Daniel O'Brien's Newsletter: Everything So Far
Hello! This is the official substack of me, Daniel O'Brien, six-time Emmy-winning Senior Writer for Last Week Tonight with John Oliver and also more things (see below). This is the latest issue of my substack, a thing you signed up for on purpose.
Every so often I will send an email with:
-Three-to-five book recommendations;
-Updates on whatever I'm working on, if applicable;
-That's really it!
As you might have noticed, I'd been trying to "theme" this newsletter as much as I could, but going forward I think this will just morph into "What I've been reading lately." That's almost definitely less helpful for anyone who was using this newsletter to get meaningful book recommendations; after all, you could argue that books on a theme were always, at the very least, vetted by me (whatever you think my vetting is worth). We were dealing with books that I'd read and also thought would be useful for writers or just plain good for readers. Transitioning to "What I've been reading" makes this newsletter more of a grab-bag.
So why the change? Well, I want to keep the newsletter going and I think focusing just on what I read recently makes that more likely. I read every day and I take notes on every book I read. It's not a heavy lift to just translate those notes for the newsletter. And if I'm being honest, there was more completely unnecessary pressure on the curated version of this newsletter. I was trying to make sure I picked the "right" books for whatever arbitrary theme I'd concocted, and when you focus on picking the right thing you open yourself up to doing the wrong thing, and that's a silly way to accomplish my endeavor which is to create a book club for people.
The revamped version of this newsletter will kick-off next month but in the meantime here is the long-threatened "Everything So Far" post that attempts to explain Who I Am and How I Got Here and Why You Subscribed.
The short version is, I've been writing comedy professionally since 2007, when I was 21 years old. I've been writing for longer but, for my purposes, "professionally" here means "and getting paid for it." The long version is this handy little FAQ.
Wait, Who Are You?
By a wide margin, most of the people who are reading or subscribed to this newsletter are doing so because they saw my work-- videos or a weekly column-- on Cracked.com, a comedy website that for almost a decade was either the first or second-most-viewed comedy website on this planet, planet Earth. We traded the top spot with The Onion, CollegeHumor and FunnyOrDie back-and-forth, and we were easily the least-cool brand in that bunch. It was a fun time in internet content history. It seems quaint now but once upon a time you could make a decent living creating long-form (written!) content for an audience that did insane things like wake up every day and check their favorite websites to be entertained or informed or comfortably distracted.
(These days instead we have social media that we check every day to be enraged or tricked or violently radicalized by. The only websites that exist anymore are about gambling, sites that let you see how much your neighbor’s house costs, pornography and recipes, the only four unbeatable industries in all of human existence).
When I started at Cracked in 2007, the creative team included one full-time employee (Jack O'Brien, no relation) and one part-time employee (me, relation). Jack quickly hired tiktok darling Jason Pargin and for a while it was just the three of us managing the site, buoyed by some truly incredible freelance talent. By 2016, Cracked had evolved into a multimedia content company that was so successful it ended up selling for almost $40 million.
(I'd like to say that again. Just a few people--one of whom was a college senior making $15 an hour to write, edit and design articles-- built a comedy website that in less than 10 years would sell for $40 million. I was that college senior. Wanna hear something crazy? I didn't get a piece of that $40 million sale and-- wanna hear something crazier-- no one I personally know did, either.)
At Cracked, I co-created, co-starred and co-wrote the Webby-Award-Winning series After Hours, which ran for 10 years and accumulated a truly unfathomable amount of views. I also created, starred in and wrote Obsessive Pop Culture Disorder, and created and wrote a web sitcom called Rom.Com-- a cute show about brains and hearts I'm incredibly proud of-- as well as an amount of other shows and one-off sketches that I have, to be completely honest, never actually sat down and counted. We published two books through Cracked, The De-Textbook, for which I was the Head Writer and You Might Be a Zombie and Other Bad News, now a New York Times Bestseller, for which I was a writer/and editor.
My job titles at Cracked went from intern to Assistant Editor to Editor to Head Writer to Head of Columns to Head of Video to Creative Director of Content Development to Laid Off, when the internet content bubble burst and the company that bought Cracked for all that money changed their minds and went “whoops.”
I Wasn’t One of Those Losers Who Went to Cracked. Why Am “I” Here?
If you don't know me from Cracked, there's a chance you know me because of one of my solo books, How To Fight Presidents and Your Presidential Fantasy Dream Team or Quick Question, the weekly podcast I do with my best friend, former coworker and fellow comedy writer Soren Bowie (American Dad!). We do-- no exaggeration-- no promotion for this show, and it gets about 80 thousand listens per month.
There is an outside chance you know me from my Stitcher (Howl?) podcast miniseries Dead Presidents, featuring Ralph Garman, Patrick Stump, Rachel Bloom, Liana Maeby and Hannah Hart.
(That is such a cool list of guests, all of whom we got because I reached out and asked. I truly can't believe how little I was paid to make this show that I don't, at the end of the day, own. Always ask for ownership. If they laugh at you, ask for double what they offer. If they laugh at that, walk away. Another good reason to ask for ownership? It appears this podcast no longer exists!)
Cool? What About the Present, Where “I” Live?
Since 2018, I've been writing for Last Week Tonight with John Oliver on HBO, a late night political comedy show that has won several Emmy awards (Emmys are like Webbys but for TV). It's a great job and has changed my life in more than a few ways, please keep watching it so I can keep writing for it.
Did You Say a Podcast, Too? Oof.
Oof indeed! Quick Question with Soren and Daniel, I don't know if it's been said before, was initially invented to EASILY and LUCRATIVELY CASH IN on the fanbases Soren and I built together in our years making things for Cracked and then it somewhat organically evolved into a show that is about many things but is mostly about-- we hope-- positive, male friendships in the present. I think there are a lot of young, thoughtful boys who end up being drawn to Joe Rogan and Jordan Peterson and Dilbert's Dad for silly ideas about what it means to be a man dressed up by 80s action hero cliches and long-debunked pseudo science. We're a quiet but confident alternative. Without really putting too fine a point on it, we offer ourselves up as imperfect examples of men who are successful and creative without pretending like the world is a jungle where you need to dominate your enemies to achieve goodness.
Sometimes we engage in the kinds of evergreen pop-culture-focused conversations that we routinely did in After Hours or Excessive Pop Culture Discussion, but mostly you're listening to an hour-long weekly phone call between two guys who are doing their best.
That's the story so far! I'm an incredibly lucky comedy writer who has been able to work in some version of this industry somewhat steadily since 2007, and I'd like to keep doing that for a while before ideally getting run out of town for thoughts I have now that will prove to be problematic sometime in the distant future.
After Hours Reunion When?
That’s all the time we have today! Come back next month when our topic will be: Books.