Zen Diaries is as personal/self-reflective as any Apatow film, and he uses his history/reflections with Shandling to produce a sweet, affecting portrayal of this idiosyncratic personality.
While it’s Apatow’s longest film at 259 minutes, it’s surprisingly investing and rewarding, despite its intense focus on a deeply depressed, distressed individual.
Poring through decades of diaries, we gain profound reflection, introspection, and nuance into Shandling’s legacy, personality, and sense of self-worth.
Apatow’s familiarity with the interviewees, likewise, allows them to open up freely, giving us a genuine warts-and-all examination of Shandling’s tough-to-read internal dialogue.