Daniel O'Brien's Newsletter: February '23!

Hello!  This is the official substack of me, Daniel O'Brien, four-time Emmy-winning Senior Writer for Last Week Tonight with John Oliver, author of How to Fight Presidents and its adaptation Your Presidential Fantasy Dream Team, Head Writer for the Cracked De-textbook and editor and contributing author for You Might Be a Zombie and Other Bad News (a New York Times Bestseller), co-host of the popular nothing podcast Quick Question with Soren and Daniel and sole host of the less popular podcast Dead Presidents. I co-created, co-wrote and co-starred in Cracked After Hours, which is easily the most popular thing I've ever done, but that's in the past. This is the first issue(?) of my substack, a thing you signed up for on purpose. 

Once a month I will send an email with: 

-Three-to-five book recommendations;

-Updates on whatever I'm working on, if applicable;

-That's really it! 

It's not my intention to turn this into a blog. I'm trying to hold myself accountable to my goal of reading more books and I'm trying to continue alerting interested parties about my professional endeavors on the off chance that Twitter explodes/implodes/pivots to video. This substack accomplishes both of those things.

One day I might write an "Everything So Far" piece (like my old coworker) that provides an official record of how I went from obscurity all the way to obscurity, but I'm not interested in doing that right now. I want to talk about books, so once a month I'll tell you all what I'm reading and what I think about it. Sometimes it'll truly be what I'm reading at the moment, sometimes it'll be themed. If I have something to promote, I'll do that. But first, books:

Four Books About Writing

A Swim in a Pond in the Rain (George Saunders): George Saunders is a monster, it's insane he's willing to give us what is basically a college-level masterclass in storytelling for the low low price of a book. (He also has his own writing substack which is obviously another incredible gift.) He is a clearly disciplined master who knows that writing happens when you sit down with a pen, pencil or computer and actually DO something, but he also knows to create space for "the Muse" or "the whatever--" the hard-to-define thing none of us writers are in control of. A writer who marries the technical, nuts-and-bolts of writing with the impossible magic of writing is exactly in my sweet spot. He talks about writing with humbleness and confidence simultaneously, and I'm in awe of both.  Reading this book improved my writing and thinking. It's a book that pretends to be a tour through several Russian short stories (and it succeeds!) but doubles as a book about being alive, broadly speaking.

Bird by Bird (Anne Lamott): Confession. I don't like a lot of writing guides. I tend to reject advice on principle. I have a contrarian nature and my hackles go up whenever I feel like someone is trying to tell me "This is the way to do [X]," especially writing. I never connected with any book that presumed to tell anyone how to write. Until, that is, this one. Bird by Bird was assigned to me in some horrible writing course in college and it was the first book about writing that my stupid brain connected with. I know I just said the thing about magic up there, but in general I gravitate towards treating writing like a Job job, a thing you do every day to generate results. Lamont talks about the writing brain like a muscle that needs to be exercised consistently to get stronger, to get better, to produce the kind of work you want it to produce. I never dug into the science to determine whether or not that made any sense and I never care to, because the idea of it made sense to me and it's been built into my writing DNA ever since. Work deliberately and consistently and with intention, that's the takeaway.

On Writing (Stephen King): There's not a lot to say here, Stephen King is one of the best writers in my lifetime and he wrote a book about writing called On Writing. If you've ever wanted to write and you haven't read this book, I would consider you a deeply unserious person and I wouldn't really listen to you with my whole ear when you talked. You get half ear.

Naked Playwriting (William Missouri Downs and Robin Russin): I can't name a book about writing that I've re-read more than this one. Even if you don't necessarily want to write plays (a thing I quietly want to do very much), this book will be helpful for you. Insofar as I have an origin story as a writer (gross), an essential part of that story was the three years in high school I spent reading a different play every day (I was not invited to many parties in high school). My high school had a deep library of plays and I took advantage of it instead of doing whatever it was I was supposed to be doing. (A rebel with a cause! Plays!) Naked Playwriting helped explain to me why I liked what I liked and how I could apply (steal) it for my own writing. Also I think my early obsession with plays goes a long way towards explaining why I'm pretty good at writing dialogue and pretty awful at writing, like, what houses look like or what it feels like to move around.

And that's it! That's the first episode(?) of this thing. Read books, run, volunteer at your local food pantry and call your parents. Bye.

*NOTE: I think if you click on any of those links and buy a book, I get a commission, but I don't totally know for sure because I haven't looked into it too deeply.