A few months ago, my Mag editors asked if I'd write a story about the past decade of fantasy sports. "Simmons turned us down" was how they wooed me. It's okay. I get lots of gigs that way. I'm Johnny Drama, waiting for the scraps Vince turns down.
Anyway, I immediately started to sweat about how I was going to frame such a huge topic. Then it hit me: The best example I can give of how far fantasy has come is that I am here. Just as ESPN pays Jaws to break down X's and O's and Peter Gammons to bring you inside the clubhouse, I am paid by the Worldwide Leader to be its lead fantasy analyst.

It's insane, right? That I basically have the same job as a guy like Da Coach?

Or is it?

According to the Fantasy Sports Trade Association, 19.4 million Americans and Canadians older than 12 play fantasy. Think about that. Better yet, don't think. Just compare. This past January, NBC aired an outdoor NHL game that drew the largest TV audience for regular-season hockey since 1996. The rating was 2.2, or roughly 3.75 million people. Do you get what this means? (Or at least what it means from my skewed perspective?) Fantasy has obviously overtaken hockey as the fourth most popular sport in America. Remind me to act smug the next time I pass Barry Melrose in the hall.

How in the world did this happen? How did fantasy go from a geeky, hard-to-explain hobby practiced by thousands to something that is as common as Mom, pie and congressional hearings? Well, with some help from my friends (and adversaries), let me take you on a journey to get to the bottom of all this.

According to the Tony Award-winning musical Avenue Q, the Internet is for porn. After spending a good deal of time investigating this claim, I'm willing to throw my support behind it. But I can also say the Internet is a huge reason for the fantasy explosion. All the things that once made the game supernerdy and niche—the endless statistical bookkeeping, the manually created standings—were suddenly being neatly produced with the click of a mouse. It was almost too easy.

Now, the one thing the Internet didn't do is wipe out the dork factor, but let's tackle that issue later. In the meantime, I want you to meet Peter Schoenke. Back in 1997, Peter and his crew launched RotoNews.com (now known as Rotowire.com), giving us fantasy owners a wondrous gift: the player news application. You know, here's an update on a guy, and here's the fantasy spin on that news.
This changed everything. The days of feeling like a moron because you started a quarterback who, unbeknownst to you, had frayed his septum? Over. And you have Peter to thank.

Hey, guess who just popped up on my IM screen.

THE TALENTED MR. ROTO Peter, thank you. Now tell me, how did you start RotoNews.com?
SCHOENKE I was a stock trader in Chicago. Before the Internet, there were terminals on the trading floor that you could use to look up information on any stock. I realized what we really needed was an application like that for fantasy baseball so I could find info on the Padres' fourth outfielder without a subscription to an out-of-town paper. When the Internet came along, I bought some software, built a website and enlisted two friends—Jeff Erickson and Herb Ilk—to start it up.
TMR In 1998, '99, I was on RotoNews five, six times a day. Everyone in my league was.
SCHOENKE Our site got tons of traffic right away. People found us out of nowhere. We quit our day jobs about a year later.
TMR Hold on, I've got a call coming in. Perfect. It's Bill Simmons, a guy whose career took off at the same time that the Internet—and fantasy—did. Sports Guy, how's it going? Tell me something: How has the Internet changed the way you play fantasy?
SIMMONS Twenty years ago, my buddy Camp would mail out the scoring for our football league once a week, and we weren't allowed to make any changes. Now I can be in a bar at 12:59 p.m. on a Sunday and bench guys on my cell. Also, I love message boards and e-mails; they offer crueler, more elaborate ways to ridicule your friends than just calling them up. And is there a more underrated moment in life than checking the waiver-wire results?
TMR Wow, you even speak long.
SIMMONS I also think all these fantasy writers have leveled the field. Everyone likes the same guys and has the same sleepers. I don't like that. I would have all fantasy writers killed or at least tortured. Sorry, Matt.
TMR Very nice.

If the five basic questions are what, why, how, where and when-do-we-eat, we're at the why part now. Why has fantasy exploded? I mean, the web, cell phones, e-mail—all that
explains how it took off. But why did it hook so many people? Why did it create a nation of info-starved, refresh-button-pushing junkies?

Back to the Sports Guy.

SIMMONS For a lot of people, it's the way they keep in touch with their buddies from high school or college. It's why the drafts are actually more fun than humans should be allowed. Also, in the '90s, a lot of high school and college kids were playing fantasy—and getting ridiculed by everyone who was older. Now those kids are adults and make up most of the market, so no one is doing any ridiculing anymore. Really, the only people who should be ridiculed are people who write fantasy columns. Again, sorry.

