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Disgusting Sneakerhead And Lovely Human Being Sam Woolley Is Leaving Us

Today is Sam Woolley’s last day at GMG; after six years of brilliantly illustrating across the network’s various sites as well as hosting the occasional Funbag and sharing the odd harrowing view into his personal care routine, he is now heading off into the hereafter. RIP Sam. Here’s how we’ll remember him.

When I met Sam, he was working at what he described as a sort of sweatshop factory studio, mass-producing paintings for hotel rooms. That’s one anecdote Sam will mention about his past. There are many. Another is that he has spent six Christmases with Keanu Reeves’s mom. We met and chatted at the Chinese restaurant bar near the old office, and anyone who has met Sam will know that it quickly became apparent that he was going to be easy to get along with.


We’ve spent the last six or so years working together, and he has been the nicest, most genuine, and hardest working person I can imagine working with. He’ll tell you about his family, and it’s clear how much they mean to him. He’ll ask you about yours, and remember details you forgot that you mentioned the last time. Over the years, I’ve watched him develop as an artist and as an ever-present staple of this company.

Sam also has a weirdly obsessive relationship with designer sneaker culture that I’ll never understand.


Megan Reynolds

Being actually nice and saying genuine things about someone who is one of the nicest and most earnest people I know is hard because it makes me look soft and not like a friggin’ bitch—a shame. However, all I want to say about Sam is that he IS the nicest person I have met in some time and will be missed. Also he’s GREAT at what he does AND ideally, this entire post will make him cry.


Dodai Stewart

Sam Woolley and I first “bonded” over me scolding him for his absolutely offensive and abhorrent ketchup drawing of a dick, but that story has been told. What’s important to know about Sam Woolley is this: He’s The Worst. But also The Best. Confusing? Yes. Maybe because like me, Sam Woolley is a Manhattan-bred Gemini. The problem is, unlike me, Sam Woolley is a jerk with a microscopic attention span and disgusting sense of humor, a hypebrat who will clown your sneakers/jeans/t-shirt, a Vangelis fan who thinks he’s “a handsome motherfucker.” I can’t even tell you how many times he’s erroneously informed me how good looking he is. It’s annoying when he calls me “son,” eye-rollingly dumb how much he sweats Nike Air Maxes, and his dating advice is vomitrocious. I love him dearly and wish him the best.


Billy Haisley

Sam Woolley has a 5-year-old’s attention span, a 10-year-old’s sense of humor, a 15-year-old’s romantic predilections, and the lifestyle of a man who believes he is and will forever remain 20. Combined with these youthful attributes is a fierce loyalty, an extroversion that is inviting rather than off-putting, a nearly complete absence of self-consciousness, an effortless charm, a genuine kindness, and a knowledge of and confidence in and comfort with exactly who he is. He’s like that impossibly cool art kid in school who got invited to every party and when he showed up to yours you were delighted because of what his friendship said about you and what his patronage meant for the unforgettably wild night you were in for. Yes, I am saying Sam Woolley has never grown up. I am also saying that even though he is old enough to be my older-but-weirdly-too-young step father, being friends with him has kept me from growing up too much, too.


Patrick George

When I told Team Jalopnik that Sam was leaving, they were shocked and heartbroken. Several of them started crying. Mike Ballaban threw his head back and screamed at the sky, openly cursing God. Kristen Lee threw a chair out a window.


This is because Sam is about the nicest and hardest working human being on the planet, and he’ll be desperately missed around the office. Additionally, for whatever reason, Sam ended up doing probably most of Jalopnik’s artwork over the past couple years. His creative work never failed to blow us away, and it added prestige, gravity and even comedy to our stories. Gizmodo Media has far and away the best art department in all of digital media, and Sam’s considerable talents—and commitment to perfection—were and are a huge part of that.

I wanted to look back and pick out my favorite Sam artwork for Jalopnik, but that proved hard to do because a.) his shit always ruled and b.) he did just a ton of work for us. I’ll go with these two: One was an especially memorable portrait of Faraday Future’s beleaguered billionaire founder/quasi-CEO, Jia Yueting, and the other was a ton of cars stacked in front of Detroit’s courthouse for a story we did about subprime car loans.


Sam, you’re the best. Good luck at whatever’s next. You’ll always be a friend of Jalopnik.


