Saying Goodbye To Jack O'Brien, Cracked's Cool Dad
Legendary Cracked Editor-in-Chief Jack O'Brien has, after 11 years, left the company for browner pastures. He was not fired or forced out under the cloud of scandal, he didn't get fed up with our bullshit and storm out -- this process has been all tears and going-away gifts. He got a great offer several weeks ago to do something really cool and just decided the time was right.
So, some of us who worked with him have collaborated to prepare a kind of eulogy because he is, of course, now dead to us.
I submitted two articles to Cracked ten years ago. One of them -- a comedic, non-fiction, observation-based essay about Die Hard -- was accepted with a few notes. The other -- a sketch titled "The William H. Macy Institute for Hard-Fucking" -- was neither accepted nor discussed. In part because it was awful, and in part because we didn't (at the time) do sketches or have a video component at all.
I was quickly introduced to the founder of the site, Jack, or more accurately, one of the many nicknames he preferred to go by (The Jacker, Jacklemore and WOO-is, A-Jack of the Clones, Jack of Lamb, etc). New Jack City reached out to me in an email and said, "Hi Dan O'Brien, my name's Jack O'Brien (no relation) and I'm the Editor-in-Chief of Cracked. You showed a real understanding for the voice of the site, which isn't easy, so I want to find more work for you and also just sort of get your story and see what you're interested in with comedy and writing."
There's more stuff in the email, but I'm focusing on the part that I quoted.
Once every few days I think about the "(no relation)" joke and how to me it's a pretty perfect joke. The depth of that joke -- a stranger introducing himself to a stranger with the same last name assuring him that they're not related in a common shorthand -- has always stuck out to me. I am prepared to share an essay's worth of words to explain why I love the efficiency of that joke so much if anyone wants it, but I won't bog this down with that. I only bring it up to say the first nine words The Jacks of Life ever wrote to me contained one of my favorite jokes of all time. And now that that's been stressed, I'd like to go further and say that the joke, with all of its importance to me, is still probably the least important aspect of my introduction to Jack. (Or, again, a nickname he preferred to go by, including but not limited to "Humpin' Jack Splash," which is what he insisted I call him when I officiated his wedding.)
I was a 21-year-old little baby boy kid when I'd first submitted two articles to Cracked, and one was decent and the other was complete dogshit that displayed a fundamental misunderstanding of what Cracked was doing at the time. (Again, we literally did not have an original video component to the site. Why would I write a sketch that REQUIRED William H. Macy as a performer in it, by design?) Objectively half of what I'd done was unusable garbage.
Good Ole' Oyster Jackers has a unique ability to find what is good about a thing, anything, and zero in on it. Even if a thing is literally 50 percent awful, Cactus Jack can find the good parts and shine a light on them because he is attentive and patient and thoughtful. Anyone who has ever been on an editorial call or in a brainstorm room knows how easy it is to discard a half-baked idea and move on to the next thing; the comedian's resting state is "That didn't work, let's keep trying." Knick-Jack Paddy-Jack Give a Jack a Bone stands out for being the one to say, "Wait, let's find the best part about this and celebrate it." He brought that spirit to every single editorial meeting and pitch he ever came across. Some of those meetings were three hours long and the rest of the people on the call were just looking for reasons to turn down a pitch, but he was the one willing to find the good and save it.
His willingness to always find the good in everything is probably why he insisted that we sometimes call him "Jacked," a pun that DOESN'T reference our website but instead is a play on the name of the short-lived sitcom Stacked, the premise of which was "What if Pamela Anderson owned a bookstore?" Jack often said that we could learn a lot from Stacked because even though it was mostly garbage, there was at least ONE good idea buried within it. ("A woman, who could READ!?" he liked to muse before breaking into hysterical laughter. The man contained layers.)
Thursday Night Jackdown and I have never sat down and had a discussion where we formalized or even addressed his status as my capital-M Mentor, but that's how I've always felt and how I've always internalized our interactions. In ten years I've been a lowly intern, the Creative Director for our Video Department with a number of employees who fear me, and everything in between. And throughout that time I've always only had one boss, and it's been Jack.
