(Foggy Memory Warning: This is my best recollection of something that happened when I was much younger and significantly less resistant to overreactions over perceived injustices. I’m doing my best, but you should probably mentally adjust for the distortions the decade-old memories of a 20-something might produce.)

Theoretically, some people do what they do out of pure, undiluted love of excellence. They get up every day and grind their skills ever finer, like coffee grounds they never intend to brew. They put the output of their genius in a box and keep it as a hidden testimony to the pursuit of art, never to be seen by any but the eyes of providence.

You aren’t really supposed to talk about this, but most people aren’t like that. Some large perhaps-a-majority proportion of people who create are looking for some sort of payout in the form of various forms of legitimacy - if they write for X, they are now the sort of person who can write for X. Some people are looking for money. That doesn’t mean they don’t care about the art/craft parts of the pursuit (they usually still do), but it does mean that there’s an awful lot of people out there looking for places to get their work out in front of people in a way that “pays out”.

In 2010-2017 or thereabouts, the publication doing the best job of pitching themselves to writers as a place to put your goods on display was Cracked.com, a website phoenix rising from the ashes of an old print MAD magazine competitor (one which had met its unceremonious end through an actual literal anthrax attempt - really!). Cracked had invested heavily in the list-based article “listicle” format, and links to their work were waiting around every internet corner, brandishing endless bathroom-break optimized pages promising to tell you five crazy things you didn’t know about a mundane thing X.

At Cracked, a young writer was told, you could access potentially millions of views on a single article. You’d join a list of people from which several successful, known names had sprung. You’d also be paid! Real money! They don’t pay real money to people who aren’t real writers!

And yet it was the worst. Now, fair warning: I’m among some of the most negative-on-Cracked people to have ever got past the lowest tier of their internal writer ecosystem. There’s a lot of people who will tell you a different-sounding story. But for what it’s worth, here’s what I saw there.

The Googler-as-Writer Trap

To write an article at Cracked, a beginner writer had to follow a relatively simple roadmap:

Gain access to the writer’s forums. Depending on the era, there were a few relatively minimal steps to doing this, usually among the types of tasks you’d expect from a place trying to keep spammers out of its workspace.
Pitch an article in a listicle format. Again, listicles are those “10 surprising things you might not have known about Kate Moss” formats you see pop up on Twitter even today. Beginner writers were entirely limited to this format, so this was the first place writers would start to filter themselves out; many wanted to join to do the more individual kind of work the higher-tier columnists did, and this was strictly disallowed.
Find sourced examples. This step generally occurred concurrently with #2; you were expected to bring a few interesting examples of potential list items to the table. These examples would be approved piece-meal by the forum mods/editors, and you were expected to have a minimum of five examples before an article would be sent up the ladder for editorial review.
Get told no by the editors. When articles were sent up the ladder for final review, they would sometimes make it through that review unchanged, but as a general rule they would be sent back for more sourcing. At this point, I want you to note that potential writers have still to write a single word.
Reiterate until the article is approved for writing.
Write a draft of the article.
The article is published with your byline - great kudos are now yours.

The observant might have already noticed this, but take a look at how short that “write the article” section of the roadmap is compared to the Googling-and-sourcing tasks. That is because of a massive negative that Cracked usually advertised as a positive: Every article with sufficient sources and an approved format would be edited/rewritten into a Cracked-voice compliant form by either a hand-selected veteran forum member or (more usually) a paid member of the actual Cracked.com staff.

Superficially, this aspect of the process looked great. A person could come to the table with exactly zero developed writing skills, still get something published, still get paid, and be able to see how a better, more advanced writer would have approached the same topic. To be fair, there is some value there; every now and again a comparable-or-better writer will handle a topic I’ve also done work on, and it’s usually very instructive.

In actual practice, this ended up being bad for most of the people who wrote there. At the time I was working in that space, one of the perpetual top producers of articles was pretty well known to not be able to write at all, and he never improved; whether or not he was capable of it, he had no Cracked-provided motivation to do so. His stuff would get published either way.

The trap here, such as it was, was that Cracked had no shortage of actual, salaried staff capable of creating the half-dozen or so pieces of content they needed every day; if all they needed was word count, they could handle it on their own. so long as those people had a ready, eternal supply of topics to write about.

What they didn’t have (and couldn’t have) was a stable of people with the same amount of talent who could come up with fresh ideas every day and who were willing to devote the massive amount of research time each article required. So they took a page out of the book of their E-How-and-Livestrong-owning Demand Media parent company’s book and outsourced that bit to the masses.

The important bit of the process - the part that got you paid - was the research bit. You could have low-level ESL English skills and still “write” for Cracked, and people did. They got bylines like everyone else, and got paid the same, but were at their foundation a corps of researchers-not-writers.

All of this was fine until it was generally known.