Ernie Deeb

Sam is a grown ass man who outgrew hypebeast culture but never outgrew the clothes. He has poor taste in music and even poorer taste in sports teams. We have so much in common.


I’ll miss his pointless stories about Cormega and our love-hate relationship with the Knicks and the Mets. Sam, believe in yourself and one day your NBA 2K19 MyCareer character will win Finals MVP.

Chelsea Beck

Imagine you’re at a funeral and everyone’s really somber and you’re of course dreading this whole day but suddenly you see him— he’s in the back corner sucking on a vape totally charming the pants off the 90 year old undertaker. The whole thing is a little inappropriate for the vibe but no ones mad because the guy is just *so* charismatic. That’s Sam.


We’ve never been to a funeral together but even on my darkest Monday he’s always there with a smile and an earnest offering of something totally legal to pick me right back up again. He’s the charming, irreverent, deeply inappropriate uncle you’d use as your only call from a lonely jail cell and he’d convince the cops to let you out scot-free.

When Sam enters a room he leaves with two more friends (and their moms’ phone numbers.) He’s a guy I want my yet unborn children to learn nothing and everything from.


Sam, I know allllll of you and your personality will have a new home but I better still be getting the occasional midnight phone call while you drunkenly describe Manhattan from a citi bike. Love you, Uncle Sam.

Elena Scotti

Here is a thing I made for Sam : ( RIP


Kate Dries

Sam somehow manages to pull off being a man of [AGE REDACTED] who cares too much about sneakers, which is the biggest compliment I can bestow upon someone. He also has a lovely sweater collection.


Samer Kalaf

Sam, thank you for always being willing to split a side order of fries when we would get lunch at that sandwich shop. You knew that I wanted some fries but not all of them, and I appreciated your generosity. The stuff you did with the art was also nice.


Barry Petchesky

Sam Woolley is the only dude in this office who will strike up a conversation with you while in the bathroom. You can be washing up at the sink next to each other, or side-by-side at the urinals, or one of you entering a stall the other one’s leaving, and he’ll happily start talking about the Yankees, or compliment your shoes, or gush about some new co-worker’s talent, and he’ll do it in a normal voice, as if casually chatting while one or both of you have your dicks in your hands isn’t a weird thing to do. And because Sam is just the kindest, most earnest person, it’s not.


Sarah Dedewo

Sam is an amazing soul. One of the best that I’ve met. He sees the best in every person and situation. He’s always believed in me and encouraged me whenever I’ve felt like giving up. He is a funny, smart and talented fellow that I will always look up to. I’m so glad he is in my life!


Tim Marchman

The one thing that pretty much everyone who has worked at Gizmodo Media Group or Gawker Media will agree on is that the company’s best editorial minds are in the art department. It isn’t just that their work is often what marks the difference between an okay story and a good one, or a good one and a great one, but that they are better than anyone at understanding the essence of what a writer is trying to say, even when the writer isn’t quite sure what that is. I’m hardly the first person to say it but it remains true, and a lesson a lot of writers and editors learn here: If they can’t do a great illustration, that means something needs to be fixed in the story.


When I started here, there was no art department; there was just Jim Cooke, a singular and singularly exacting visionary with a distinct approach and ideas about how things were to be done. The difference between then and now has largely to do with Sam Woolley, who, by joining Gawker Media as a staff artist and adapting brilliantly to the impossible task of creating and maintaining a visual language that was distinctively his own while working equally well with the copy of dozens of writers across more than a half-dozen sites and areas of coverage whose work ran from the impossibly stupid to the impossibly sober and who always needed things done an hour ago, turned a one-man operation into a department.

I could go on about his flair or clean lines or how psychedelic he can make a black and white illustration or just how fucking funny most of what he does is—I defy you not to laugh just looking at these—but Woolley’s work is so brilliant, and has been so brilliantly right for GMG, because he is interested in everything. The trick in being equally adept with sports and music and politics, with half-assed jokes and investigations reporters have poured months of their lives into, and with all the rest of what comes with the job he’s done here, is to not have any tricks and not try to fake it; you have to really know things cold and you have to care. It’s a sad thing that Sam Woolley is dead now.



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Jim Cooke

Art Director — Gizmodo Media Group |,,,,,