Dylan O’Sullivan on Flat Characters, TikTok & Bad Art

In this episode of Just Press Record, Matt Zeigler sits down with writer and editor Dylan O’Sullivan (Essayful, Infinite Loops) for a conversation about flat vs round characters, TikTok’s effect on attention, and how to develop real taste in art.

Sparked by a clip from Michael Perry and Aaron Gwyn about “Bob the one-eyed beagle,” they use the idea of a fascinating flat character as a way into comedy, identity, and why some people are interesting precisely because they never change.

Along the way, they dig into defamiliarization, the atrophying pull of short-form video, why some books sharpen your mind while others are pure slop, and how taste is built through reps instead of passive consumption.

They also wrestle with the “ship of Theseus” question of identity, the value of being a little bit “flat” in other people’s stories, and what it means to hold onto a core self while your work and life evolve.

In this conversation, they get into:

Bob the one-eyed beagle and why some “flat” characters are endlessly fascinating
Flat vs round characters in fiction, comedy, and shows like Fawlty Towers and Breaking Bad
Defamiliarization: making the grocery store, a stone, or your street feel strange and vivid again
TikTok, Instagram Reels, and how constant novelty can atrophy imagination and attention
Good art vs bad art: why not all reading is automatically “good for you”
Taste as reps: consuming lots of books, music, and comedy to train intuition and judgment
The ship of Theseus, identity, and the small kernel of self that doesn’t change
Lying to yourself, media shame, and moving from atrophy to growth in what you consume

Timestamps:

00:00 Intro and setup of the episode
04:54 Dylan O’Sullivan on writing and stepping away from short-form content
09:19 Why some characters are interesting because they never change
13:00 Comedy, tragedy, and the appeal of predictable personalities
16:00 Defamiliarization and seeing the world with fresh eyes
20:19 Reading vs. short-form content and the structure of attention
24:54 Passive consumption vs. meaningful engagement with art
28:27 What makes simple stories and humor powerful
32:00 Good art, emotional response, and developing taste
35:00 The role of repetition and experience in shaping taste
38:47 Intuition, self-awareness, and the dangers of passive consumption
41:45 Identity, storytelling, and being “flat” or “round” in different contexts

If you want, I can tighten this further for CTR (slightly sharper opening hook + more algorithm-heavy phrasing in the first two sentences).