List of Art challenges every artist should join!

Check out this List of art challenges and their brief descriptions.

I gathered this list of fun challenges, that not only will help you deal with your art block but will also help you improve your drawing skills. Check them out!

Important info: Originally, this was an article where I aimed to list every existing art challenge. It turns out there are a lot of monthly art challenges, so I decided to create another list, where I divided the challenges according to the months they take place:
For a full list of Monthly Art Challenges please go to this article Monthly Art Challenges [ULTIMATE LIST]

I left this article with the intention to mention here mainly non-monthly art challenges, + only the most popular monthly art challenges.

Also, for more pieces of information please visit the “Art challenges” category.

Art Challenges Quick List:

  1. ArtVsArtist
  2. Draw This Again
  3. Inktober
  4. Left Hand
  5. Different Art Styles
  6. 20 Art Styles
  7. 100 Heads Challenge
  8. Face Your Art
  9. MerMay
  10. Character Design Challenge
  11. ToonMe
  12. Magical March
  13. Six Fanarts
  14. Draw This In Your Style
  15. Sailor Moon Redraw
  16. Smaugust
  17. *Monthly Art Challenges

1. #ArtVsArtist

Briefly, ArtVsArtist is a collage compound from 8 artworks and one photo – the artist’s photo, which is usually placed in the middle, surrounded by 8 squares with artist’s works. This project is quite popular on social media – Facebook, Tumblr, Twitter, Instagram, and DeviantArt. The purpose of it is to reveal artist’s face – since many artists use social media only to post their artworks, it’s a great way to introduce yourself to your followers.

The history of this challenge, examples and a #ArtVsArtist template you can find here: link

2. Draw this again

This is my favorite challenge! And a perfect way to check how much you have improved. In this challenge, you pick one of your old artworks and draw it again – of course, implementing everything you have learned so far. It’s hard to see a progress comparing few artworks drew in a close amount of time. After a year (or even few months) of drawing, you will be able to see your mistakes and know how to fix them.
Redrawing your artwork will show you how much you have improved, and keep you motivated (well, what’s a bigger motivator than seeing a huge progress?

Author: Chemical-Exorcist


3. Inktober

Art by Maciej Kuciara

Probably many of you scrolling through Facebook drawing groups or your favorite artist’s Instagram can see drawings with unusual topics marked with a hashtag #inktober.

“Inktober” is a combination of the word “INK” and the end of the month October. Every October, artists all over the world take on the Inktober drawing challenge by doing one ink drawing a day the entire month.
The official website, created by Jake Parker, every year on October gives a list of topics that should be accomplished day after day. Inktober is about growing and improving and forming positive habits, so the more you’re consistent the better.

Learn more about Inktober here: What Is Inktober?


4. Left hand

The “left hand” challengers have a seemingly easy task to fulfill. You have to use your non-dominant hand to create an artwork. Usually, they draw the artwork with their dominant hand first, and then try to copy it with their other hand – this way is easy to compare how well you can control your non-dominant hand.
Remember, that drawing is not only about how well you can control your hand, but mostly about your imagination and the knowledge of proportions, light, etc.  By the way, have you tried this challenge in the past, and your drawing was unexpectedly good? Congratulations, you might be ambidextrous! Only about one percent of people are naturally ambidextrous.

Art by Daria Victorova



5. Different Art Style challenge

#stylechallenge was started by a 17-year-old Instagrammer called beautifulness87. The idea is simple: draw the same character multiple times in the styles of as many popular cartoons as possible. The results are pretty awesome.
It’s also a fun exercise that will help you to deal with an art block! On the internet, you can find many sheets which you can use – or create your own sheet! Here you can read more about this challenge and download a Different Art Style challenge template (PSD file)

6. 20 Art Styles Challenge

20 Art styles challenge is an art challenge where your task is to draw the same character/or yourself in 20 different art styles. Very similar to the challenge described above, but here we have an additional rule – the number of styles.

It’s a popular art challenge posted on Instagram and other social media with hashtags: #20stylechallenge #20styles and hashtags of the art styles they used in the challenge.

Here you can download the 20 Art Styles Challenge Template and see what styles are used: What is 20 Art Styles Challenge?




