HUMOR

A Year of Learning to Draw

A collection of my drawings as a noob on a Microsoft Surface tablet

It all started when I quit my job to travel around. My present to myself was a fancy new Microsoft Surface tablet.

Why did I choose to get a tablet, of all things?

1. I wanted a convenient tablet to carry around for my travels
2. I had always wanted to learn how to draw

So, in my travels throughout the following months, I finally took some time to learn how to draw.

Not well, per se, but drawing nonetheless.

Here’s a collection of most of my drawings over the past year. I’ve sorted them by time, so you can kind of see some improvement in certain areas.

*Note, for some reason some of these images below upload into Medium much wider than the originals — my apologies.

J.J. Pryor’s Paintings

Before I quit my job, I tried my hand at painting for the first time in my life.

I wasn’t very successful.

Here are a few of those (unfortunately I misplaced the actual drawings in my travels).

Here’s a brutalization of a good buddy’s portrait. This got a lot of laughs — fortunately.

Another unfortunate volunteer for my newfound hobby. I genuinely felt bad showing her this result.

An attempt at a peaceful monk sitting and meditating. I don’t think he’d be at peace after seeing this, though.

J.J. Pryor’s Drawings

At this point, I set off on my travels with my new tablet in hand.

No more painting and cleanup for this guy.

Here’s my first attempt at a portrait on the tablet. You could definitely see I had my work cut out for me.

I drew this while chilling out at a beautiful cliff-side in Bali. An extremely serene and beautiful place and a perfect place to start learning a new hobby.

And the view for those interested:

It’s at this point that I started incorporating photographs and tracing into my drawings. I also began to play around with some of the textures.

You can start to see some improvement on the next portrait.

That weird blue thing at the bottom — my attempt at drawing smoke.

Around this time is when I made my 2nd attempt at a personal portrait.

Yikes.

But I was starting to learn aspects of shading. Here’s another friend that volunteered at this point.

I liked the idea of incorporating real images together with the cartoonish style. Here was my first attempt at that.

Note, my friend requested this photo — and I was probably a bit too generous with the shading — to his enjoyment.

And one last one that I was quite happy with, but took a very long time to create.

I didn’t draw for a while after this as life and travels got in the way — as they tend to do.

I returned to it with a funny concept a friend and I came up with — political cat cartoons.

AKA — The PolitiCat Party

J.J. Pryor’s Cartoons

The premise was simple enough, if not weird.

Cats as politicians. Heavy on the puns.

My only problem was I had no idea how to draw cartoons. As you can see with my first attempt. (Forgive the handwriting.)

The Communist Cat Party

This was quickly followed up with another one along the communist theme.

Joseph Pawin

Enjoying the pun more than the drawing, I spurred on.

Next up, USA.

John F. Kattedy

Slightly better but still a lot of work. I knew who the next target had to be.

Donny Trump

After this, my friend asked me to draw him a very specific diorama (is that the right word?) for one of his novellas. I liked the results of this one.

After this, I stuck with the politicats theme and cranked out a few more in the coming months.

Obameow

And another take on a classically infamous phrase:

Don’t worry, I love dogs. I just thought this fit the theme well.

Then I moved onto a very relevant figure at the time.

Purrnie Sanders

I even made a t-shirt out of this one, just to explore dropshipping and print-on-demand services. It was a pretty cool feeling to wear something you created.

My friend also suggested another idea for a very cat-like behavior.

Julius Catsar

I also had to make one for the former VP too. Although this joke didn't really land, it was fun trying to make.

Cat Joe Biden

I even took a shot at a popular meme combining it with ol’ Trumpy.

Tweeting on the Throne

And the last drawing that I haven’t quite finished — not really sure where I was going with this one. But it sure made me laugh.

Cleocatra — Wearing a MAGA hat for some reason

One thing I did quite enjoy, although the time spent was way too much, was creating my own header images for some of my humor articles.

Elon Musk’s To-Do List

Bill Clinton’s Stain Removal Advice

And lastly a playful reconstruction of a famous image in the news at the time.

How to build a hospital in 6 days

Wrap-up

I know these aren’t a huge amount of drawings (I think I misplaced 5 or 6 more), but it was a fun process learning to draw these.

I now know the extreme amount of patience, practice, and proficiency required to be a good artist.

It’s taught me 2 things:

1. It takes me a long time to draw
2. I have huge respect for real artists

And I’m not sure I have the effort in me to continue because of the time factor. I haven’t drawn anything in a few months now, but keep thinking about it.

That’s why you see this collection in front of you.

I’d love to hear any feedback from other artists and readers out there. Which styles did you like? Any advice? Should I keep drawing one of the styles or call it quits?

Anyway, if you’re still with me, thanks for looking at my attempts learning to draw this last year!

Until next time, have a good one.

Keep up with my guides, rants, deep dives, and crazy shenanigans with my free newsletter. Thanks and have a great day!

J.J. Pryor