“The Applebees of Writing”

Within the hierarchy of the outsourced writing masses of Cracked, the pecking order looked something like this:

Contributors. These were the first-tier disposables of the process I described above, and at any given time there were thousands of them.
Forum mods. Forum mods were just what they sounded like - people who kept the writer forums clean and churning by doing mechanical moderation tasks. They generally were folks that had a decent enough grasp of what Cracked was looking for in content proposals to do a first-pass filter of the clearly bad stuff. They were not paid for this outside of compensation in the form of a bit of shoulder-rubbing with the higher-ups and a small amount of preferential consideration of their own submissions.
Freelance editors. Freelance editors were a latter-day addition to the ranks of Cracked and were essentially people who had written close-enough first drafts enough time to be recognized as first-pass editors. They got regular freelance work doing this, essentially taking more low-level tasks off the plate of Cracked’s actual salaried staff.1

At some point, it became known that one of the longstanding tier 2 moderators was being promoted to tier 3. This was, as I recall, a very nice person; she was sincere, polite, and worked hard. And this was a big deal for her; she had worked hard, and was now at the highest position one could rise to before being promoted to actual staff (or not being promoted; more on this later).

The way the story circulated, she went to one of her close friends (also a writer) and told her about this so she could share in her joy. The friend said, in as close of a quote as I can remember, something like “Oh, honey, that’s great for you. But isn’t Cracked sort of the Applebees of writing?”2

In the early days of Cracked, before hirers became familiar with how they did business, stories like this (from the link in the introduction) were at least somewhat known, if not common:

Sometime in 2009, as a result of my work at Cracked I landed a job doing freelance writing for a pair of music and movie sites. Later I was hired to run another comedy site, and from there I was offered a job writing for a new site owned by Playboy. So to summarize, less than four years after signing up to write for Cracked, I quit my day job to work full time for Playboy. I know what you're wondering, and the answer is yes, I did get to go to the Playboy Mansion. Only once, though. And I had to pay for the flight myself. But still, if I had never responded to that call for writers back in 2007, I never would have even been invited. And I most certainly wouldn't be where I am right now.
When Playboy sold off their digital business to an international porn conglomerate, I saw it as a good time to explore my options. As luck would have it, Cracked was hiring. After a few telephone chats, I agreed to come on board as a full-time editor (hello again, health insurance!) at Cracked.com in December 2011. Eventually, I left South Dakota, and after stops in New York and San Francisco, I moved to Los Angeles to work from the Cracked offices. You can see the ocean from the room where we have our editorial meetings. Things are a lot better for me now than they were on that brutally cold Thanksgiving Day in South Dakota in 2007.

But note that he’s talking about 2009 - he was an early Cracked contributor, one who got in before Cracked’s system was nearly as codified and stiff. Even after Cracked put the whole process on no-skill-needed rails, they never stopped making promises like this:

Get all the degrees you want, but nothing is going to look better to a prospective writing employer than verifiable proof that your words are capable of entertaining a lot of people.

Non-Cracked writing employers got wise all the same; after a while the only places a Cracked reference worked particularly well were other, lesser listicle producers/clickbait makers. To be fair, this wasn’t an absolute effect - not everyone would have been intimately familiar with Cracked’s researcher-as-writer formula, and “I have written somewhere” was still very much better than nothing.

Did Wokeness Kill Cracked?

There is, as you are probably aware, a media property called Pokémon. You are a little less likely to be aware of this, but it’s the most successful media franchise in existence. Kids love it. Adults love it. It’s a big thing, and it’s been a big thing since Kerry Strugg brought home the Olympic gold in a stunning display of gymnastics bravery unmatched through history or since.

Cracked, for some reason, would not allow people to write about it. During my time there, I saw dozens of workable Pokémon related pitches; the vast majority of them were rejected because “Nobody on staff likes Pokémon, or understands it very well”. Newbies would come in, make the entirely justified assumption that it was an underserved topic that would generate a bunch of traffic, then run up against that wall; without some other kind of leverage, it was an unassailable and clearly counterproductive rule that stayed in place for literal years.

Now, to be very clear: This isn’t a big deal to me, personally. I never pitched a Pokémon article and I’m not bitter about this on an individual sour grapes level. I bring it up to illustrate a single point: Cracked was completely OK with quashing articles they didn’t like much, audience-and-traffic be damned.

This in turn mattered because if there was one thing Cracked hated more than Pokémon, it was anything to the right of a very conventional California-left worldview. This panned out weird in a lot of ways:

If you haven’t figured it out from the rest of the article, the number of people who Cracked ever promoted from the inside was a rounding error on zero. They very much preferred to bring in talent from the outside. There were thousands of contributors, perhaps a dozen mods, and a few freelance editors. In my couple-of-years-there experience, I think something like two people got promoted to staff; the filter was just too powerful and the staff too small to offer more.