(Obviously also known as Jackquille O'Neal, Jackquille Whoa-Neal, Shaquille O'Brien, Shaquille O'Jack , Jackquille O'Feel , Jackfeel O'Neal , Snatchfeel O'Feel , Jackquille O'Squeal and Jack-Kills Fo'Real.)
Anyway, he's been my mentor, whether he likes it or not. When I was a piece-of-shit intern with terrible ideas, he gave me a lot of safe room to fail while I learned, and encouragement and guidance when I was doing something right. And when I became a manager here I thought of everything I'd observed from him and applied it to my employees. Every good decision I've ever made as a manager in terms of finding good people, supporting and rewarding them, has been a result of me thinking about a situation and asking myself "What Would Jack Do" if placed in a similar situation. I would eventually shorten this mantra to "WWJD," and that's why today you see bracelets featuring that acronym.
Jack O'Brien, or rather Sic-Jac O'Flyin' (as he demanded to be introduced as when he officiated my wedding, to which he was not invited) taught me everything I know about comedy, leadership, perseverance, and -- for a lot of reasons that don't belong in a public article designed to roast/embarrass him -- compassion, kindness, empathy, and patience. He started this in 2006. I joined in 2007 and there was a time for about two weeks where we were literally the only two creative employees working for this website, and I am thoroughly, fantastically uninterested in continuing this website without him and his guidance. But, of course, I will, because he trusts me to do it (and because I'm paid quite well). But, mostly, it's the trust thing. Jack took a 21-year-old idiot dreamer who sometimes knew how to make people laugh and gave him the career of a lifetime. My only goal now is to do that for as many people as I possibly can.
Also? I know most of you probably know Jack as the stalwart Editor-in-Chief or the no-nonsense host of our podcast or the guy who ... really wants you to know just how much about hip hop he knows, but back in October in '06 he wrote an article called "Yer Gramma Was Built Like a Brick Shit-House in Her Day." It's an essay about a big-dick-having old man eulogizing his silent and ferocious late wife. Here it is.
The first time I told Jack of Faith Disturbing that this was my favorite article, I didn't even realize it was written by him. (Bylines and formatting were screwed up at the time. Still are, TBH.) For all of the people who are choosing to remember Jack-a-mole as the noble and always curious host of our podcast and face of our site, please consider an article he wrote in the voice of an old man celebrating an aggressive and violent grandmother to a child, for absolutely no reason other than he thought it was funny.
"What the rumor mills didn't know was I had an inner fortitude born of faith in the Lord, and an erection you couldn't bend with two hands. And that's not a challenge, that's a fact, mister!"
-Jack O'Brien, in an article titled "Yer Gramma Was Built Like a Brick Shit-House in Her Day" which would go on to be his legacy.
Truer words were never spoken, Jack. Or, as you preferred to be called, Jacktrick Swayze, Jack-Dick Swayze, Jack-Dick Crazy, "Sexy Ghost," The White Jesus, Manaconda, Jack of All Trades, Jack of Even More Trades, Jack O'Caine, Andrew Jacks-FUN and many, many others.
Until the day I die, I'll never wrap my head around all of the things Jack has accomplished in the last ten years. Casual readers know Jack from some amazing articles, a killer podcast, the Spit Take, two books, as the co-creator of After Hours, and from the adorable devil-may-care smile on his profile picture below:
But Cracked staff also know him as someone who's taken a pass at every piece of content published on the site since 2007. If Cracked rolled credits on every article, podcast, video, and business transaction, Jack's name would be on everything. And even if none of the above was true, even if Jack was a distant boss who never put his stink on edits or writing jokes or participating in meetings that vetted every single entry on every single workshop article even up to the day I'm writing this tribute, he'd still get credit for creating a work culture that compelled me to write a tribute in the first place. And that's a big deal.
When I was first hired as a Cracked editor in 2010, I braced myself for the competitive, testosteroney, maybe misogynistic conference call meetings that would surely be a part of my weekly routine. That expectation wasn't a reflection of the guys I was about to work with, they seemed nice in print -- which was how all of my interactions up that point had occurred -- it was based on how I thought guys functioned together in groups. And that misconception was just based on ... high school, I guess?
