Jon Winterman


Hi I'm Jon Winterman. Welcome to my blog. I'm a freelance illustrator and portrait artist. Thank you for following, liking, re-blogging, or even just noticing my work. :-)


Portraiture: Capturing Someone’s Likeness

(Warning lot’s of writing ahead)

So I’ve been wanting to talk to you all for a while now, on my thoughts about portraiture. Especially how those thoughts relate to the portrait I did of author John Green, which you can see with me in the photo. I know I look super serious, that’s because I’m trying to re-create the John Green pose. I just think I look stupid.

I should mention before I carry on, that I am not a philosopher. These are just my thoughts on the subject of portraiture. I should also mention that I am not a writer, certainly no where near as the man himself. So I apologise for my bad grammar, I shall try and explain my thoughts to the best of my abilities.

Anyone one can draw a face. Anyone can create a portrait of someone. Whether through sketching, painting, sculpting, or photography, anyone can make a portrait. However, no matter what medium you use, to create a truly great portrait depends on how well the artist has managed to capture someone’s likeness.

To best reach this goal of capturing someone’s likeness, the artist has to think about two things when looking at a person. The physical, and the psychological.

The physical is simple, how does this person look? What are the shapes of their eyes, their nose, their mouth, their hair, their head, that sort of thing. Basically what are the persons facial features? I can always tell if one of my portraits is good or not, due to whether someone can recognise who the portrait is of before I tell them.

The psychological is less simple. With this the artist has to think about the personality of the subject, and how best to portray that personality in the image. For example you wouldn’t have someone who is very happy and open, and put them in a portrait where their posed looking angry and with them arms crossed.

So why dose this matter, and how does it relate back to my John Green portrait? Because the pose and the expression that I’ve drawn of him, doesn’t match up with what I think he’s like. Look I’ve never met the guy, but from his video’s, to his book’s, and how people I know who’ve met him talk about him, he seems like a nice, friendly, happy kind of guy. 

So why didn’t I choose a happier pose and expression to draw him in? Why did I draw him so serious looking? Why did I choose to draw the image of him from the vlogbrother’s ‘Middle School Misery’ video? Because there’s a third thing a artist has to think about when making a portrait. Their own thoughts and feelings about the person their drawing.

As someone who spent most of his teens being bullied, and still thinks about that time of my life every now and again. The video from which this image is drawn from, resonated with me on a very personal level. And from a couple of the reblogs of the post I know I’m not the only one who feels this way. Also I thought that was a very personal video for John Green. It’s just one shot, no editing, he doesn’t open his mouth, it’s all voice over, he’s talking about his past and how it relates to the present. I don’t know just feels personal to me. Hey maybe I could be wrong.

Anyway I’ve rambled on enough, and my computers going to die if I carry on. I just wanted to share my thoughts and feelings. Thank you to whoever’s read all of this, and thank you to John Green for a great video and being an inspiration.

john green vlogbrothers thoughts portrait sketch sketchbook photo self portrait middle school pen art Illustration serious artist artist on tumblr

Red Card Portrait Sketch 17/08/14

John Green

I’ve been meaning to post this for a while, and I would think it rude of me to tell you about the people in the other red card portraits, and not to tell you about the awesomeness that is John Green. So here we go.

For those of you who don’t know John Green is an author and a youtuber. He has written some amazing young adult novels including, ‘Looking for Alaska’, ‘An Abundance of Katherine’s’, ‘Paper Towns’, and ‘Will Grayson, Will Grayson’, a book he co-wrote with David Levithan. His last book ‘The Fault in Our Stars’ is a New York times bestseller, and was adapted into a film which was released earlier this year. And before anyone asks me, yes both the book and the movie made me cry. John Green is also one half of the vlogbrothers channel. A video blog which he co-created in 2007 with his younger brother Hank.

To be honest I haven’t really been watching the vlogbrothers videos for long. This time last year after coming home from university, I just happened to binge watch my way through their videos. By the end of 2013 not only did I know who John and Hank Green were, I had watch all the over 1000 vlogbrothers videos. I had also watch ‘Crash Course’, ‘Sci-Show’, ‘Hank Games’, ‘Brain Scoop’, and ‘The Lizzie Bennet Diaries’. I also had Hank Green’s albums on my iTunes and I got all 5 John Green books for my birthday. I hope it’s safe to say I am a Nerdfighter.