TMR That's quite enough. I don't need you. I know other funny people who play fantasy. Like Jeff Garlin of Curb Your Enthusiasm. In fact, I'm going to give him a call right now and ask him to explain the addiction.
GARLIN When most people get married, they need an escape. I'm 45, and I find it incredibly relaxing. It's my Calgon. I don't drink, I don't do drugs, I don't gamble. Other than spending time with my wife and kids, this is what I do. I'm in one league with my best friend and a bunch of our friends. I'm in another with a bunch of actors and comedians. I'm the commish of both. I thought that scene in Knocked Up in which Paul Rudd gets caught at a fantasy draft was hilarious. I was like, Hey, that guy's in my league. It's just a great way to keep in touch with friends.

And so we return, as promised, to the dork factor. Because it's one thing when it's just you and me playing fantasy. But when it's movie stars? Or better yet, the players themselves? All of a sudden, over the past few years, fantasy has become, well, sort of cool. I mean, Indians closer Joe Borowski is in 10 leagues. Broncos receiver Brandon Marshall told me he knew he was going to have a big year when Jay Cutler picked him way too early. Then there's Chris Cooley. The tight end for my favorite team, the Skins, plays in four leagues. He's one of us. Just ask him. Or better yet, I'll ask him.

TMR How long have you been playing fantasy?
COOLEY Since my junior year in high school, 1998. Three or four of my buddies were in a computer class, and we were all huge into football. Thing was, I always drafted Jeff Garcia.
TMR Oh yeah?
COOLEY Yeah, and you know, I was on the Pro Bowl team with him this season. And I kept wanting to tell him, "You're like my all-time fantasy player, man." But I couldn't bring myself to do it.
TMR I'm thinking that, as someone who plays football for real, you must be really good at fantasy.
COOLEY Well, I lost to my fiancée in the semis this year. Three years ago I was also in the semis, and the guy I was up against had me as his tight end. I ended up scoring three touchdowns against Dallas. Basically, I knocked myself out of the playoffs.

This leads me to a question: Where were you when Brian Westbrook intentionally went down at the 1-yard line this past season? Or when Kerry Wood struck out 20 as a rookie in 1998? I'm sure you have your own most memorable moment. Here's mine: Back in 2002, I was in a 12-team NL-only experts league, and at the All-Star break, I was 13 points … out of 11th! So I threw a Hail Mary, trading every single player I had for random underperformers, hurt guys, you name it. And every one of my new guys had huge second halves. On the next to last day, I was actually in first place, half a point ahead of a guy who is now my colleague, Brendan Roberts. Then, in a meaningless season finale, Luis Castillo stole three bags, I dropped a point in steals, and Brendan won by half a point. Crushed me.

Can anyone top that? Sports Guy?

SIMMONS In a basketball league in 1998, I lost by something like six points scored because David Robinson missed three games at the tail end of the season with a concussion. How do you miss three games with a concussion? I don't think I've ever hated anyone more. All he had to do was play one more game and get six points, and I would have won. David Robinson, I will never forgive you.

Rough. But that's not nearly the worst story I've heard. I know this guy, Tim Lilly, who had the inside track in his baseball league back in 1998. His team was rolling when … well, I'll let Tim tell it.

LILLY Our closer, Armando Benítez, came in to finish the game, but he gave up a three-run home run to Bernie Williams to blow the save. With the next pitch, he drilled our first baseman, Tino Martínez, causing a brawl. So he was suspended for eight games, and Tino wasn't the same for the rest of the season. We finished second.

That's rough. And what I love about it is that only guys who play fantasy can relate. They'd also understand this: I'm in some small restaurant in rural Italy, on a romantic vacation with my wife, when I see on a CNN International ticker that Carlos Beltrán has been traded to the NL. The biggest in-season, non-trade-deadline, interleague trade of the past decade and I'm in Italy, nowhere near a computer. Finally, I find a pay phone, call my brother and make him log on as me to put in a bid.

And I wonder why I'm no longer married. But hey, that's fantasy life for you. Nobody understands it better than the Sports Guy. So despite all the unsavory things he has said about me, I'm gonna let him bring it home. (I'm big like that.)

SIMMONS I think my fantasy highlight of all time was the night I tried to swing a trade for Ichiro as I was walking the carpet at the 2004 ESPYs. It was one of the five most ridiculous moments of my life.

Exactly. And if you've never played fantasy, you're shaking your head, thinking, Bill, it couldn't wait? Are you insane? But to those of us who do play, we get it. We've been there.

And we wouldn't have it any other way.