My first day came and went and I've never once had a chance to put my foot down about anything. The culture that Jack set up was collaborative and kind and every person's opinion carried weight. We consulted on everything from article titles to cute nicknames for each other. "Oh but Kristi, surely there were some sexist moments ... " No, I've got nothing. Absolutely nothing.
Speaking of segues, I'm really going to miss the Jack/Jason Pargin (aka David Wong) partnership. For those of us who work across the country, Jack and Jason tag-teamed this operation. In my department, Jack was in meetings on Wednesday/Thursday, and Jason was in meetings on Tuesday/Friday. And in between, one of my jobs was explaining to Strict Dad what Cool Dad liked about the stuff we approved last week. And unlike most real parents, Jason and Jack have such a deep respect for each other's opinions that all you had to do was say, "Jason (Strict Dad) liked this entry" and Jack (Cool Dad) would say, "That's all I need to know. Now go get some ice cream and watch cartoons, you've worked very hard today!" And I would go get ice cream and watch cartoons, for indeed I had worked hard that day.
I've loved watching how these two people with completely different backgrounds, who only met in person a handful of times, built our brand and made it excellent. Right after the picture below was taken, we all retired to the Cracked building to watch Dennis Rodman's movie about little people who play basketball. It was called The Minis. It was one of my favorite days of ever.
Another thing I'm going to miss about Jack is that we kept finding out new things about him. Once, someone told me his dad was an NBA coach. Anyone else would have led with that information, but not Jack. When he started the podcast, he'd intro the show with intensely thought out pieces of music that he personally curated into a Spotify playlist. "Oh snap," I realized. Jack's real thing is hip hop, somehow. Who knew? Does everyone know that one of Jack's favorite live performances is Robyn's joyfully weird "Call Your Girlfriend" on SNL? Watch that and then tell me you don't like Jack. I dare you.
The model Jack set up was that everyone at Cracked can all do anything we want -- host shows, join podcasts, pitch videos, write fact-based articles or opinion based columns, contribute ideas on workflow or streamlining our process, recruit talent, all of it. And that wasn't weird for him because he could also do all of those things.
Thank you for everything you've done for us, Jack. The ideas that came out of your head helped millions of people around the world, and me and my family personally ... which is the most important thing, in my opinion. I will click, like, subscribe, and share everything you do in the future, forever and ever, Amen.
I'll never forget the day Jack O'Brien first pitched me the concept of Cracked.com.
I was treating him to dinner to tell him about my own idea for a list-based, research-driven comedy website featuring articles, videos, podcasts, and personal experience pieces written in the inimitable style of Robert Evans, a writer I had not yet heard of at the time. As I picked at my side salad, Jack mulled over my pitch, mouth agape with surf n' turf and caviar.
"It sucks," he said at last. I could tell he'd really thought it over because he finished a $300 bottle of wine before responding.
I was crushed by his assessment initially, but when Jack said he liked my moxie and offered me an unpaid intern position at HIS new website Cracked.com over his third dessert, I knew I'd hitched my star to the right wagon's coattails. Nearby, Pixar executives murmured about robots servicing the obese.
Cut to a decade later, and the time has come for Jack to move on to bigger and better things. I must un-nestle myself from beneath his wing and take flight on my own, as he informed me at our recent Fogo de Chao luncheon (my treat). As I picked at my side salad, I was filled with appreciation for all that my time at Cracked has allowed me ... it's the dojo where I honed my comedy skills, met the network of friends and colleagues that will either propel me to artistic fulfillment or stab me in the back at a key moment, and it will always be the locus of a defining chapter of my life, both personally and professionally.
Cracked is, for me, a parcel of memories and a time and a mental space, and one I know I'll return to often. Thank you, Gatekeeper, for admittance into the playground. Once your son succeeds you, I vow to serve him as viciously as I served you, if not moreso. Further, I forgive you for using one of the swords the Fogo de Chao waiters use to carry meat to cut my clothes off. In retrospect, you were right; it was pretty funny.
Again -- thank you, Jack O'Brien. Cracked was my clown college, and you were its crusty dean. Now that you're leaving, I can finally tell you: It was US who assembled a VW bug in your office that time. SIGMA TAU HOUSE RULES!
