Cool Art Challenges | List of Most Popular Ideas

If you’re hitting a rut in your artistic journey, overwhelmed by too many options, or are simply looking for a way to draw every day, an art challenge may be a solution for you.

Art challenges are trials that artists can take on to test their skills and connect with the online art community. Creators of art challenges define the rules for the challenges and encourage others to participate through the use of online posts and hashtags.

Sometimes the hosts of each challenge offer prizes and features, but the real benefit of art challenges is the community engagement, honing your artistic skills, and finding your own art style.

Here are the 10 most popular art challenges in 2021:


Perhaps one of the most famous art challenges is Inktober. This challenge began in October 2009 when artist Jake Parker made the announcement on his blog. The original challenge was created so that Parker and others could develop their inking skills, and he encouraged participants to share their work using the hashtag #Inktober.

Inktober consists of making one ink drawing every day in October, which encourages good daily drawing habits from those who chose to participate. In 2016, Parker introduced a list of prompts to help artists spark new ideas each day. Though it was originally meant to be done with ink, Inktober challenges can be done digitally or with virtually any medium, as the goal is to simply make a drawing each day of the month.

Inktober took the art community by storm and sparked many “spinoff” challenges. For example, Huevember consists of drawing in a different color for each day in November, and MerMay involves drawing a new mermaid design every day in May.

With all of these spinoffs, you’ll likely be able to find a challenge going on right now. You can use a daily prompt to guide you, combine multiple prompt lists, or simply generate your own ideas. Use this challenge to make drawing a part of your day.

100 Heads Challenge

Heads and faces are notoriously one of the hardest things to draw. The 100 heads challenge aims to be a crash course in perfecting the anatomy of the human head, as well as practicing different face shapes and expressions. Artist Ahmed Aldoori created the challenge of drawing 100 heads in 10 days, meaning artists should draw about 10 heads per day to keep up.

This can be a rigorous gauntlet, but it’s meant to improve your skills quickly and force you to practice using references. Aldoori created an official Pinterest board to help get you started, but there are thousands of face references on the internet at your disposal, so you can easily supplement the board with other faces that you want to draw.

In the end, this challenge will require some planning. It takes time to gather reference material, and it will take a significant chunk out of your day to draw at least 10 faces. However, the results will come very quickly, and tagging your art with #meds100heads will allow you to connect with others who attempt the challenge.

Different Art Style Challenge

The #StyleChallenge was started by an Instagrammer named beautifulness87. This challenge involves drawing the same character, or sometimes yourself, using several popular and instantly recognizable different art styles. Then, as with most drawing challenges, you post the result online and share it using the appropriate hashtags.

Commonly seen styles used in this challenge are the Powerpuff Girls-style, the Adventure Time style, the anime style, Steven Universe style, and the Simpsons style. This challenge is often found in the form of a downloadable template, which will give you 9 different styles to draw.

This challenge is a great way to flex your cartoonist’s muscles. There are endless ways to depict a character, and pulling from successful styles may help influence and guide your own style choices.

Left-Hand Challenge

The goal of this challenge is pretty simple – using your left hand, draw a piece of art. The “why” behind this challenge may be a little harder to understand. Why draw with your left hand when your right-hand works perfectly fine?

Ferdouse Khaleque explains that he attempted a 30-day left-handed drawing challenge because he initially wanted to give his right hand a break from drawing. After a few uncomfortable sketches, he found that he was much better with his left hand than he thought he would be.

Drawing with your left hand (or your right hand, if you are naturally left-handed) is a great way to see the world differently. If you choose to keep going past the uncomfortable feeling, you may unlock and cultivate a new skill that you didn’t know you had before. At the very least, doing a drawing with your left hand will humble you and maybe make you chuckle a bit as well.

Draw This Again Challenge

Almost nothing is more inspiring than watching your own artistic growth. The Draw This Again challenge is a challenge that involves re-drawing a previous piece of artwork again in the exact same way. This will quickly allow you to see how much your skills have grown since you attempted the first piece of art.

