A Q&A with Jason Gay of The Wall Street Journal on how to write funny, being on TV with Regis and covering sports for the WSJ

Every week we will run a Q&A with a wonderful reporter to talk about what’s right and wrong with journalism, their interests and random other stuff. Some are friends. Some are just people whose work we really respect. Some cover sports. Some don’t. Hopefully all will be interesting.

This week, it’s with Jason Gay, the incredible sports columnist for The Wall Street Journal. Jason is one of the most talented people in all of sports media, and we talk to him about what it’s been like to see the growth of the Journal’s sports section, the genesis of his beloved Thanksgiving football column and how he got so darn funny.

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The questions are in bold. The answers are not.

  1. How did you break into journalism and land at the job you have now?

Hold on to your hats, gang, because I broke into newspapers covering the dangerous, high-stakes world of small-town Little League baseball. That was me, asking tough questions to 12-year-olds who couldn’t hit the cutoff man. But I desperately needed that experience. I needed any experience I could get. I didn’t go to journalism school, I didn’t read the Janet Malcolm book in college—I barely paid attention in college—and I didn’t know a thing about how to write a newspaper story. There are still days I feel that way, guys. I may be fabulously good looking, but I am not very smart.

One thing I learned very quickly covering Little League: After the game, you could always get the players in line at the ice cream truck. Nowadays, I think it’s harder. Today, I think most Little Leaguers prefer talking to the Little League Players Tribune. It’s a shame.

As for my current job, I had an old-timey newspaper background. You guys remember newspapers, don’t you—printed on paper, thrown in the driveway at 5:30 AM, etc? I was a paperboy, then I sold ads at a small paper, then I wrote for the same small paper, then a slightly bigger paper, then a slightly bigger paper than that…I sound like I’m talking about working on a steamboat in the 1920s. Did I mention that I am 399 years old?

2. You entered The Wall Street Journal sports department when it was pretty much a brand new venture. What was it like being part of what was essentially a journalism startup at an enormous institution? How has the section evolved over time?

Embarrassing but: I wasn’t a Journal reader. I knew it was this great and well-respected paper, and it sounded really awesome when I told my father-in-law I was going to work there. But if I had known about all its traditions and influence when I started working there, I think I would have passed out. Ignorance helped (still helps!).

As for the sports section’s evolution, I think internally there’s a sense for what a good Journal sports story is, which I believe is a story that is, at least in small degrees, different than a sports story you would encounter anyplace else. Maybe it’s weird, or wonky, or funny, or counterintuitive, but it doesn’t fit the traditional sports writing formula. I think our readers have come to appreciate that. Or maybe they’re just lost and trying to find the Personal Journal section.

Maybe it comes down to this: Surprise people a little bit every day. I think that’s a good goal. Jeez, I sound like I’m giving a TED talk.

Guys: if I sound at any point in this interview like I am giving “rules of writing,” please hit me over the head with a metal garbage can. Every time I read one of those pretentious “writers on writing” things I want to throw up out a window.

Also: Do I get any money for doing this? Sandwiches?

3. How often do you come across people who are surprised that The Wall Street Journal covers sports? How is the sports section viewed within the paper?

A lot at the beginning. Lot of jokes about “want a stock market tip?” from athletes, etc. I always thought it was funny—it IS weird The Wall Street Journal had a sports section! It’s STILL weird! It’s like Sports Illustrated having a mutual funds columnist! But I think being an unlikely sports destination has worked to our advantage.

As for how the sports section is viewed within the paper: We’re lucky stiffs and we know it. We’ve have benefitted from some really powerful and encouraging advocates, like our boss-of-bosses Gerry Baker and before him, Robert Thomson. We’ve had wise and benevolent editors, too many to mention. We are really lucky to be in a paper surrounded by ludicrously smart and courageous reporting from all over the world. I know this all sounds like an ass-kissy thing to say—SMOOOOOOOCH!!!—but it’s 100 percent true.

I think everyone in sports has benefitted from the paper’s incredible reputation and standards. We didn’t have to start from scratch.

4. One of your hallmarks that sets you apart from other sports columnists is your ability to write funny. How did you hone that skill? How can other writers learn to inject humor into their work?

I have no other life skills, Jared. If this doesn’t work out, I am selling hand puppets at the mall. And also: thank you for thinking I can be funny. There are people who would argue otherwise, some of them living in my own home.

