Sean Sullivan: The Art of the Impossible

The man behind "The Impossible Cool" talks style, art, and well-dressed men.

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Image via Complex Original
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The man behind The Impossible Cool talks style, art, and well-dressed men.

This feature is a part of Complex's "Tumblr Generation" Week.



Written by Jian DeLeon (@jiandeleon)

In Sean Sullivan's world, legends never die.

Unfortunately, that isn’t the case in reality. Over the years, Sullivan has garnered a respectable online following on his Tumblr, The Impossible Cool, which is known for its simple black-and-white photos of actors, musicians, and other notable figures who may have burnt out, but certainly never faded away. Photos of Joe Strummer and B.B. King are sandwiched between portraits of Robert Redford and Thelonius Monk. The stark white background and minimal design almost make the carefully thought out site seem like a photo album of the best-dressed people of all time.

Three months ago, the photographer left his New York City home in a 1972 Mercedes 280SE. American leather luggage company Ghurka has paid him to go west and photograph their fall offerings. When he has downtime, he documents his journey on Ghurka’s Rangefinder blog, touted as a “traveling photo and video essay that spotlights the best of the American road,” and named after a Ghurka bag specifically manufactured for Leica, a brand name that makes camera nerds salivate. It’s also built on the Tumblr platform.

I always wanted to convey the spirit that you don’t have to do a certain thing or make a certain amount of money to be 'cool.'

“I’m looking at Tumblr these days as more like an entire project as opposed to daily content streams,” says Sullivan. “I like the idea of launching a Tumblr that’s almost already ‘done’ so people can go through the whole experience all at once rather than wait for new content.”

Like many popular Tumblr users, Sullivan has been able to funnel his site’s success into lucrative opportunities, and for him that means putting his photography skills to use for brands like J. Crew, Wolverine, and Cole Haan. In fact, these previous projects are what piqued Ghurka’s interest to hire him for this campaign. While a lot of planning went into the cross-country expedition, Sullivan still runs into some snags. For one, his vintage ride may not survive the odyssey.

“A 1970s Mercedes isn’t meant to be driven across the country,” he laments. “When those cars were made, speed limits were like, 45 miles-per-hour probably. Blasting down highways at 80 miles-per-hour in a Mercedes that was built before I was born is just… it’s a lot,” admits Sullivan. “By the time I made it to Louisiana, I was looking at a map of the United States and staring at this massive drive across Texas. The thought of anything happening to that car in the middle of nowhere bugged me out.” 

Sullivan is also worried that the Mercedes’ old-school security systems won’t keep his camera equipment safe. So the decision is made to switch to a rental car for the trek’s next phase—a decidedly less cool Ford Edge, a mid-size SUV with rounded edges and a wide grill that looks like an amalgam of an Autobot and R2-D2. What it lacks in street cred, vintage appeal, and Tumblr-ready photogenicity it makes up for with amenities like cruise control and satellite radio.

It’s actually a blessing in disguise, because now the 34-year-old photographer can focus more on finishing the campaign than worrying about things like blown gaskets and overheated carburetors. As Sullivan wraps up the last leg of the tour—a long drive from Northern California all the way to Los Angeles—he takes some time off the open road to talk about his other journey: How he went from a Tumblr blogger to a rustic photographer with a style all his own.

Do you think your experiences with the Mercedes are a microcosm for that whole “life on the Internet in photos” versus “real life” aspect?
Oh totally! You can go through Tumblr and see these beautiful images of old cars. The first car we were going to use was a Land Rover Defender, and it was the same thing. They look amazing on the Internet, and then when I test-drove the thing, it was like driving a tin can. The seats were metal, they didn’t recline, and the thought of hitting 120-degree weather in the middle of the Mojave Desert was the first reason why we didn’t it. Yes, they look cool, but it reality, after you think it out, you realize you’re living in a bit of a fantasy.

How long have you been into photography and video?
I started five years ago. I worked in the film business for a long time. I worked in the location department and moved up into the production world. I got burnt out on that. I’ve always taken photography seriously; I even went to school for filmmaking. I got sidetracked after college and decided to stop working and go out on my own.

When did you first move to New York?
I think it was the summer of 2003. I grew up in Philly, and I graduated high school and then moved around. I didn’t know what I wanted to do so I traveled for two years, came out west, spent some time out here,  then ended up back in Philly. I went to college but didn’t finish, so I left and moved up to New York.