1. If Cracked.com was a country, Jack's face would be on the money.
2. I'm keeping this short because a legion of other Cracked writers have messages here too.
3. Do me a multi-step favor:
a. Get past my message, to their messages.
b. Notice that their messages are excellent pieces of writing.
c. ALSO notice that the high quality of those messages is an intrinsic tribute to Jack, in and of itself. Because he helped cultivate every single one of us as writers (and more). And I like that this page is tributes all the way down, so to speak.
Mack Leighty aka John Cheese:
Have you ever heard someone use the phrase "true friend"? Specifically, when they put the stress on that first word? They're doing that for a reason -- because most people know that the collection of people they hang around are one thing ... but a true friend is on another level. They're social rarities. They're something to be admired. Sought after. Cherished.
Most people think a true friend is someone who accepts you as you are. Someone who puts up with your bullshit and doesn't shame you for it. I don't agree with that.
A true friend is someone who sees your potential and then pushes you past it. They won't ever let you settle for mediocre because they know you're capable of more. When everyone else is kissing your ass and telling you that you're doing a great job (with work, relationships, creative hobbies), a true friend will say, "This is a great start, but you can do better. Let's talk about how."
Jack O'Brien never let me settle for "acceptable." Don't get me wrong -- if I did a good job with something, he let me know it. But if he saw something I wrote that didn't reach or exceed what I was capable of, he pushed. Not just for the company or for fucking clicks. He pushed because he saw something in me, and if he let me put out work that wasn't my absolute best effort, he was allowing a massive disservice to myself.
Jack O'Brien, you are a true friend, and I'm going to sincerely miss you. Without you, there is no John Cheese. No Daniel O'Brien. No David Wong. You built this. You built us. I will be forever grateful for that, and I promise that even after you're "shit on people's lawns and not do jail time" levels of famous, I will continue to do what you taught me: to never, ever settle for anything less than my absolute best.
One of the worst things that can happen to a smart, original comedy is massive box office success because it means the jokes become so entangled in our cultural consciousness and the catchphrases such a part of our everyday lexicon that the public exhausts them prematurely. You can never look at Wayne's World or Airplane! with fresh eyes again because they are such an intrinsic part of who we are now that the jokes don't even sound like jokes anymore.
This is also my going theory for why Jack O'Brien isn't funny.
That doesn't mean he wanders around the office saying "Alrighty then!" or asking babies if he makes them horny. I mean Jack helped change the entire landscape of humor on the internet, bending it to match his own comedic sensibilities and, from that point forward, we've all just been retelling the same joke he created over and over. It is not hyperbole to say that Jack saved Cracked. He took a stale magazine and turned it into a comedy website that convinced the world of the Pixar Theory, that Teen Wolf is a race relations parable, and that Tom Hanks has some sort of urine rider in all of his film contracts. In 2017, jokes about the honey badger not giving a fuck, or how Thomas Edison's a dickhead feel, so well worn they might as well be factory-issued jokes that come standard with a brain. But the truth is that those only bubbled up into the collective consciousness because of the website that Jack built.
Of course, not all of his pop-culture seeds found purchase. Jack worked briefly in championing the stereotype that Italians are incredibly tiny, like human shrinky dinks and spreading the conspiracy that G.I. Joe was responsible for the Iraq War. Look, not everything in the pan is going to be gold. But he's got a better eye for what's interesting and funny than anyone I've ever met.
He's also taken a lot of shit from columnists over the years without censoring any of them. We've painted him as everything from a gun-nut pill-addict to, worse, a milquetoast square ruining everyone's fun. But beneath it all, everyone at Cracked knows that we are only here because of him. He gave us this platform, he made us each better writers and I am eternally grateful.
In one of the last articles he wrote, Jack talked about how our history books are wrong; European settlers in America didn't actually carve a life out of the untamed wilderness.
"The pilgrims couldn't believe their luck when they found that American forests just naturally contained an ecological kaleidoscope of garden plots ... Frontiersmen who settled what is today Ohio were psyched to find that the forest there naturally grew in a way that 'resembled English parks.' You could drive carriages through the untamed frontier without burning a single calorie clearing rocks, trees and shrubbery."