But it was still generally known that if you wanted so much as a chance at breathing that rarified air, you needed to be politically in line with staff. This might be a coincidence (anything might)m but the people who did get promoted to staff were vocally left and made sure that showed in their work. The most conservative person on staff was David Wong, and I once saw him uphold a ban on someone from the forums for questioning whether an off-hand mention of Ron Paul was enough to write a celebrity off as garbage.

I don’t think this is particularly surprising in a California-based company of comedians, but it also wasn’t exactly mentioned in the big cattle calls for new writers - roughly half of the people who showed up for those were getting handed type-B fame scratchers cards with “Fuck you, Nazi!” written under the foil. Nothing about this should have been a shock, but there were still almost certainly some people working hard to climb the ladder who never knew it was de-facto banned for non-Clinton voters.
Sourcing articles was really weird, because the average intellectual firepower wielded by a Cracked staffer was born and died in “I read it in the NYT” territory. So, for instance: say you wanted to write an article about things newspapers got wrong, and one of those newspapers was big and left-leaning. You’d immediately run into a pretty hard wall of dealing with a person who had never seriously considered that a respected source could possibly be wrong, even if contradicted by the primary source the article was reporting on.

The flip side of this was that any site that wasn’t a known-left publication was effectively banned for use, at least in the case of articles that covered any sort of politics. Since sources were required, this amounted to a soft, only-sometimes-circumventable ban on disagreeing with the left on anything important.3
It affected content in a pretty big way. As the staff got less and less “young artists trying to make it” and more and more “old jaded artists who feel entitled to do real art that really matters”, they became more and more heavy-handed about what was and wasn’t politically aligned enough to be funny. And fans noticed; posts like this were everywhere.

This sort of general “don’t even try if you aren’t consistent with our views” environment was nowhere as apparent as it was in the unspoken-rule restrictions on Cracked’s “I am a” personal experience articles.

These IAMA articles were created under the heavy influence of Robert Evans, who now makes a living screaming about how Nazis are going to eat the pacific northwest and documenting how great Antifa is, or something; in a left-of-center group of California creatives, he was visibly the farthest left by a fair margin. This post isn’t a great authoritative source, but it reinforces my impression there was a subset of life experiences that were deemed both interesting enough to be readable AND left-friendly enough to satisfy the Staff; anything else got axed.

To this day, if you find a person from Cracked’s staff talking about #3, they will swear up and down that the site never drifted significantly leftward or that the drift, if it did exist, could have ever penalized someone for having a divergent viewpoint. To be fair, this is a pretty subjective subject; it’s hard to pin down solid, provable truths in this kind of conversation.

What was less in question was that something like a third of Cracked’s audience felt constantly alienated by Cracked’s content. The natural question that flows from that is “So is that why Cracked imploded and suddenly dropped off everyone’s radar?”. It’s a reasonable question. Media websites tend to live and die by traffic, and any actions taken to reduce that traffic make sense as possible causes of death to consider during any website’s postmortem.

As much as I’d like to say yes, the answer is probably no. At its height, Cracked had millions and millions of uniques a month; even if they successfully alienated every single conservative, the effect would have been more in the “scaling back staff” realm of things than the “our site suddenly fails forever and ever, becoming a shadow of its former self”.

I don’t personally think that moving Leftward was the cause of their fall - hell, pandering to one’s biggest audience components might have even helped them delay it. But just because something isn’t a cause doesn’t mean it’s not illustrative of the environment that caused the fall, and so I believe it is here.

So what can cause a comedy site to shift farther and farther to the left that also causes it to fail?

(nearly) Everyone got spoiled

Here’s an old story:

A young actor works his whole life honing his craft, hoping against the odds that he is noticed among the masses and allowed to be successful - that he can appear in movies, become rich, and be acknowledged as famous. Against all odds, this happens; he’s joined an elite few and is the envy of millions of aspirants in his craft.
A year later, he does an interview explaining that he’s kind of over the whole actor thing and is ready to direct.

Everyone working at Cracked during the golden age was envied in the way that actor was - every single contributor in that forum wanted to hang out with them, and would have done just about anything to join them at “the top”, such as it was. But being envied doesn’t keep you from getting spoiled, it just convinces you that it’s OK when you do.

I can’t find it now, but there was once a really really bad video that came out, and I was discussing it with a higher-up in the editorial staff. They said (I’m getting this as close as I can) that the video was the result of a bunch of people forgetting they have fans - of being spoiled, and of making stuff purely for themselves. And a lot of senior-staff output went that way; they wrote fewer and fewer articles and made more and more videos that were outside the realm of what their fans wanted to see.

I don’t think that any of this was really a mortal sin; I can’t really look at a group of creatives and tell them they should have stopped pushing for bigger and better things. And it wasn’t like the output was that bad - they still made a bunch of really entertaining stuff. But then the whole world changed, for it was then that Facebook announced the Pivot to Video.