As for the “how to be funny” thing: That’s such a hard question to answer without sounding like a jackass. Let’s try this: Sports are inherently fun and goofy. Serious stuff happens, but ridiculous things happen even more, and the stakes, by and large, are low. I find it really, really easy to see the humor in almost any sports story. After all, sports is mostly people running around in funny pants.

Maybe a better question is: How can anyone take sports super seriously? I find that fascinating, when I see people on TV arguing about college football like it’s the national debt.

5. Perhaps your most beloved piece is your annual Rules for Thanksgiving Football column. How did that come about, and what has made it so successful?

That’s 100 percent Journal readers! I wrote the first one because I was leaving on vacation and lazy and I needed an idea I could write fast. For whatever reason, it caught on with WSJ readers, who not only shared it with friends and family, but sent in their own ideas for rules and even photos and scores. It just took on a life of its own that was completely beyond what I imagined. It’s now a tradition, so of course, I need to completely run it into the ground, if I haven’t already.

6. One of the things I (Mike) enjoy about reading The Wall Street Journal sports section is that it doesn’t take sports too seriously. Why shouldn’t we take sports and sports journalism too seriously?

Mike! Thanks for the question. Sorry you have to spend so much time with Jared.

As for your question, I want to underline something, which is: We might not take the topics terribly seriously, but we do take the reporting seriously. Like every other desk at the Journal, we strive to be responsible, get it right, be dogged and fair. Even if the topic is goofy, accuracy is paramount. I had to look up “paramount” there to make sure I was using it correctly.

What I mean to say is: for every dumb thing I’ve written, there are so many brave and well-reported pieces, from the stuff Matt Futterman has done on global sport to Josh Robinson and Sara Germano’s Olympic coverage to Reed Albergotti and Vanessa O’Connell’s complete unraveling of pro cycling and the Lance Armstrong USPS era. That was hard, serious stuff.

Can I step on a soapbox for a minute? I’ll be brief.

I feel I read all the time from these journalism professors and media gurus about what audiences want and How to Save The Business and blah, blah, blah—half the time this advice winds up contradicting itself in the space of six months. Like it was, “Get on Facebook or die!” and now it’s, “Don’t let Facebook swallow you whole.” I’m utterly committed to trying every new thing, and I’m currently working on some fascinating digital stuff with some really great WSJ people, but what I always find amusing is that when all the data is collected, it becomes clear again and again that what readers want are … interesting stories! They want interesting stories! The mode of delivery may change radically, but I do not believe tastes change radically. Good stories—and news—rule. Period.

Now I really sound like a TED talk. Barf.

7. You recently wrote a book called Little Victories, which besides being hilarious and poignant, is also quite personal, discussing issues such as you and your wife’s difficulties conceiving a child. What made you so comfortable revealing such intimate details of your life to a wide audience? How difficult was it to write personally and intimately about yourself and your family when your day job is to write about others?

I got good advice when I started writing a column, which was: Be yourself, jerkface. That meant not only refusing to take a position that I didn’t believe in, but also letting people in the door a bit. That’s an odd sensation at first—I grew up with editors who, very correctly, advised us to keep ourselves out of stories. It was years before I wrote anything in the first person.

But if you’re going to do that, I think it’s important to be a 360 degree human being. Let people know your failures and flaws. Nobody wants to read 800 words from a braggart or a blowhard. Or at least I don’t. Acknowledge your mistakes and failures. Bonus: Your mistakes and failures are usually hilarious!

Now I sound like I’m giving a bad graduation speech. But what I mean is: If I was going to do a book dispensing real life advice, I would have to offer real life things about myself. So that meant getting into some personal stuff in terms of mistakes and struggles like having a child. It’s been gratifying how many people I’ve heard from who’ve endured similar struggles and could relate in a small way to that. That’s a genuinely moving thing, and I’m grateful for that.

Also: I did not reveal everything in the book, like how I have been married 11 times.

 8. You also spent some time as a full-time panelist on the Fox Sports 1 show “Crowd Goes Wild” with Regis Philbin. There’s so much to ask about that. What was Regis like? What is it like going from preparing to air to being canceled in nine months? And what lessons can we learn about sports television from Fox Sports 1’s still brief existence?