The truth is that Native Americans did all the boring hard work clearing trees, aerating soil, planting seeds, and tending crops before getting wiped out by plague, so when settlers arrived, they thought it was gifted to them by God. I think that's a pretty good metaphor for what Jack has done for everyone who has and will ever work here. Also because Jack is dead to me now. He will always be the best Editor-in-Chief the site has ever had (which is like an Editor but with more feathers in the headdress).
I belligerently entered the Cracked Writer's Workshop about six or seven years ago. For those unaware, it's an adjacent forum where literally anyone can pitch article ideas for the website. It was extremely easy to sign up and pitch my first article, as evidenced by how drunk I was while I did it. At the time I was living in LA, sleeping on a dirty yoga mat in an apartment I couldn't afford with my seasonal, minimum wage job. Needless to say, I was angry -- and that booze-churning ire translated into utter dickheadedness in the workshop. And so my introduction to Cracked was to act exactly like the kind of petulant jackalope Future Me would boot from the forums. My first pitch was immediately given patient and helpful feedback by another forum member, which I promptly and snarkily refused to follow (I was a genius, after all). I was then informed that the person giving me the feedback was Jack O'Brien -- Editor-in-Chief of Cracked.com.
To reiterate, I drunkenly wandered into Cracked's digital front office ... and was immediately greeted by the guy running the place. Anyone on the job market right now knows what a jaw-plummeting miracle that is. But for Jack, it was just how things ran. He helped design a system where elitism couldn't thrive, and people were judged solely by their knowledge and talent. Years later it would also be Jack who first called and offered me a job as an editor for the site. At the time, I was still working minimum wage gigs in dishwashing or food delivery. I had no formal background in writing, but it didn't matter. He hired me without glancing at a resume or even seeing my face, instead trusting the quality of my previous writing. Can you imagine that?
In a single phone conversation, Jack changed my future. And when I finally met him face-to-face at the office, he was the coolest and nicest person in the room. Not to mention a class act, total clam magnet, and with a sweater game that was fucking paramount. I haven't known him personally for very long, but I am the product of his leadership and kindness. Now, saying goodbye, I can only wish him the best of life, and try to make him proud of what he's created here ... and not like, accidentally hit a bunch of people with my car or start a murder cult where we stab the elderly with crystal shards ... even though that would be a cool thing to stab people with.
Thank you, Jack.
When I first met Jack O'Brien, he was taking a Bolivian Trainride in the bathroom of Armar la Gorda, a dusky Latin Satanist gay bar on the corner of 66th and 6th. Now, for those of you unfamiliar with the maneuver, a Bolivian Trainride is when one man sets up a line of cocaine on his erect-
What? I was gonna tell them he was the conductor!
Ugh, my stupid new boss is telling me these are "inappropriate lies."
You know who never said that to me? Not even once? Jack O'Brien. I've told more inappropriate lies about Jack O'Brien than I have in every police statement I've ever made, and he's never asked me to stop. He's never even asked me to tone it down. My family sure tells me to stop. My friends tell me to tone it down. But when I get started on another of my "junkie Baron Munchausen" tales, the only thing Jack O'Brien does is rotate his finger in the air, as if to say "turn it up."
Seriously. In my rare moments of self-reflection, when I realize how terrible and irrelevant my writing is, Jack takes a look at it and tells me it's great. Or if it's not great, he tells me how to make it great. He's never introduced the specter of marketability into our conversations. He's never broached traffic numbers or bemoaned the advertisers. He rotates his finger in the air, and I turn it up.
I used to ask other people if they saw him, too -- I was so certain he was a hallucination. Who on Earth would support me like that? Especially when I repay him with terrible lies that only serve to cast dispersions on his character? But no, Jack O'Brien is real. And he is the best editor that has ever lived.
Or rather, I suppose I should say, "was the best editor," because he's dead now. It all started at Armar la Gorda during the Rough Trade Show. Jack was dressed head-to-toe in bright yellow latex, swinging from the ceiling like a magnificent bondage pinata when-
What? God damn it, what is appropriate then? I loved this man! You let me eulogize him in my way!
