
EDITOR’S NOTE: Last October Sydney Smith flagged down the Bus. Later that week his book, Sidewalk Flowers, won the Governor’s General Award in Canada. It was also named a New York Times Best Illustrated Book. Not bad!
Conversation started 27 October 2015, 9:44 p.m.
SYDNEY: Hello,
It was a while ago, but in San Fransisco we were introduced by our mutual agent, Emily, and i wanted to reach out and say hi, from fan.
I hope you are having a good autumn!
PHIL: Hey Sydney!
Man, I’m glad you wrote when you did because now I can say we were pals from before you got HUGE. You’re blowing up this week! Seriously, congratulations on all the good news this week. Honestly, I knew you were a shoe-in for the NY Times list from the first time I saw the book. But it’s easy to say that as an outsider, and much different when you’re actually the guy who made the book. Not that many people can REALLY draw like you can. It is so incredibly refreshing to see a book like Sidewalk Flowers get a nod.
So what are you working on now?
Sidenote: I was checking out the art on your website and I was suddenly reminded of one of my favorite artists that I haven’t thought about in a long time—Ben Shahn. Your work is not exactly like his, but it feels like a close cousin.
SYDNEY: Phil,
thanks for writing back! Yeah, yesterday was pretty crazy. Two bombs landed and i’m still feeling pretty rocked. The NYT list was something i didn’t even want to hope for out loud and now its been released the same day as the Gov. Gen. Awards… which is pretty big for this little Canadian. I get a few trips out of it but i’m sure its back to work before long. Honestly ill be glad.. .its a bit distracting and i work better when i don’t have the pressure.
Thanks for the kind words. After doing Sidewalk flowers i’ve been flopping around trying different things. and Groundwood’s been nice enough to let me try different things out. theres been a couple books since but nothing like Sidewalk Flowers. Partly me, but partly the manuscripts. for the past year i’ve gone and booked myself with practically anyone who makes eye contact but all i want to do now is polish up some stories of my own and fly solo. Writing, it turns out, is harder than drawing.
Ben Shahn! yes! i just read “The Shape of Content”. I thought it was pretty damn good. I read it a lot on the street car. He’s definitely one of my favourites.
right now im illustrating Canadian History for a book about the last 150 years of Canada.
Im illustrating a chapter book for Susan Rich and Esta Spalding called Look out for the Fitzgerald Trouts.
then theres another picture book for Groundwood about growing up in a Mining town in Cape Breton, Nova Scotia. That hits home. almost literally. and think thats gonna be where i pull out the stops.
Congratulations on Lenny and Lucy! its such an amazing book. Years ago i used your books when teaching about making children’s books in a night class at my local University. Its great to connect with you.
your pal,
Syd
PHIL: I should find that Shahn book. I didn’t know he did a Norton lecture. A couple months ago I read William Kentridge’s Norton series called Six Drawing Lessons. It was extremely dense, sometimes irritatingly so. But I love the guy so I stuck with it.
I’d love to see some work from the mining town book once it’s going (and if you’re inclined to share). Do you know the Groundwood book, I Know Here? It’s one of my favorite picture book texts ever. I go back to it all the time. It might not be anything like your book, but your description made me think of it.
SYDNEY: I just ordered the Kentridge book. I don’t mind density usually, if its something i’m passionate about. And that might be the one thing I’m passionate about. That and doing donuts and hot doggin in my low ridin’ honda civic. and kicking sand in nerds faces. and stealing their girls.
I do know I Know Here, its a great book and i hang with Matt James, its illustrator here in Toronto. We get together, talk shop and drink tasty local beers into the early hours.
My wife teaches ECE so i get a lot of inspiring and insightful thoughts from her but it when it comes to the industry theres not many people to talk to. A lot of people i know still think its about drawing kittens who have lost their mittens. not that theres anything wrong with that, its just not my bag.
The mining town book will be pretty special for me. I hope i can stay true to my vision for that. usually what happens is i set a bar and imagine something that takes a lot risks and pushes my own boundaries and comfort zones but usually i fall short and play it safe at the last moment. then i get really disappointed with myself. and go on a bender.
is there any other good writing on art or writing out there that makes your bull run? Ive been looking at so many photos and watching so many beautifully shot movies lately that offer some great inspiration. Ive been watching a film history series on American Netflix, i guess just Netflix to you. Canadian Bacon is not just bacon to me. thats just fried ham. Any way, the narrators voice in the show is hard to listen at first but its fantastic.
What are you working on? anything exciting?
PHIL: Hey There,
Sorry for the, um, three month delay in writing back. We left for China the day you last wrote. And then, when we got back a few weeks later, people in our life just kept dying. For real. We went to 4 funerals in about 6 weeks. That kind of horror has a way of messing with your life and email flow.
Sheesh.
But anyway, look what I found!…