I always visited New York when I was younger because Philly was so close. I was a skater and that was one of the other cities we went to skate, and write graffiti. I’ve lived in New York for the past ten years. I plan on moving to California, but I’m keeping my place in New York. I want to head out there and really get my feet wet. There’s a lot to do out in LA, so after this trip I’m going to give it a try.

When did you join Tumblr?
I joined it when it first launched, sometime around June 2007. I had a Blogspot at the time, but didn’t want to do Wordpress because it felt dirty. This really started out as something I just did for fun. Tumblr at that time was the easiest platform to use: It was very user friendly.  Another thing was that I hated the comments on the other platforms. The feedback was negative. I wanted to keep negativity away from the site. I didn’t want people to talk shit about who slept with whom. I wanted a site that really presented the people.

So there was a sense of purity about it?
Exactly! You’re really just presenting it to the people. You’re not offering an opinion. You’re just giving it to people.

Was Tumblr a little bit easier for you to use as a visually oriented person?
Oh yeah, totally. Whenever I mention the beginning, I always have to give a shout to Justin Saunders at JJJJound. In my memory, he was the first person to actually do the never-ending picture stream.

Yeah, Justin is a pioneer in that sense.
Totally! He was doing that before Tumblr was around. I always thought that was super cool because you can start to create stories inside this photo stream—which a lot of people do now. So yes, being a visual person was also great for the Tumblr platform.

Was the idea always to post these iconic photos of celebrities?
Actually, that came from when I first moved to New York. I was working for Paul Smith in the suit room, back in the old haberdashery on Fifth Avenue.


How did working at Paul Smith influence The Impossible Cool?
I always liked the aesthetic of the ‘50s, ‘60s, and ‘70s. I had an uncle that was Bruce Springsteen's tour manager back in the day. I was always rifling through his photos of The Allman Brothers and whoever Springsteen was playing with. I always liked that stuff. My great-grandfather was involved with Kennedy so I used to see family photos of that too. I loved the stories being told by these older photos. Over the years, I collected them and put them into a folder on my laptop. 

When I was working at Paul Smith, there was this huge board in the  suit room—it was like analog Pinterest. The suit room there isn’t Savile Row, it’s a bunch of misfits that hang out in expensive suits. I worked with this guy named Clyde. He's a movie buff, so we’d talk about film, and we would post people up on this board. Men like Serge Gainsbourg, McQueen, Newman—people that are now up on my website. It wasn’t an inspiration board, we would just throw up pictures of these guys as homage. That, combined with already having these photos on my computer, led to the Tumblr. I thought no site out there was paying proper respect to these people who'd been setting the trends that were currently glorified by the Internet. Menswear was gaining steam at the time, but everybody was looking at was happening now, and not back then. I’m not the only one who did this, but there wasn’t really a concrete site that looked back and said “These guys did it before everybody, and they looked really fucking cool doing it.”

With Tumblr’s image-heavy format, do you think it’s easy for a lot of people to lose the context of what they’re seeing?
Oh yeah, definitely. It waters down some images that are very powerful. One thing that’s rough with Tumblr is it’s really easy for people that maybe shouldn’t have a voice to spread misinformation. That’s why my site looks the way it does. I never wanted to offer an opinion because I feel like it’s unnecessary for what I want to do. It’s just the last name and that’s it: Here’s this person, and this is who they are.

Where did the name come from?
Honestly, I was in my apartment in California on a Sunday, just messing around on the Internet and I just kind of made up the name. That’s when I started the website. It didn’t come from anywhere. I just made it up. It came from thinking that no one right now is doing it as good as those guys back then. That’s just the world it was. It’s not that people don’t have the same sense of style—the world was a different place. That’s where the “impossible” part comes from: We can’t go back to that.

Do you think it’s taken on a second meaning? After all, you’re posting photos of guys like Miles Davis and Paul Newman.
Yes, but I never wanted it to be like “you have to be an actor to be cool.” Ken Kesey and Jackson Pollock are just regular-looking dudes, but they’re just as cool to me as Paul Newman. I always wanted to convey the spirit that you don’t have to do a certain thing or make a certain amount of money to be “cool.”

If you have any sort of blinking on your site, music, annoying things like that—you are officially in the wasteland of Tumblr.

There was actually a kid who wrote a term paper on the site. He was the first one who got exactly what I was trying to say: Coolness is not a job, it’s not what you do, it’s not what you own, it’s not how much money you have. That point was very important for me to stress as the site began to get popular.