You have a large range of options when it comes to choosing what to draw next. Some people choose a piece of art that they did when they were very young. If you don’t have extremely old artwork, try drawing a piece that you created at the start of your artistic journey.

Finally, artists sometimes re-do this challenge year after year with the same piece of artwork as a base. This allows them to have a concrete marker of their growth as an artist as they watch the same piece improve with each passing year.

ToonMe challenge

René Córdova, an illustrator for Marvel, created the ToonMe challenge in January 2020. She shared a selfie that was half photograph and half illustration, and the ToonMe challenge was born. Artists all over the internet began to use their selfies to create works of art in various cartoon styles.

The ToonMe challenge works best with digital art programs, but crafty traditional artists can still make it work. Begin with a photo of yourself and add another layer on top. Trace over half of your selfie in a cartoon style, or any style that you like.

The goal here is to draw a juxtaposition between the artist and the art style that they employ. ToonMe challenges are also a great way to show your online audience what you look like in a fun, art-themed way. You can get extremely creative with the types of details and features you add to the illustrated side of your selfie.

Because you can simply trace over your selfie as a direct reference, this challenge is relatively low-stakes, but still a good deal of fun.

Draw This in Your Style

Like Inktober, the Draw This in Your Style challenged (shortened to DTIYS) became very popular in the art community, but it can be done any time of the year. Artists will post a piece, either a favorite work of theirs or a piece they created just for the challenge and encourage other artists to replicate the work in their own style.

This type of challenge benefits both the original artist and the artists that participate. There are often no limits to a DTIYS, so you can take the derivative drawing as far as you like as long as it was clearly inspired by the original work. And, with so many replicas of the original idea going around (with credit given, of course), then the original artwork and artist are bound to get a lot of attention.

DTIYS challenges are also a great way to build community. Artists will often create their own hashtags for entries and feature their favorites. Everyone who participates in a DTIYS challenge can come together over the work of a prolific artist.

3 Markers Challenge

Limitation is at the heart of most of these art challenges, whether it is limiting when you draw or what you draw. The 3 Marker challenge is no exception. This challenge involves drawing a sketch or a lineart, picking 3 markers, and finishing the drawing using only those three colors (though some artists also allow black or white to be used in the illustration).

Because the three colors you choose are random, artists are required to utilize every skill they have when it comes to manipulating and using color effectively. The mood that you had in mind for your sketch may drastically change depending on what colors you choose. You will also be presented with an extra challenge if you get three very similar colors or three colors that are radically different and clash when mixed together.

If you don’t have markers, don’t let that limit you. You can do this challenge with three paint colors or three colored pencil colors as well. If you’re a digital artist, you can use an online generator to create three random colors to use in a digital piece.

6 Fan Arts Challenge

Started in March of 2020 by Twitter artist Melissa (@mcapriglionart), this challenge is about drawing different popular characters in your style. Melissa began by asking her audience which 6 characters she should draw in her own unique style, and other people began asking their audiences as well and doing the same. Melissa then created a template that artists can use when drawing their 6 characters.

This challenge is almost like the opposite of the Art Style challenge mentioned above. rather than converting your character into different, popular art styles, you take popular characters and convert them into your own style.

This challenge is a fun way to explore new characters that you may not have otherwise thought to draw. If you have an online audience, you can ask them what to draw, and they’ll be able to see your rendition of their favorite characters.

Painting With One Layer Digital Art Challenge

Once again, limitation sparks creativity in these art challenges. Digital art is nearly limitless in the number of colors and brushes one can use, especially with the addition of layers. Layers are like transparent “sheets” that you can stack on top of one another to add depth and complicated effects to your digital drawing.

Many digital artists use layers in a very methodical way to make their drawing process more efficient. They assist with accuracy and make sure the colors stay within the lines, or that the shading can be easily adjusted.

For artists who ordinarily use layers to their full potential, drawing on only one layer can push them to be thoughtful about their color choice and application. Because they lose a significant amount of the effects by eliminating the use of layers, this challenge is exciting because it forces digital artists to think more like traditional painters. It can help them see their artwork in a new light, and develop interesting techniques that they may not have discovered otherwise.

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