I ordered it from a bookstore in Ann Arbor weeks ago and it finally arrived. Thanks for the tip.
As for my own recommendations for dense art theory reading, I’m not sure I’ve got any good ones. I remember being really blown away by Dave Hickey’s Air Guitar, Essays on Art and Democracy. I read it in high school though and I’m not sure if it would still blow my mind in the same way. I should dig it up and see if its still got anything to offer. There are some George Saunders essays on art and writing that I particularly love. Most notably the one about Kurt Vonnegut that’s included in The Braindead Megaphone.
Would you like to see some pictures from China? Of course you would.

Here’s Tiananmen Square.
Here’s Mao.
Here’s our translator, Jenny.
Here’s a smoggy day at the Great Wall.

And here’s our translator, Jenny, again. This is maybe my favorite photo I’ve ever taken.
It’s funny, everyone in the world has a camera in their pocket now, but if you pull out a Polaroid camera people flock to witness its black magic. I think camera phones have made images totally meaningless.
It’s weird that you sent the hedgehog video. I’d never heard of it until just recently when our friend, Jon, said that Erin’s new book reminded him of that film. Here’s a peak at proofs from Erin’s book. It’s my favorite book she’s made.
And while we’re at it here’s what I’ve been working on this week.
And you?
SYDNEY: Hello!
I’m so sorry to hear about your many losses. I know how that feels. insane and absurd when it happens all at once.
The photos from your trip are beautiful and i love that they are polaroids. Ive been thinking of getting a camera. I love taking photos but i don’t have decent camera. My wife and i are expecting a baby in July and i think i will want one. I have no idea what to expect, though. Im a child about to raise a child. I’d love to visit China. I work in Chinatown in Toronto and there are more mandarin spoken here than english. its great.
I’m glad you found that Ben Shahn book. i loved reading it. I got the William Kentridge book, Its a beautiful book. Im excited to read more of it.
Erin’s sketches are beautiful. Is her book written by her as well? My wife and i both love horses, especially my wife. we both were around horses growing up.
And Samson in the Snow looks fantastic too. When does that come out?
Im writing my first story right now and its set in winter. Ive been refusing manuscripts from other people (which i’m sure emily loves) and although i’m still committed to three more books I look forward to the new life of writing and illustrating for myself. but lets be honest. I haven’t proven to anyone i know how to write yet.
Maggie and I are going to Italy in March for one last trip before there are three of us. I thought i could see what the Bologna book fair is like. I’ve been told that its pretty inspiring. Before that we are going to be staying in Rome for Easter. check out el papa.
The book i’m working on right now is set in cape breton. in the 70s. Its a day in the life of a boy whose father is a miner. In the background it will show a contrast between the beautiful landscape and the struggle in the community. Slightly gritty, unglamorous but still beautiful. But that is the maritimes. I hope it works out. ive been thinking about it for a while and its important i do it right considering i’m from there.
My last book, the White Cat and the Monk, is getting some good reviews but it hasn’t got the same buzz as Sidewalk Flowers. i guess i’m still learning about this business but maybe the first thing i need to learn is not to read reviews or worry about accolades.
I’m just finishing a project with a children’s ward at a local hospital. Ive been making murals for it for the past 2 years. It’s done. im wrapping up so much stuff right now. alot of projects that have been going for the past 2 years are ending tomorrow.
Im at the studio right now. I should head home and see if how maggies feeling. Thanks for keeping in touch.
PHIL: Yo,
Definitely get a camera. I love my Polaroid cameras. I have three right now, although film for one is hard enough to find that it’s become more of a paperweight. My pictures from China were taken with
this guy.
I guess technically this is a Fuji camera not a Polaroid, but Polaroid is more of a concept than a brand in my opinion. I think a while back Fuji bought Polaroid’s camera technology and started using their own film in the new machines. Fuji’s film is colder and bluer in my opinion than Polaroid’s used to be. It frustrated me for a few years, but I’ve made my peace with it. I just like that film cameras have limitations that force you to think before taking a shot. A film pack costs about 10 bucks and it has 10 photos, so every photo costs a dollar. There’d be a lot fewer soft focus online photos of people’s farm-to-table brunches if each shot cost a dollar. I’ve run the numbers and I end up getting 2.5 good shots out of a pack of 10. The rest are throwaways. But at the end of a year I have 20 or 30 real photos that actually represent my life as opposed to the thousands of not-real photos that only exist in ones and zeroes on a Cloud somewhere. I’ve had a thing for crappy cameras for a long time. Their results always seem more accurate to my memory of a situation. There’s something spiritually correct about the incorrectness of a Polaroid, or of any camera that struggles to get the details quite right. My senior thesis in college was a black and white photo essay on architecture in Detroit. For four years in photo class I’d been taught to take as many photos as possible on the assumption that quantity precludes quality. That always felt wrong to me though, so for my thesis I bought a half broken medium format Yashika camera from the early sixties, fixed it up, loaded it with a single roll of 12, and spent three months taking those 12 shots. I think 11 of the 12 ended up in my show. I’ve got them in a closet somewhere. Hang on…
Hmmmm. Can’t find ’em. They’re around though. Maybe some other time. I did find these other photos I took in Detroit when I was in high school though, circa 1997.
Anyway, all that is to say, if you buy a cheap camera you won’t regret it.
Erin did not write the horse book. Erin has yet to write her own text. It’s a weird story of how we ended up with that text though. We were in Nashville a few years back for a book festival. After our event we were waiting for lunch and I bought one of those street newspapers that are distributed by the homeless population. There was a poetry feature in the paper and this one poem about a milk cart horse stopped me dead in my tracks. Several months passed and (long-story-short) we convinced Macmillan to track down the rights to that poem. Unfortunately the author of the poem, a man named Ed Galing, had died just two weeks before we went looking for him. He was 96 years old. So next year Ed’s first picture book will come out, pretty damn close to what would’ve been his 100th birthday.
Samson in the Snow comes out in October (I think). I have no interesting origin story for that one.
Hey, how’d you make this image?