Lots of times when Cracked comes up people think of the old magazine. Jack always hated that, because he had a grander vision of what the brand could be: a source of information and comedy, crossing various media, and most importantly giving the audience their money's worth in references to Back To The Future. Jack worked harder than almost anyone I've ever met for YEARS in order to put Cracked on the map with a fresh, new public perception, and it WORKED.
Francis of Assisi once said, "Start by doing what's necessary; then do what's possible; and suddenly you are doing the impossible", which I have to assume is accurate because it came from brainyquote.com and I trust them. Also, that quote reminds me of how much fun and greatness has come from Jack's unabating efforts to always keep our ship sailing ... into the sun? I don't know anything about boats. Lastly, on a personal note, I simply have to thank Jack for making me a better creator and artist than I was when I started. I can certainly say you will be missed, but you'll no doubt make things great during your future pursuits. Rest In Peace.
Jack is like a cool dad to me, though I don't think he will probably like being called a dad. But he's like a dad because my dad also used to work in an office in the corner and also I wanted him to approve of my work but also I don't want him to know that I want him to approve because that would be trying too hard. I think the clearest example I can think of for this is when I shot that mushrooms video in our office with Robert Evans.
There was a moment when I was tripping out of my mind in the Cracked parking lot at 11 PM when I confided in our director that I didn't want to "let Jack down." I think I was afraid that if I got too high it would make me look bad and thus Jack would disapprove. Then in my performance review this year Jack actually said he liked that video a lot, so it kind of worked out in the end. I'm so lucky to have worked for Jack. I think he has to change his name now so that none of us have to see Jack O'Brien working for a company that is not Cracked. Maybe Rupert. I could see him as a Rupert.
In 2014 a few of my friends in Seattle invited me on an out-of-the-blue road trip down to Los Angeles. Since I was "working" as a freelance writer, it was no problem for me to drop everything and come along. I'd never been to LA and I was pretty sure the Cracked offices were there. Since they accounted for about half my income, I told them I was going to be in the neighborhood and asked if I could drop by. They said yes, and when I got there, Jack walked up, shook my hand, and asked if I would mind walking with him into, "this room over here."
Unlike most people who go to LA and are invited into mysterious rooms by strangers, I wasn't murdered. Instead, Jack hit me with a surprise job interview. The only part of it I remember was apologizing for the weird stain on my t-shirt, which they probably hadn't even noticed. (It was mustard. Weird stains are always mustard.) Three months later I had moved here and was working in a building with air conditioning for the first time in my life.
I'm self-conscious because this is mostly about me so far, but the point is that it was great working for Jack because he always saw the potential in people -- even when we couldn't see it ourselves -- and then trusted us to develop it. It was a huge risk to throw an editor job at an unemployed guy with the forum name "Antagonasty" and, as far as he knew, zero clean t-shirts. I hope he feels like it paid off. It certainly changed my life, and I don't know how I could ever repay him. Maybe with, like, three funny paragraphs in a Cracked article. That'd probably about do it.
Jack, thank you so much for welcoming me into the team and for your guidance. I've greatly enjoyed working with you. I'll miss you, Jack. Please come back soon from buying cigarettes.
I had no idea how to write a farewell thing for Jack. I could write about how he plucked me from obscurity and gave me a job without having ever met me or even seen my face, but that story is mostly about me. Jack's in it, but only like one or two scenes, like Marlon Brando in Superman. I also didn't want to write anything too emotional, even though I could, because I pretty much owe everything I have to this ridiculous job Jack decided to give me. So instead, I decided to list a bunch of interesting things I learned about Jack over the course of working for him for the past eight years. I call them Jack Facts(TM).
-- Jack is a tall man. Only Michael Swaim is taller, but Michael is taller than everyone so I don't think that should count against Jack's tallness.
-- Jack's real name is "John." You see, "Jack" is a nickname for "John," although how and why will forever remain a mystery to me. They're the exact same number of letters and they take the same amount of time to say. They're two completely different names. Although, the majority of action movie characters are named either Jack or John. Like, John Matrix in Commando is also technically Jack Matrix, and John McClane could easily start telling people to call him Jack McClane and it wouldn't be that weird. So maybe that's it. Anyway, I've never seen Jack shoot a gun.
