fox legend. In 1960, Anderson and animator Marc Davis decided to adapt the medieval fable Chanticleer and the Fox into an animated film. Both men spent months developing elaborate storyboards and preliminary character artwork. They had presented their pitch before Disney and several studio executives, in which one voice said: "You can't make a personality out of a chicken." Further development was halted when during a meeting, on August 24, Disney remarked that the problem with making a rooster a protagonist was "[you] don't feel like picking a rooster up and petting it."
Released in 1961, One Hundred and One Dalmatians became a critical and commercial success, earning nearly $10 million during its initial domestic release. The animators had been pleased with the film's linear animation quality, but Walt Disney felt it lacked the delicacy and care of his earlier animated films. In a subsequent meeting with the animation staff concerning future films, Disney harshly criticized the Dalmatians art direction and further stated, "Ken's never going to be an art director again." Anderson was hurt by the criticism and further stated Disney did not speak to him for a year.
In 1962, Anderson suffered two strokes in one week, which partially paralyzed the right side of his body for nearly three years. He recovered with help from his wife Polly. As part of his recuperation, Anderson exercised and visited the Descanso Gardens, near his home at La Cañada Flintridge, California, for solace and comfort. Anderson resumed work as an art director on The Sword in the Stone (1963). However, Anderson was dissatisfied with the film's art direction, stating it "was a toothsome thing; it was an original backdrop painting, soft and foggy and a spotlight effect with characters on top of it, but at the same time it couldn't help but be affected by the looks of Dalmatians in most cases."
A year later, The Jungle Book (1967) went into production, in which Anderson provided additional concept art and backgrounds, along with character design ideas. During one story meeting, Disney assigned Anderson to design the villain Shere Khan. Anderson based his character designs on Basil Rathbone, envisioning Khan as "a very menacing, underplayed villain." The next day, Anderson showed his sketches to Disney, which reminded him of George Sanders (and cast him in the role). Animator Milt Kahl refined Anderson's conceptual sketches and watched Jungle Cat (1960) and A Tiger Walks (1964) for reference. Meanwhile, Anderson contributed visual development on the featurette Winnie the Pooh and the Honey Tree (1966).
With The Jungle Book scheduled for 1967, Disney assigned Anderson to determine whether The Aristocats (1970) would be suitable for an animated feature. Following several months, Disney glanced at Anderson's conceptual sketches and approved the project as the studio's next animated film. Before Disney's death in December 1966, Anderson remembered his last meeting:
In fact, I was outdoors of the building and there was Walt. He had shrunk down ... I was so glad to see him. I knew that whatever he appeared to be was because of his illness, and I grabbed him by the hand and said, 'Gee, it's sure good to see you again, Walt. Happy to have you back.' And Walt looked at me. He was kind of quiet and he said, 'It's sure good to be back, Ken.' And then I knew that he was forgiving me for 101 Dalmatians. I don't knew how I knew it, but I did.