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. 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.
Poring through decades of diaries, we gain profound reflection, introspection, and nuance into Shandling’s legacy, personality, and sense of self-worth. The results are vulnerably emotional but not too sentimental or assumptive. 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. Its beating heart empowers— rather than detracts from —its emotional searching. Shandling influenced nearly every self-referential modern-comedy but rarely found peace. Thankfully, Apatow provides a lovely, thoughtful, soulful tribute.