-- Jack is the tidiest eater I've ever seen. He eats like he's trying to be polite to his food.
-- Jack almost always has his earbuds in. To be Editor-in-Chief requires you to constantly be consuming information, and I've heard rumors that he has a text-to-speech program that reads him the article pitches for the day so he can multitask. However, it is also possible that Jack isn't listening to anything, and just has the earbuds in as a power play. Either way, it's bold.
-- Jack once announced in a meeting that he has no idea whether anyone at Cracked has been to college. This was the most important piece of career advice I have ever received.
-- Jack does not care for the film Prometheus.
-- Jack has an intimidating collection of puffy jackets. Actually, now that I'm thinking about it, it may just be the one jacket, but it's a remarkable piece of clothing.
-- Jack handled a lot of the less fun jobs at Cracked so that the rest of us would be able to work on the stuff we were passionate about. In fact, he had so avoided the spotlight in the early days of Cracked that I initially assumed he was more of a figurehead, like the Queen of England, or Ted Turner. I also briefly suspected that Jack and David Wong were the same person. Neither one of these assumptions were correct, although I have never seen Jack and the Queen of England in the same room.
-- Jack's office nicknames are "the Jacker" and "Dad Boss Jack." He definitely hates at least one of them.
-- Jack called my wife when I was hospitalized last year to see if there was anything he could do to help. He didn't have to do that.
-- Jack founded Cracked.com and gave it his undivided focus and energy for an entire decade. He hired people he believed in and trusted to care about the site as much as he did, and now he's leaving it in our hands. There's no bigger sign of trust than that. So while I don't want Jack to leave, I'm glad he feels like he can.
-- Good luck, Jack. Thanks for everything. We'll try not to burn the place down, unless we have to because of some kind of Timecop situation where blowing up Cracked.com prevents Hitler from becoming the lead singer of Aerosmith.
Jack O'Brien has been my boss for most of my adult life. He hired me on as an unpaid intern back when I was 20, and almost completely worthless. Now I'm 29, and to be honest the idea of going into work without him at the head of things seems incomprehensible. It's not that Jack is a super hands-on boss. He's exactly the opposite: When I transitioned from a freelancer to a full-time staffer in 2013, Jack immediately took most of my job away and basically said, "Find new stuff to do."
When I decided I wanted to try out a new type of content that eventually became the Personal Experience article section, he told me to go for it. He never told me how to do anything. He just told me if what I was doing worked. I can't imagine a better boss for a young writer to have. With Jack, I never felt like I was writing to fit a prompt, or hit some arbitrary metric. I had the freedom to experiment and just enough guidance to know when my experiments were dumb and likely to end in a flurry of lawsuits.
I'm struggling to end this without getting too mushy. Jack was a great boss. His mentorship is probably responsible for most of my marketable skills. I'm excited to see what he'll do in the future but, holy shitting dicknipples, it's going to feel weird here without him.
Jason Pargin aka David Wong:
This is going to shock some of you: I'm not an easy person to work with. Or to do anything with, really. I'm not an easy person to talk to, or not talk to. I'm not even an easy person to be a stranger to -- ask the Comcast customer service rep I started yelling at last week. Above, Kristi described early Cracked as a kind of tag team between Jack and I (at one point we were the only two dedicated employees) but the spirit of respect, humanity, and kindness that has been established here sure as fuck didn't come from me.
I'm not going to dig into the whole sordid tale of the brand; the 59-year history of Cracked is long and stupid and I wasn't here for most of it. It existed as a poor man's Mad Magazine for almost half a century, plugging along with a third of Mad's circulation. The publication finally folded, got bought by some investors, and relaunched as a glossy humor magazine. Then that one folded and all that was left was its website. In 2006, that site was snapped up by an internet company for about the price of a decent house, one of hundreds of domains they were in the process of acquiring.