When did you notice that your Tumblr was gaining popularity?
I’m good friends with Michael Williams of A Continuous Lean. Williams gave it a shout on ACL, and I have to give him props for getting it out there. As soon as he mentioned it, it was off to the races, traffic-wise. 

Did it open up doors for you? 
It helped in a major way. Before, I'd worked with Michael on stuff for Cole Haan and did some things for Todd Selby, but I mean—I’m currently sitting on the side of the road on the PCH in California on a job for a major luxury brand. There are a hundred photographers out there, but Ghurka came to me because of my site. As much as the word “blogger” is overused and thrown around, the site definitely helped me with my career. It put me in front of a lot of people.

Do you think it gave you social leverage or credibility?
Yeah, and if someone knew I did that site, it was always easier to talk to them. I was in that menswear world a little bit, hanging out with Michael before the site came out, but as an observer. It was about a year or two before I launched the site. When it came around, people dug it, and it definitely opened doors.

What is your most reblogged post on The Impossible Cool?
It’s a Clint Eastwood picture and I think it has a little over 10,000 notes.

How many followers you have right now? 
I have 70,000 on Impossible Cool. I have 17,000 on A Conversation On Cool.

How many of the people who follow you skew into that younger demographic?
Tumblr is a younger generation. I’m 34 now. I don’t think there’s a ton of 34-year-old guys starting new Tumblrs. I noticed that youth is a huge part of Tumblr. If you go to the Popular page at any point there’s like cupcakes with sprinkles and kittens on it. I’ve always been conscious of what I’m putting out there, that coolness isn’t how handsome or hot you are—Frida Kahlo is on there as well as Jackie O. I wanted to show kids it’s not a comparison or contest.

So is Tumblr a primarily young platform? Ten years ago teenagers had LiveJournal and Xanga. Are they on Tumblr now?
Oh yeah, for sure. Now it seems to me that Tumblr is almost a standard. I would say it’s one of the first platforms that has had that status. I’ve never had a company come to me and say “Can you do a Blogspot for us?” or something like that. Kids are always the first ones to catch onto these things, and they’re always going to be the driving force behind this stuff. Youth has that sensibility to it. I think that the fact that it’s so popular with the younger generation is why Tumblr just sold for 1 billion dollars to Yahoo!

Do you think the popularity of The Impossible Cool is a testament to classic men’s style?
I feel like I can’t really answer that question. That’s sort of an ego question. I think people juust weren’t seeing these types of images. Getty wasn’t doing anything with their photos. Corbis wasn’t doing anything with their photos. When all this stuff started hitting the Internet, and people were seeing Steve McQueen looking cooler than anyone in the present day, I think that everybody woke up a little bit and went “oh wow, we need to look back on this stuff.” To me, before the Internet blew up the past, everybody was looking forward. Now if you flip through the pages of any magazine, everybody’s looking back. 

Do you think it’s a good or bad thing to sort of model your style after these famous icons?
It’s definitely a good thing because fashion—and I’ll use the word “fashion” because I don’t want to say style—within the past ten years has gotten a little ridiculous. I think it’s good for people to look back and notice that simplicity at its best will always win. To have a guy say, “I don’t need a striped suit, polka dot tie, and paisley socks to stand out; I can put on a black suit, white shirt, black tie, and look cool as fuck,” is a very good thing. I think people get a little bit out of control at times in order to get noticed.

Yeah, everybody wants to be a Nick Wooster.
Exactly, and not everybody can be Nick Wooster. Nick dresses crazy, and he’s one of the only people who can pull that off. There are a lot of guys who can’t go to a store, pick out a tie, and put it together with a shirt. The way these guys were dressing back in the ‘60s was an easy way to dress. They didn’t have crazy patterns, but they were making statements.

If you look at a picture of Mick Jagger, he looks cool in anything he has on. I remember this photo of him in a suit that was pretty ill fitting, but Mick still carried it very, very well. Any guy can look at that and see that it’s more about how you conduct yourself and put everything together, than about having the latest Junya Watanabe shirt.


In 2010 you started a second Tumblr, A Conversation on Cool. What led up to that?
I wanted to create an environment that people would constantly start sending me stuff, to the point where it became a place for anybody to post. I was getting a lot of suggestions for people to put on the site, and people were sending me their family members, like dads in the 1940s in front of their Chevys. I always thought that stuff was rad, but it just felt too personal for The Impossible Cool.  If you read the first post, I go into what I wanted to happen with the site, but it never really caught on. So it just turned into stuff that caught my eye but didn’t fit on The Impossible Cool. I’m a lot looser with it.