If you don’t know about the Pivot to Video, good - you probably have meaningful relationships. But for those that don’t know and didn’t click the link, it was essentially a period when Facebook announced, unbidden, that the future of the internet was entirely video and that non-video content would eventually do poorly on Facebook. It later proved to be false, but for a site like Cracked (which was heavily reliant on Facebook views, and increasingly dying of revenues lost to ad-blockers) it would have been a compelling threat to take seriously, one that would have justified big, big bets.

Cracked bet nearly everything on video. They geared up hard, spent a ton of money on increased production capacity, bet hard on a few series and were thus mostly ready for the Pivot to Video. And then, you know, it never happened. All the bets failed to pay out, and Cracked almost instantly sold to Scripps, who seemed to have little interest in Cracked beyond using them as a tax write-off in ways I don’t fully understand.

Can I say for sure that a less-spoiled staff4 that Wouldn’t have made huge bets on special effects and focused clever writing rather than special effects and demo-reel-friendly clips would have weathered the storm better? I can’t, but it sure seems like a possibility.

And Yet I Am Thankful

It’s really easy to be bitter about stuff, but I’m actually sort of glad in a lot of ways that Cracked wasn’t a great environment for me. You know who would have been miserable living in LA with a bunch of people who thought they were smart because they read a lot of Newsweek? This guy.

Even more than that, I have to acknowledge that even if they didn’t give me a place where I could write from ever-higher rungs on a clearly defined advancement ladder like they kind of implied I could, they did give me a place to write - I got to talk to a lot of young writers about what we were trying, and I got to have some interactions with people who were (then and now) more successful at what they did than I was/am.

And that’s, you know, that’s sort of how it is. If I was smart, I wouldn’t write at all - it’s a hard world, and one where success doesn’t always follow hard work. For every Cracked that does well for a while, there’s thousands of sites that wither and die. It’s easy to criticize choices they made after the fact and say I would have done things differently, but it’s also possible the fix was in no matter what they did; nobody wins king-of-the-hill forever except Mike Judge.

So I’m (mostly) thankful. I don’t think these people were perfect, and there’s some stuff I wish they didn’t do. But they gave a lot of people a place to write, and if nothing else also gave them a place to realize how hard of a world writing is, and that success there is mainly something you can’t rely on other people to provide.

Subscribe now

Share

1

Later on, almost past my time there, I understand that Cracked opened up a sort of hybrid role between these three categories and being an actual salaried staffer, in which a very veteran and very well-liked contributor could pitch articles that “broke the mold” a bit and ventured more into the “my opinions, my voice” territory staffers mostly monopolized. I should talk about this more (and would like comments on it if anyone has insider insights) but I just don’t have enough knowledge about it, and it wouldn’t have made much difference given my understanding of the timeline of Cracked’s eventual fall.

2

OK, so, holy shit this particular line has stuck with me. Imagine a friend comes to you and is very proud of becoming a chef, and is presenting it as “I’m finally a chef!” and then reveals that they are a chef at Applebees, where you are vaguely aware they have very limited executive freedom to the point where “chef” doesn’t quite seem the right term anymore. Certainly you’d still be nice about it and the right reaction is NOT to make them feel bad about it, but this example makes you feel that conflict in your bones - like if I said I was an architect and built 100 houses last year, and you found out they were dollhouses built from pattern-stamped balsa.

I have for years now been curious as to who this person was; it’s such a great line and such an effective mental image that I’ve just never really stopped thinking about it. I will never know who this (evidently good) writer was. I am haunted.

3

One thing that I wish I had more time to talk about is how much different of an era it was, even just 5-10 years ago. “Woke” was not a term in common use; the usual term for someone performatively doing their best to ban dissenting viewpoints from their space was Social Justice Warrior, which carried a different set of secondary connotations (considered annoying instead of a major censorship threat, more-racial-less-sexual-except-just-Lesbian-and-Gay-issues-and-still-less-even-then, etc.).

But more importantly, counter-left media hadn’t made nearly as much headway showing how often, say, Rolling Stone or NYT played fast and loose with facts. People didn’t question “the media” as much as a unified body of usually lying people, and the left was basically making a lot of hay selectively pointing out the (often real) failures of Fox News, guilt-by-associationing all other right-wing sources, and ignoring all other problems.

This made for some weird situations where, for instance, you could probably use Jon Stewart as a source (because he was trustably left and thus incapable of error, and also would have provided a fun clip) but would have had trouble using Charles Krauthammer.

4

You might say “But who wasn’t spoiled?” and the answer, as near as I can tell, is Dan O’Brien. There were probably others! There were good people there.

Resident Contrarian

Another Semi-Insider Article About…