So, while unsold issues of the magazine were getting pulled from shelves and pulped, the website was quietly growing. That was because of Jack, another genius named Jay Pinkerton, a college intern named Daniel O'Brien, and a bunch of freelance writers they'd cobbled together. In 2007, Jay got hired away by Valve and helped write Portal 2. (He's still there, ask him if he's writing Half-Life 3, he probably loves that!) Jack was allowed to bring on an assistant editor and he made his first hire: Me, a blogger in the rural Midwest whose day job was working in an insurance office processing medical claims.
My perception of comedy on the internet at the time was that it consisted of A) some wonderful satire like The Onion B) lots of frat-boy "bro" comedy ("10 Ways To Tell If The 'Nice Girl' At The Bar Is Really A Skank") and C) bitter "rant" comedy -- dudes playing over-the-top angry characters raging at inconsequential annoyances, talking about how this movie or that raped their childhood. Jack wanted Cracked to be different. At my interview, I got the sense he was trying to build something that would appeal to people like him -- smart, decent, optimistic. If you think it's easy to do comedy like that, you've never tried it. It's way easier to just shit on easy targets.
So, Jack inexplicably brought me on board ahead of other much, much more qualified candidates and together we found that the world had been waiting for something exactly like this. The old Cracked magazine, at its best, averaged something like 80,000 readers a month. A couple of years into the job, Jack was writing individual articles that would reach a few million.
But that's just traffic stuff, it's not proof of anything -- there's a video on YouTube of a drunk getting his dick caught in a quadrocopter that has ten times as much traffic. So let me say this instead: I've worked with Jack for about ten years and never saw him really lose his temper, or get jaded about this whole thing, or succumb to the constant, overwhelming pressure to turn to the internet's dark side. I shared many a Yahoo Messenger chat session with him at three in the morning, the two of us exhaustedly trying to fix an article hours before it was set to go live to millions of readers, trying to seize an opportunity to do something great. Through all of that, he was never petty, never mean, never tore people down. Ever. Jack at his most exasperated resembles me when I'm on vacation.
Cracked kept growing, a decade later boasting millions of readers, dozens of employees and an ocean of contributors. It was bought last year by E.W. Scripps for nearly $40 million. But that's just more numbers, who cares. What matters is that through it all, the beating heart of the operation was Jack's intelligence, decency, and optimism. He had an unwavering belief that you can succeed in this world by appealing to the best in people, that the audience was naturally curious, to the point of being willing to see their prejudices proven wrong.
Jack is leaving Cracked, for a job that hopefully doesn't constantly feel like trying to carry a wedding cake across an icy parking lot. I understand completely. He has a family, I think, and eventually, creative people just want to try new things. Orson Welles didn't rest on his laurels after Citizen Kane; he went and voiced a great Transformers cartoon. Dennis Rodman left a Hall Of Fame basketball career and made Double Team with Jean-Claude Van Damme and later, The Minis. Bill Cosby left The Cosby Show and went on to become a renowned author.
What's good about Cracked will not leave with Jack O'Brien. He hand-picked this team, one member at a time. We're all in it for the same reason, we've all helped this grow far beyond what any of us expected back in those early days when Lex Friedman was desperately coding the site on the fly and we could feel the bosses at Demand Media slowly realizing they had something really cool on their hands. We have no plans to let it die or let it get even slightly worse. Cracked is a proverbial brick shithouse of entertainment.
As for what Jack has done for me ... let me put it this way: It kind of doesn't matter what happens with the rest of my life -- I will always know I was a part of building something special, and that can't be taken away from me. It will be the first thing mentioned in my obituary, no matter what terrible things I do in the future, and it's all because of Jack. I can't tell you what that means to me, because I can't summon the words to convey it. I'm not that good of a writer.
I hope Jack does great at his next thing, I hope we do great without him, I hope we've somehow made the world slightly better than it was before and that we can continue to do that. That's all we can do. Any of us.
For more of Jumpin' Jack Slash Fic's greatest hits check out Yer Gramma was Built Like a Brick Shit-House In Her Day and The 5 Greatest Things Ever Accomplished While High. And let's not forget Jackula Prince Of Darkness And Sometimes Thieves' monster successes 6 Ridiculous Lies You Believe About the Founding of America and Yer Gramma was Built Like a Brick Shit-House In Her Day.
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