What do you make the proliferation of quote posts? I know that’s something you do a lot.
People love the quotes stuff, man. When I first started putting quotes up on my website, they were quotes that had to do with style. Actually, one of the things I liked back in the day that influenced the quotes was Walker Lamond’s 1001 Rules For My Unborn Son. I always thought that site was pretty cool, and the way he was portraying this person speaking to someone in the future was interesting, so the style quotes came about from that. You’re looking at images of these people, taking notes from their style, and now you get to see how they think as well. And then I ran out of style quotes, so it turned into quotes about living a good life.

Honestly, one of the worst things to do right now is start a new blog.

What’s your favorite photo on The Impossible Cool?
My personal favorite is actually the photo that started the site, which is Serge Gainsbourg with Jane Birkin wrapped around his leg. That was it. I was like: “Damn. This guy is the coolest motherfucker in the world: He’s got Jane Birkin wrapped around him and he looks like a crazy Frenchman."

How did you encounter that photo and why does it mean so much to you?
That was one of the photos on the Paul Smith board. When Clyde put it up, I was like “Man that is a pretty unbelievable photo.” I wanted to be that. I wanted to be Serge. Every guy wants a Jane Birkin. Every guy wants to look in a pinstriped suit... But I actually like them all.

You like them all?
I do, every single photo on that site I like for some different reason. Whether it’s from a photographic standpoint or what if it’s about a really nice photo, or just the person that’s in it, or what’s being said in it.

What would be your dream photo to stumble upon?
I’m a sucker for The Rolling Stones. Finding some rare Stones stuff would be cool, like Dominique Tarlé’s photos with them from the Villa Nellcôte when they were recording Exile on Main St. I would love to see some photos that had never been seen from that day. That was the best point of The Rolling Stones.

Who do you think dresses better now, old school jazz musicians or modern day rappers?
It’s not even a contest! They’re in the nosebleeds and these guys are down on the field. Any photo of T. Monk—that guy exudes coolness. The old jazz guys are the best who have ever done it, and some of the old blues guys too.

Who from the blues guys, Muddy Waters?
I’ve always been fascinated with the way Lightnin’ Hopkins dressed. Muddy Waters was cool looking, but he didn’t really dress all that great.

What about Ray Charles?
Ray is up there. Buddy Guy too. If you watch a YouTube video of Buddy Guy playing, you will see style personified. That guy had just unbelievable style. There’s a picture on A Conversation On Cool with him and Big Mama Thornton when he was playing with her and her band. It’s kind of like Street Etiquette, circa 1964.

Do you think those guys are carrying that torch?
Oh yeah, I love the Street Etiquette guys. I’ve always had such high respect for Josh and Trav. They’re just really nice guys and they’ve been in constant motion since they started doing this stuff. Every time I check in to see what those guys are up to they’ve always evolved in some way. Whether it’s their style or their online presence, they’re just doing it and doing it well.


Your site's popularity led to an ongoing collection of physical photographs with Sonic Editions. How’d that happen?
I met the founder Russell Blackmore via e-mail three years ago. He had this interesting collection of prints. We laughed about it because a lot of them had been on the site. I had researched doing this sort of thing on my own, but it just became a nightmare with licensing, and it was going to cost a pretty good amount of money. Russell used to work for Getty so he had contacts there, he already had framers, and he was in the UK—which gave us a worldwide reach. He came to me as a way to enter the US market, and we decided to go ahead and do a collection. Now we’re on our fifth. 

A lot of people don’t understand on why the photos are so expensive. What are they paying for?
When people are spending $300-$500 on a print, that’s a lot. If somebody’s spending that much money with you, you want to give him or her something more. You don’t just hand over a piece of paper or a frame. There has to be something that distinguishes it. These are archival quality C-prints. The next step above is an actual print. The best seller we have is one of Paul Newman walking on the beach. If you were to go somewhere like Morrison Hotel Gallery and buy that print, that’s going to cost you thousands—and it’s from the same negative we’re using!

The days of somebody gaining notoriety from a well-done Tumblr are over.

It costs money to print, it costs money to license, but you’re getting something that lasts a really long time for a third of the price. We looked at it as between a gallery style print—which costs thousands of dollars—and the college kid with a poster on his dorm wall. It’s for the guy that wants to grow up from the posters, but doesn’t want to drop a lot of money.

