Let’s Remember the Ill-Fated Bill Simmons Cartoon

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In a time when athletic competition has reached a standstill, we seek out sport wherever it might be found. And one of the most beloved sports in the short-yet-fruitful history of the blogosphere has long been taking shots at Bill Simmons.

The premise is admittedly tired, but offering up a take this scorching in the sports-less vacuum is a lay-up.

This fireball of a podcast plug aside, the following serves less as criticism of Simmons than it does to reminisce on just how weird 2000s ESPN was. The Open Man broached this subject before through the lens of the abominable Who’s Now. Around this same time, the Worldwide Leader sought to leverage the exploding popularity of Bill Simmons’ Page 2 column.

Before delving into some of these attempts, some context: It’s safe to assume most anyone who has spent any considerable time in the online sports ecosystem feels like Simmons has been around forever. That makes sense — he’s the first columnist to gain popularity exclusively through web publishing, was in a position of prominence on the ESPN.com masthead almost immediately, and has stayed at the forefront of the landscape for two decades.

Simmons transitioned adeptly to podcasting before the medium really blew up, and his stints as a kingmaker for Grantland and The Ringer have produced plenty of worthwhile content from other writers. The Ringer’s an outlet to which I myself have pitched feature topics.

Despite his ubiquity over the past decade, though, Simmons was still a relative sports media newcomer and ESPN brass seemed intent on figuring out more for him to do.

Page 2, which ostensibly began as a vertical for in-depth commentary and off-beat features (and was rendered superfluous by Grantland), toyed with its own sub-section called “Sports Guy’s World.” Simmons worked color commentary on a handful of mid-major college basketball games in 2007, a few months prior to filming comedy bits for the final segment of the first few installments of E:60. These segments could be best described as the lovechild of Rick Reilly’s Back Page column and Andy Rooney’s commentaries that capped 60 Minutes.

Perhaps less remembered — in part because the platform on which it existed is itself a forgotten relic of the ESPN graveyard —is the Sports Guy cartoon from ESPN360 and ESPN Motion.

ESPN360 lives today under the name ESPN3 (which I wouldn’t be surprised fade in its own right with the advent of Plus, but that’s neither here nor there). Before becoming a place for lower profile events, ESPN360 launched as a hub for original content.

Now, what original content aired on ESPN360, I have no clue. I can’t recall ever using it, nor did I know any consumers despite residing squarely in the target demographic. ESPN360 was the desktop counterpart to ESPN Mobile in that regard, as I never knew an ESPN mobile subscriber. I have, however, read reviews that criticized both for clunky technology. 360 ran through software called Motion that I never successfully installed on my computer.

It wasn’t until well after ESPN360 transitioned away from original content that I discovered the aforementioned cartoon via YouTube. Some intrepid soul cataloged the entire series, with short episodes loosely based on the life of Bill Simmons, as depicted in asides from his columns.

The animation came from the team behind the Nickelodeon series KaBlam!, which my fellow millennials might remember as a family-friendly forerunner to Robot Chicken.

The series is REALLY bad and unfunny, but every episode is roughly a minute long. So please, don’t be a coward: Join me in this journey down a forgotten crossroads of sports and pop culture.