7. #100HeadsChallenge

I love drawing heads, it’s my favorite thing part to draw! Trying to show the model’s character and emotions on a paper is a challenge itself… but some people decided to go hardcore, and here’s the “Draw 100 Heads Challenge“!

So, the purpose of 100 Heads challenge is to draw 100 heads / portraits. The time limit is 10 days. It’s pretty limited, so it’s good to stick to drawing 10 heads per 1 day.
The challenge was started by Ahmed Aldoori, you can watch his taking the challenge in the video below:

Before taking the challlenge, Ahmed Aldorii created a pinterest board where he gathered about 100 photos. You can find it here.

The challenge is a good way to practice drawing faces – a similar homework get art students, but not only they have to draw a certain amount of faces, but also a certain number of hands (It wasn’t as easy as I thought it would be, the hand are perhaps the most difficult body part to draw).


8. Face Your Art Challenge

Face your Art is an art challenge, where the artist makes a collage of his artworks. The collage consists of 9 different art pieces made by the challenger – usually, that are faces of the drawn characters, cropped into squares.

The Artist draws conclusions from his paintings – mostly what they have in common and what drawing mistakes the artist makes and writes them in the artwork’s description.

The Face Your art challenge was created by an Artist named Chao. Here you can find more of her artworks:

You can learn more about this challenge here: Face Your Art Challenge



9. MerMay Challenge

MerMay in another fun challenge that starts in May and lasts till the end of this month. The goal is to draw a Mermaid every single day!  There are no restriction oh what tools you should use.

On the official site you can find a list of prompts for each day. It’s not mandatory to stick to the list, you can use them just as inspiration.

To learn more, visit an article dedicated to this challenge: What is MerMay Challenge?


10. Character Design Challenge

Character Design Challenge is an art challenge run on a Facebook Group, named obviously “Character Design Challenge!“. Every month, a new theme is announced, and artists who participate in the challenge have about 30 days to design a character based on the theme. The best designs win the challenge, and a new theme is announced on the 7th day of each month.  In this challenge you can actually win a prize!

Important rules:
– This challenge is exclusively for 2d artworks (traditional and digital).
– Only 1 design per theme
– If you have an old design that matches the current theme – it can’t participate in the contest. You can publish it, but it won’t be considered while picking up winners.

You can find all rules here: Challenge Rules

The Character Design Challenge is organized by Character Design References™ (CDR) an independent webzine dedicated to sequential, illustrative and concept art from animation, games and comics. You can visit their main website:

11. Toon Me Art Challenge

ToonMe is an art challenge, where artists create a stylized autoportrait – usually in cartoon style.
It’s based on an actual photo – the artwork is divided into half. One half is the actual photo, the other half is the illustration.

It’s a great way to introduce yourself to your followers, and show them your real face. Well, at least a part of it 🙂

The ToonMe challenge was created by illustrator René Córdova, a Marvel illustrator based in Guadalajara, Mexico. Córdova created the challenge on January 7th by sharing a selfie that was half photograph and half illustration.

Many artists followed him, and created many amazing ToonMe artworks, you can check them read more about this challenge here: What is #ToonMe art challenge?

Soon I will add brief descriptions to the Art Challenges listed below, right now you can click on titles an go to blog posts dedicated to these challenges.

12. Magical March

13. Six Fanarts

14. Draw This In Your Style

15. Sailor Moon Redraw

16. Smaugust (Dragon Drawing Challenge)


Why you should participate in the art challenges?

Because it’s fun, improves your skills, and teaches you to stick to every professional illustrator’s routine – the daily drawing habit. Learning new things and practicing them takes time, so why not to make this more enjoyable? By the way, remember to add a proper hashtag when posting your artworks for art challenges on social media – you might gather a few new followers 😉

That’s was the list of most popular art challenges. If you know any other interesting art challenges, let me know – I will check them out and add to the list!


*Monthly Art Challenges

Hey, I’ve just recently created a list of monthly challenges (divided by months), and excel – file calendar with the list of monthly art challenges that you can copy. All “non-monthly” challenges will be still added to the current article.

To see the Monthly Art Challenges, click on the image below: 




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