How'd it feel to go from having these pictures on your desktop to seeing the real-life negatives?
It was pretty crazy. At Corbis, they have this Bill Gates-funded layer. You go in and there’s a 12-inch thick door, a climate-controlled room with shelves, a computer system and all that. Meanwhile Getty’s entire archive in Los Angeles is nothing but a bunch of file cabinets in a basement, but there’s this one guy that has an encyclopedic knowledge of every photograph that exists in the Getty collection. He can take any photo out from the ‘20s up to the present day and tell you who’s in it, and most likely has a story behind it. He waited until we were leaving to tell us that that his mother introduced Mick Jagger to one of his girlfriends. Very interesting guy, and super nice.

Did the Basquiat tee you made with Deer Dana last year also come as a result of the site?
Dana is a friend of mine. What she does has a similar vibe to what I do. A lot of times she draws people from the era that I’m obsessed with. We were just talking one night and decided to do a T-shirt. I had this idea in my head to keep it New York-centric and have that Downtown ’81 vibe, so the first one was Basquiat. To me, Basquiat is one of the key New York art figures that came of of that scene. He’s somebody that I admire. I figured out which picture of him we were going to use, Dana drew it, and we released them on both sites. Jay-Z actually wore it when the Barclays Center opened. That was pretty crazy. We’re doing another one soon featuring Joe Strummer. It’ll be out by the end of the month, hopefully.

That’s when he was taking the subway to his last show right? He sat next to artist Ellen Grossman?
Yeah! He’s got the Basquiat T-shirt on in that. He wore it a couple of times on the Watch The Throne tour, and I he took it to Cuba with Beyoncé, there’s a photo on her Tumblr. Having Jay-Z be a fan of something you’ve done is pretty freaking humbling.

Definitely. That’s legitimizing on a whole different level.
Yeah, he’s the King of New York, man! 

What else are you cooking up?
There’s a book coming soon with Sonic Editions. I want it to be every single picture on the website in a nicely designed coffee table book. Russell and I are self-publishing it, but we have a contractor in London. I'm taking every detail into account: We're looking at different paper stocks; we're looking at different inks; we're looking at different ways to do the cover. Since we're not dealing with a major book publisher, we have control over everything, so I want to take advantage of that and do it correctly.

What advice do you have for other creatives using Tumblr as a platform to get their work out?
Honestly, one of the worst things to do right now is start a new blog. If you’re trying to break into the whole street style scene, then you need to look a little bit forward. That’s a bad move right now.

The people who are getting noticed online are the people whose work will probably stand out anyway. Tumblr is just an outlet for them. If your work is good, you’ll stand out no matter what, but starting a blog or Tumblr with the sole purpose of getting noticed is tough. 

Has that ship sailed?
It’s final boarding call. Just because there’s just so much out there right now, and you really have to have an original voice in order to make a mark.

Do you think that’s still possible with all this oversaturation?
I do, but it has to be accompanied by other things. The days of somebody gaining notoriety from a well-done Tumblr are over. If I was going to sum out advice for people wanting to do that, it’s: You need a completely original voice.

There’s going to be a generation shift too. The generation coming up will get sick of the current one—that one kid Ian Connor is like a streetwear superstar. He’s a perfect example. I’ve only recently heard of him, but he’s part of the generation that’s going to take over everyone that’s up there now... unless those older guys step up their game and come back with something better, which is completely possible.

At what point do you think a Tumblr goes from something really well edited like The Impossible Cool to just unadulterated noise?
I think the second you add a little sparkly background to it, that’s when it definitely enters that realm. If you have any sort of blinking on your site, music, annoying things like that—you are officially in the wasteland of Tumblr.

What’s your take on the whole #menswear thing that sprung from Tumblr?
Guys needed to learn how to dress, and there had been kind of a lull since the metrosexual thing. I was really sick of seeing the college sports hats, sweatshirts, and adidas sandals walking around SoHo.  #Menswear came in the post-metrosexual years, and for a long time it was like “that guy dresses really good, he must be gay,” and when #menswear came along, it was like “that dude dresses really well and he’s got a hot chick on his arm because of it.” He dresses like a grown-up. He dresses how a guy over the age of 20 should dress.

Of course, it started companies like Carson Street Clothiers that are now making clothes that I’d like to purchase. Before, it was tough to find really good clothes. That’s why I think J. Crew is so successful—they were the first ones to evolve their line to fit the growing tastes of guys. I’m psyched to see people dressing better; it makes for a better world. 

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