This is like 17 questions! OK, let me try to tackle all of that: Regis is lovely. I know you would prefer it if I had some Krusty the Clown type stories of Regis chain-smoking and getting into bar brawls, but it sadly never happened. He’s pretty much same adorable guy you see on TV, including the brilliant Regis technique of loudly punctuating his points like “Who IS this guy” and speaking in third person (“Give Regis his newspaper!”). It’s the best. He’d come into the dressing room to speak to Trevor Pryce and we always got such a kick out of it. “What are you guys WATCHING? Is this SOCCER? Where are REGIS’S YANKEES?”

I saw him recently and can report he’s still Regis, still lovely, still perfect, still fit as an ox. I will love him forever.

The TV thing was a trip. I used to cover television, years ago, for the New York Observer, and I can say I learned more about the format in 4 weeks on air than I did in years of covering it—you learn a lot about why things are the way they are, what’s hard, what’s easy, what’s dumb, what the people who are great at it do well. I was definitely a stranger in a strange land. But it was fun, the FS1 people were very kind to me, and I still keep in touch with a whole bunch of people from the show. Very much a net positive and that’s a rare thing.

As far as the cancellation, I mean, it’s what happens to pretty much everything on TV. That doesn’t make it easy—and there are a lot more people than just the on-air dingbats who are impacted when a show goes down—but over time you can be philosophical about it. None of the shows we came on the air with are still on the air. Shows that replaced us have been replaced. It’s a turbulent environment. Jared, I am sure you were very sad when the New Beverly Hills 90210 got cancelled. It’s a pass/fail business. Deliver or die.

As to what you can learn….I mean, I know “Crowd Goes Wild” wasn’t exactly “Mad Men,” but I just hope more people who make sports TV can strive to be different. There’s too much sameness out there, too many dudes (or at least 95 percent dudes) sitting around in makeup doling out half-assed commentary over the same 10 clips from last night’s action. It’s redundant and driven by fear of failure and I find it unspeakably hard to watch.

Even worse are the idiotic me talk/you talk conflict shows that are worse than a kick in the ear. You can see right away when a complicated issue like Colin Kaepernick’s protest comes up: Those shows are terribly equipped to handle the conversation in anything resembling a sophisticated or nuanced fashion. It’s like watching two people hit each other over the head with a fish.

I just think: Try something! Do something original! If for no other reason than the Death Bed Reason: Did I just spend decades upon decades cranking out craptastic sports TV?

I admire my old colleague Katie Nolan for this reason. You know how easy it would have been her to slide into a typical TV formula/slot? I am pretty sure she’s been offered everything in the book. But she stuck to her guns, stayed loyal to her crew of people, because she wanted to be different, do her own thing—and she found a lane and an audience for that. That is really hard to do! I think Katie’s always going to do what she wants and not try to fit into a role. Unless it’s a role in a LEGO movie. She’d do that in a second.

9. What would you change, if anything, about how sports is covered? 

I would like all games to begin no later than 5 p.m.and end before 8 p.m. Also: Can college football just be on Saturday? It’s gotten insane. Can basketball have a 60-game season? Can they move all the Olympics to some place reasonable like Fort Lauderdale?

Oh, you’re asking about coverage: I mean, a lot of it is in what I wrote above with the TV stuff. I just think we should just try to avoid sameness. It’d be great if we saw less of the “you say this/I say that” format. Here’s the good news: You don’t have to pay attention to any of it. There’s never been more good stuff out there. Yes, I wish Red Smith and Bud Collins were still here, but there are so many gifted and phenomenal people out there doing really impressive and exciting and groundbreaking things, and it’s never been easier to find them. Every day I feel I read something great by someone I’ve never read before. Even your stuff is halfway decent, Jared!

I also think that because of cord-cutting and the growing digital sports environment, we’re about to enter a really dynamic period. Some of the corporate strangleholds will erode, audiences will be coming from every imaginable direction, conventional wisdoms will be challenged, and there will be real opportunity for smart and motivated and original people. Sadly, I am 399 years old, so I will be dead before this happens.

10. I (Jared) have spent part of virtually every summer of my life vacationing on Martha’s Vineyard. You worked at The Vineyard Gazette. What was the weirdest, craziest, most “are you serious?” thing that happened during your time on the island?

I did a lot of animal escape stories: escaped pig, escaped sheep, escaped llamas. Those were a lot of fun, readers really enjoyed them, and I miss covering them. I mean, let’s be honest: Who wouldn’t want to read about an escaped llama right now?

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