My Favorite Digital Drawing Tools
This post is long overdue, especially considering I work mostly with digital painting. You can find the counterpart to this post, My Favorite Analog Drawing Tools, right here.
I've tried so many drawing apps and tools, and these are winners. The TL;DR answer is that I love the iPad Pro, Apple Pencil 2, and Procreate. I know that feels like a big up-front investment, but if you are planning to really commit to digital painting it's all you really need. 
Read on for a more detailed assessment, updated as of January 2020. A lot has changed since 2018!

Some of my favorite things

Hardware & Accessories
1. Best Combination: iPad Pro and Apple Pencil (2nd Generation)
It feels really natural to draw on the iPad Pro with the Apple Pencil. I'm not an Apple fangirl so I am completely unbiased in this assessment. Try it in an Apple Store first, as it is a big investment. I think the smaller iPad sizes work fine if you're just starting out or doing simple drawing, but for me I really love the 12.9" Pro version. As for the other specs, get what you need. I personally do not need data, and I don't do much on the iPad other than draw and write, so the Wifi 256GB is perfect for me. 
You really do need to use the iPad Pro with the Apple Pencil to get all the benefits—I used to have a bunch of styluses ranging from Fifty Three's Pencil to Adonit's Jot Pro, but they pale in comparison to the Pencil (I feel like Apple purposefully makes it hard for theirs to compete). And the latest generation is a significant improvement over the first, so I'd recommend that upgrade.
Finally, I do recommend the Apple Smart Keyboard Cover and a paper-feel protector to complete the kit. 
J also has the Microsoft Surface Tablet and it doesn't compare in terms of pressure sensitivity which is so important for drawing.

2. Best laptop: Macbook Pro
If you are not illustrating for a profession you really just need the iPad Pro and Pencil. Actually many professionals are migrating completely to the iPad Pro. And that's amazing for being able to work from anywhere. For me, I still need to do final work on the computer because there are still some capabilities that the iPad Pro doesn't do as well in terms of the final file preparation. I need to use the Adobe suite on my computer for that. 
I do still think Apple's line of computers work best for creatives. I actually don't really like Apple's approach to business so I tried to migrate back over to a PC, but Microsoft still hasn't caught up for my UI/UX priorities. Just my opinion, but most creatives do use Apple for a reason, at least for the time being. I used my first Retina 15" Macbook Pro for five years before purchasing my latest Macbook Pro in late 2018.
I also like this dongle because there are not enough ports on the Macbook Pro.
Bonus Tip: The latest iOS has a feature called Sidecar for the Macbook Pro. It turns your iPad into a second screen for your Mac, and it works really well! It effectively makes your iPad a Cintiq too. 

3. Non-Screen Tablets: Wacom Intuos Pro
Many people already have a computer and do not have the budget to buy an iPad Pro right away. That was my situation when I started as well! 
Enter the Wacom tablets. They dominate in this field. I used to use the Wacom Intuos Pro for a long time and I still would recommend it if you need a tablet. One benefit vs. working on a screen tablet is that you look forward at the screen instead of straining your neck down. I honestly find the small and medium sizes work about the same for me (I have one at work and one at home), but medium does feel a little more free if you have the budget for it.

A Note About Wacom Mobile Studio Pro  and Cintiqs
It used to been a dream of mine to own a Wacom Cintiq. When I finally saved up enough a few years ago, I got a Wacom Mobile Studio Pro and I was so excited. It's a laptop and screen tablet in one. I thought it would be the answer to everything. 
I tried to love it, but it just didn't work out. Wacom makes great tablets but not very good computers. I personally concluded it's best to stick to a dedicated computer and a dedicated drawing tablet. 
Later in 2019, I used a Wacom Cintiq Pro 22 while working for my client. It's really nice! Amazing if you can afford it. However, if you do not have the budget for it, I think the iPad Pro is more than enough. Do not even worry about it. I often find myself drawing on the iPad instead of the Cintiq since it's just easier and quicker in some ways. And, Cintiqs are obviously just not transportable. So unless you are doing intense professional artwork, it's just not necessary.

A Note For Beginners
If you look at these products, you'll probably be a bit sticker shocked. I sure was when I started looking into them more seriously. Even the iPad is a luxury! If you're just starting out with digital drawing, I would recommend getting a cheaper Wacom tablet and use your computer with the $10/month Adobe Photoshop Creative Cloud plan. See if you like it before you commit to anything more expensive.
I started out with a Wacom Bamboo, which they've discontinued and now the equivalent is this Wacom tablet. It's totally more than enough for a beginner!
Apps & Programs
1. Best Digital Painting App: ProcreateI absolutely love Procreate. It is worth way more than the $10 the developers charge. Buy it today if you have the iPad. It's so powerful and they keep improving it. I love drawing with it, and do most of my sketching and initial design work with it. Sometimes I even finish it in Procreate. It's way better than Adobe's iPad drawing apps, even with their recently released Fresco and Photoshop iPad apps. 

2. Best Digital Painting Program: Adobe Photoshop
Procreate is amazing and you probably don't need more than that if you are a hobbyist. For more complicated digital painting and design work, I still need Adobe Photoshop. It's still way better for illustrations mixed with graphic design and photo editing. It's very powerful.
While I was annoyed with the subscription model of Creative Cloud at first, it's really grown on me. Since it's now my work, I think Creative Cloud is totally worth the $50/month for the full suite. There's a lot of interlinking that is quite helpful.

3. Best Designing and Storyboarding App: Concepts
Designing and storyboarding are a bit different than sketching and digital painting, even though both involve me drawing. For the former, I like using this app called Concepts. I like how natural it feels to draw, but all the lines are vector so it's easy to move things around when designing. It also features an unlimited canvas which is great for the way I storyboard.
Side note: I used Concepts for a long time before they reached out to me after seeing a post I tagged them in. I subsequently worked on an illustration for them as well as writing an article for them, all about storyboarding. Check it out here.

A Note About Astropad
There's an app for the iPad called Astropad that allows you to connect your iPad to your computer and use it kind of like a Cintiq. Some people really like it. I don't like that the Pro version is a subscription model, given that it still has some lag issues for me. It never replcaed my Wacom, even after I tried the subscription model.
As of 2020, if you have a Macbook running on the latest iOS, the Sidecar feature mentioned above renders this app useless for me. However, if you do not have a Macbook, it can still be useful to pair your iPad so I'm keeping it here.
Last Notes
Is the investment worth it? If you are taking digital painting seriously, this by all means yes. Start with what you have and the best tablet you can afford—the $50 one is fine! Then start saving as much as you can and upgrade your tools one by one if you are on a budget. And, as always, never let not having the perfect tool prevent you from just getting started. 
I hope that was helpful!
This post was originally published on on March 11, 2018 with updates on January 5, 2020.

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