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.