Link to Vlogbrothers Channel:

Link to Crash Course Channel:

Link to John Green’s Tumblr:

My next post will be the last one talking about the John Green portrait. After that the next portrait is Nathan Fillion! 

john green hank green vlogbrothers the fault in our stars books portrait sketch sketchbook youtube youtuber crash course nerdfighters looking for alaska an abundance of katherines paper towns will grayson will grayson pen art Illustration illustration project jon winterman winterman artist on tumblr

Middle School Misery

"Good morning Hank it’s Tuesday. So due to tornados, and broken airplanes, and a chain of events too complicated for my exhausted brain to unravel. I have visited airports nine times in the past one hundred hours, and I am very tired. And resonantly I unexpectedly found myself, alone, on a train, in New York, the city where Brotherhood 2.0 began for me. And also the city where earlier this year we played a sold out show at Carnegie Hall, a dependant clause that I will get tired of saying, when-never. So anyway, there I was on the train blinking a lot, because my eyes desperately wanted to be closed. And I kept thinking about this Tumblr message I had received earlier from a middle school student, whose currently attending the very same school I attended in Seventh Grade, and who has one of the same teachers that I had. The message read in part:

“Miss (Name Redacted) and I were talking, and she told me that you were a quiet, unique, and miserable boy in middle school. She also told me you were bullied because of your awesomeness.”

It didn’t feel like awesomeness at the time of course. At the time I was just miserable. I mean Hank you’ll note that this teacher didn’t say I was a good student, because I wasn’t. I wasn’t merely a nerd. I was, or at least I felt like I was, a stupid nerd. Which is like the worst kind of combo. I take that back, pizza combos are the worst kind of combo’s, they are an insult to pizza.

But anyway. I almost never think about middle school now Hank, but the message really forced me to remember it. And also I was on a train, which inherently makes you kind of nostalgic. So yeah, it was true that I was miserable, and that I was bullied. And in fact I would often fantasies about hurting my bullies, or holding a gun to their heads and making them apologize, making them feel as scared and powerless as I felt. But of course that isn’t the way forward.

I realize now that the people who bullied me were not evil. They were kids living with their own fear and pain. Some of whom were dealing with trauma and abuse that I could never of even imagined. Now that doesn’t justify their behaviour, but it does help me to understand, that it really wasn’t about me. Their treatment of me was not a reflection of my value of a human being. And while it was very difficult of me to feel anything but miserable in those days, in retrospect, I survived middle school because many people were in fact quite kind to me. My parents, teachers, fellow nerds, and even popular strangers who wouldn’t stand for bullying. We decide collectively what kind of behaviour is acceptable, and while ‘The Lord of the Flies’ would have you believe that like adolescence will always descend into mere cruelty. My experience of social orders has been much more complicated. I’ve found that sometimes, often even, kids are capable of tremendous kindness and generosity. In fact that’s been the hallmark of the nerdfighter community for more than seven years now, and I’m proud to be a nerdfighter, in part because I wish so much that I could of been one in seventh grade. There are always nerdfighter’s in our pants (link in the do billy do) who will listen to you if you also listen back, and that is truly awesome!

Right, so anyway Hank, there was this moment on stage at Carnegie Hall during the sound check, when Jon Darnielle of The Mountain Goats said into the mike “This is a message for sixteen year old me. Not only did you survive, you are playing piano at Carnegie Hall”. Now I’m not going to tell you like everyone who has a tough time as a kid ends up at Carnegie Hall, but the idea that those years have to be the best of your life is ridiculous. So to the young woman who wrote me. To myself stranded far from home, in an endless string of airports and train rides, I call up the great Robert Frost quote, “The only way out is through. You will get through. I will get through”. Hank, I’ll see you. Hopefully from Indianapolis, on Friday.”

John Green

19th November 2013

Link to Video:

john green hank green vlogbrothers youtube youtuber red card project Illustration illustration project portrait sketch sketchbook pen Nerdfightaria nerd fighter dftba middle school vlog jon winterman winterman the fault in our stars looking for alaska an abundance of katherines paper towns will greyson will greyson author writer artist on tumblr

W.I.P: John Green


Usually I’d spend my time on the work in progress post talking about the challenges and difficulty’s that I found when tackling the portrait. However I’m going to be writing a long essay, on the goals of a portrait for my next post, and why that relates to this portrait in particular.

Don’t get me wrong this has been a difficult portrait to draw, and I’ve been stressed about making mistakes due to my work gaining more attention. Which inevitably has led me to make some mistakes. Also I’ve had too fight all my natural instincts as an artist, just so I can draw this image. More on that it my next blog post.

Anyway I wanted to spend sometime saying, thank you. Thank you to the just the astounding amount of people who liked, and reblogged my last portrait. I never thought I’d see one of my portraits get over a 1000 notes on tumblr. Thank you to all my old and new followers. Thanks to you I finally have over a 100 followers. And finally a big thank you to Grace Helbig and Hank Green for liking and showing people my work. You guys are awesome all awesome!

Speaking of awesome, next portrait is that of John Green. I am going on a little vacation tomorrow, to the Isle of White, to meet up with some friends I haven’t seen in a very long time. However I promise the final portrait will be up on Monday. And then after that Nathan Fillion.

john green work in progress WIP Illustration red card project illustration project Portrait Project portrait vlogbrothers hank green grace helbig dftba nerd fighter sketch sketchbook pen winterman jon winterman artist on tumblr