Ink and what? I’d love to make a black and white book someday.
Congratulations on the kid! That’s very exciting/terrifying. People ask us all the time when we’re going to have kids. Besides the fact that it’s totally invasive I always think, who the hell am I to have a child? I have a hard enough time waking up before noon already. I am a child. Still, other people seem to figure it out.
Definitely stop reading reviews. Nothing good can come from it.
SYDNEY: Hey there,
its been a while. How have you been??
i’ve been travelling around everywhere.
i decided i wanted to research the story i’m working on even though i’m fairly familiar with the setting. so i jumped on a plane and went headed for Cape breton.
It was the best decision. not only because it gave me great material for the book but i also got a little solo adventure out of it. I rented a car and drove into the island listening to the same ten pop songs on repeat because i forgot to update my phone with music.


it was freezing but i stopped by a Mark’s Work Warehouse and picked up some extra winter gear. which helped me blend in a little because leather jackets and skinny jeans would be a bit too fancy for some of the good old boys in the Tim Hortons. I got a chance to talk to some folks about mining and the mining museum allowed me to visit their building and their replication of a mine despite being closed for the winter.
After i returned i got ready for Italy. Maggie and i decided to just do it and not worry about how much its going to cost and how much time it will eat up. and though it did both of those things the trip was pretty magical. and i got a chance to see what the bologna Fair was all about. turns out its kids books. they love kids books.

thats a pretty amazing origin story for the horse book. wow.
what else have you been working on?
Im trying to write a story set in snow. called the snow fort. its been the monkey on my back for the past year. and Emily keeps asking me about it.
On the last night we were in Ravenna we went to an Opera and the theatre was so enchanting i have decided i need to write a story about it.
The drawing you asked about was done with ink and guache. it looks a little like toothpaste but i like it. i’m pushing myself to use different materials and textures. I gotta keep experimenting and changing it up or i get bored.
i just went on a book ordering frenzy. everyday theres another package arriving. its a bit embarrassing but now that there’s a baby coming i have more reason!

i gotta grab a bite before polishing off this draft of the book and sending it to my editor. I hope you are well, talk soon!
SS
PHIL: Yo!
I love that house picture. I imagine a very polite Canadian divorce where husband and wife agree to split everything 50/50.
I also really love that ink and toothpaste drawing. Kind of reminds me of this book. Do you know it?
Images like this one seem very much in your wheelhouse:

I’m jealous of your trip to Italy. I actually went to Ravenna when I was 16 years old. A high school art history trip. I remember being really impressed by the Byzantine mosaics there. I think it was my first real experience with something that old. Anyway, it left a positive mark on the psyche.
As far as what I’m working on right now, the answer is not much. Our life has been consumed for the last several months with a big renovation project. We’re converting an old barn behind our house into an art studio. The project was supposed to be done by New Year, but 4 months later it’s still ongoing. During the first 6 months of the renovation we were working together in a spare bedroom in the house. After making three books in that tiny space though neither of us can stomach being in there anymore.
Here’s the barn in winter:
Thankfully we got the okay to start moving our things in this week. So even though there’re still some things to finish we can start working again. Maybe next week I’ll feel like a bookmaker again.
PHIL: Gmail just freaked out on me before I was done with that last email. Anyway, here are some pictures of the almost finished studio.
Hey, I have a question for you. Erin and I have website where we post long conversation between artists:
numberfivebus.com
What would you say to making an episode out of the entire thread of our email conversation going back 6 months? I’ve been waiting for REDACTED to deliver three episodes he’s been working on with REDACTED, REDACTED, and REDACTED. Anyway, he’s taking his sweet time and I’d really like to post something soon. Looking back we covered a lot of good stuff. I can clean up typos and whatnot. Or not. I kind of prefer doing nothing. Whaddya say?
SYDNEY: Thank you for showing me pictures of your studio. heres a picture of mine. Carefully placed chaos peppered with garbage.

I am jealous of your studio in the country. Recently i was in an author’s kitchen for an afternoon party. He’s been widely published for more than twenty years and i told him my apartment is the size of his kitchen.
I don’t know why i would say that. I don’t compare. I am happy, and i don’t need anything that i don’t have.
I must admit i have often described my dream to my wife late at night in bed. it involves a barn studio separate to a house. with a wood stove. and a hammock.
I do like those drawings by Leonard Baskin. ill keep an eye out for that book, i feel like i’ve seen it before. Im still working on the same picture books as before. the Cape Breton book is on the top of the pile and i’m trying to stay loose. A lot of times i just go back to my sketches and try to use them after failing to create anything worth keeping.
Italy was a crazy indulgence that I doubt we will have a chance to do again.
Although i found out that i may be invited to Ireland in September. So perhaps the high living and jet-setting may continue a little longer *polishes monocle*.
I will have a new born son at that time. That thought blows my mind a few times a day. *monocle falls into mint julip*
I am not ready. But maybe when i accept that i will not be ready, that will be when i’m ready. very Yoda.
I haven’t looked at our older emails but if you wish to share them you may. Typos and all. I definitely sound more confident than i am sometimes. That shouldn’t hurt.
I am working on some books of my own and it feels scary but the right thing to do. If i can put something together and get some stories contracted up i would take my wife and baby somewhere warm for the winter. I can work and then can relax. another dream.
Do you think there is a head shop out there called Pipe Dreams?
Do you think there is a brunch menu out there that offers Breakfast of Champignons?
I do.
its my birthday tomorrow.
next time you hear from me it will be 36 year old Syd.
35 year old Syd will clock out and probably find a stable job in online marketing, start a family of his own. buy a canoe. find jesus.
i should get back to work
s
PHIL: Oh man. I hate to even tell you this, but we’ve got a woodstove and a hammock here. You might want to consider moving to Northern Michigan. Things are cheap here. And if you squint it’s almost like Canada. Our neighbor makes maple syrup.
There’s a Pipe Dreams Head Shop in Milwaukee. Not sure if they’ve got a brunch menu.
People are always finding Jesus which makes me wonder if he even wants to be found. I suspect not.
Happy birthday! And congratulations on the new gig in online marketing. Maybe someday I’ll grow up, have a kid, buy a canoe. But I’ve got 14 months till I turn 36.
If you’re ever out of ideas let me know. I’ve got a middle grade novel (not really a novel, but I don’t know what to call it) that I think you’d be good for.
Please send pictures of Cape Breton art. By the way, did I tell you we bought White Cat and the Monk? We picked it up while we were touring in Mississippi. Great book. One of our two favorites this year so far. The other being Bunny Dreams by Peter McCarty.
Our escort in Mississippi open-carried a 9mm handgun to our bookstore reading. U.S.A.!
Erin says hi. She’s making cookies.
Ok, anything after this sentence won’t be published on Number Five Bus—stay in touch though.
Conversation ended 9 May 2016, 12:45 p.m.
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