Because Tinyletter is mostly for mail, it’s nearly impossible to find old newsletters. So I’m posting all my old newsletters here so they can be searched, indexed, all that. You’re still better off just subscribing.

Richard Pryor died at the age of 65 on December 10, 2005.

December 10, 2016.

One of my biggest regrets is that I entered the working world too quickly. I graduated on a Thursday, and by Monday, Dad and I were in a car driving me to Los Angeles for my first job. I was always going to be a worker, someone who organized his life around productivity, but I didn’t necessarily have to begin so quickly. My wife went to Spain after graduation and had the time of her life. I should have done something like that. I was in way too much of a hurry to become an adult.

My first job was with U: The National College Magazine. If you’re old enough, you will remember this magazine: It was the monthly full color insert inside your college newspaper, distributed all across the country but produced by four recent college students selected for their one-year fellowship program. We applied during our senior years, got the jobs and all lived and worked together in Santa Monica, California for one year. I considered myself a bit of a college newspaper hotshot, and I was pretty excited to get the gig. I had wanted to go to film school at USC — where my high school best friend Tim Grierson, of the Grierson & Leitch business, was going — but we couldn’t afford it and, besides, I wanted to go where Roger Ebert had gone. So moving out there, and hanging out with Tim, and writing about movies, couldn’t have been more exciting. Los Angeles! I remember the first day I was out there, Dad and I immediately went to try to find Nicole Brown Simpson’s house.

My year in Los Angeles was ... well, unpleasant. I was engaged to my college girlfriend when I left for Los Angeles, but when she came out to live with me two months in (with the wedding impending that January), she changed her mind and she called it off. This led to the notorious “Win Ben Stein’s Money” disaster that ultimately led to my “Life As A Loser” column which ultimately lead to The Black Table which ultimately led to Deadspin which ultimately led for me to impersonate a writer long enough to produce this weekly newsletter for you.


I was 22 years old at the time, and I’d just had my heart broken in the most public way imaginable, and thus I was a total disaster area for that year in Los Angeles. I drank way too much, I smoked way too much weed, I generally floated around the city in a daze the whole time. I used to just drive around Los Angeles by myself for hours on end, smoking and listening to, like, the Chemical Brothers or something, feeling more nihilist and self-destructive than I’d ever been, and have ever been since. And this was of course childish, nothing-had-ever-really-gone-too-badly-for-me before self-destructiveness, which is to say, I didn’t do anything that would put me in any actual danger. I just moped for a year, and moped in a way that made me feel more interesting than I actually was. I was just a sad kid for a year. It happens. If it’s the worst thing that happens to you, you’ll be fine. Besides, I eventually got a column out of it. After one year, I moved back to the Midwest, my one stint in St. Louis, and then 18 months later, I was in New York City for an entirely opposite sort of adventure. Los Angeles turned out to be some odd, mopey blip.

So it’s always strange to be back here in Los Angeles, like I am this week, working on pieces for the Leitch Across America series, which returns next week. Everything in Los Angeles is so different than it was when I was here — funny how major American urban centers change a bit over 18 years — but the place still has the same dopey haze, that dipshit sense that in spite of everything it feels like it will still all turn out OK here somehow, that it did in 1998. My time here was confused and young and stupid, but it was also, in its own way, exciting. You felt like you were doing something important when you were in Los Angeles, even if you weren’t. Especially if you weren’t. I still get that sense. Riding down the Sunset Strip, you feel like you’re in the middle of the something thrilling, a little sexy, a little dangerous, even if you’re just an idiot in an Uber trying to find your friends’ house and way too old to be talking to any of those pretty people walking down the street. Los Angeles will always be this unapproachable place to me, where everything went entirely wrong for me but still couldn’t shake me off the place’s trail. It’s like visiting a museum of decades-old miseries that don’t hurt anymore, and are even sort of fun to remember. Back then, I had no idea how this was going to all turn out. After my year there, Los Angeles felt like the end of time. Returning in 2016, now, the place feels eternal. I’ll get this place figured out yet. I never mind coming back to give it another try.

Here is a numerical breakdown of all the things I wrote this week, in order of what I believe to be their quality. (This is an attempt to have an objective look at the value of my work in a way that I suspect will be difficult to sustain.)

1. Ten Thoughts on the Cardinals Signing of Dexter Fowler, Sports On Earth. If you ask me where my Writing Happy Place is, I’d have to say it’s “dissecting St. Louis Cardinals transactions.

2. $400 Million Isn’t a Ridiculous Number for Bryce Harper, Sports On Earth. Pay the man! (Or trade him to the Cardinals.)

3. A Guide to the Possible Oscar Nominees, The New Republic. One great thing about being back in LA: So many movies! I’m seeing Rogue One tonight, for crying out loud.

4. Think of Bud Selig’s HOF as an Honorary Oscar, Sports On Earth. I am a multi-platform content provider who can combine several different entertainment topics.

5. 30 Players, 30 Teams Who Should Be Untouchable, Sports On Earth. The Fowler signing just has me in a baseball mood.

6. How Much Does Fan Hate Matter for Signings?, Sports On Earth. This piece wasn’t terrible, but I didn’t quite get it nailed the way I wanted to.

As I say every week: If you are the sort to subscribe to a weekly newsletter, I would have to think it wouldn’t be too much of a hassle to subscribe to one of the three podcasts I do. Here they are:

Grierson & Leitch, fun show this week, discussing “Jackie,” “Things to Come,” “Double Indemnity” and the awful, awful “Hudson Hawk.” Plus we talked about the middle school play I wrote called “Rough Day.” There’s even a clip!

The Will Leitch Experience, took another week off, but it’s coming back, swear.

Waitin’ Since Last Saturday, we did a live show from Tailgate Georgia, which was a blast.

I’m about to go see “La La Land,” then go to a UCLA-Michigan game, then go see “Rogue One.” This is Los Angeles at its best, I think.

Have a great week, everyone.