min read

Best Guess the Drawing Games

An overview of the different types of drawing games, and how to bring the fun to your workplace!
Updated on
July 12, 2023

In kindergarten, students use crayons, colored pencils, and markers to express themselves. They paint their families, unicorns, and everything else on their mind. Whether they create masterpieces or just oodles of color, these drawings never fail to draw out a smile from those around them.

This magic doesn't disappear over time. Instead, it's stored in each person's inner attic, behind cobwebs and old memories. Adults use a formal language filled with metrics, KPIs, and other abstractions. In the workplace, there's a belief around productivity and function work – where every minute or hour needs to have some measurable output.

Yet, people do their best work when there's an element of playfulness. It's the difference between someone's work life and their life's work. The former is a routine sequence of clocking in and out, the latter produces great products.

In the context of remote companies, it can be hard to create a playful culture. It doesn't show up on the quarterly metrics or the company bottom line, but everyone who works at the company can implicitly or explicitly feel the difference.

There's no better way to create a positive culture than teams drawing together. In the process, coworkers recapture the lost magic that makes each of them individuals. When they draw, they etch out a part of who they are. Each drawing is a sanctuary where they can truly be themselves.

None of these drawings need to be masterpieces. In fact, part of the beauty behind art is its rough edges. When drawing off the cuff, the artist's personality starts to shine through.

So, the question becomes – how can we bring drawing activities to the workplace?

The answer is “guess the drawing” games. Also known as Pictionary. They're fun drawing games where the basic premise is for a player to draw out a given word and for the other players to guess what word is being drawn. The artistic requirements are low enough that everyone, even someone who's drawing skills consistent of doodles, can join and have fun.

Where and when to play

The best part about Pictionary games is that they require very little equipment. Coworkers can start laughing together in minutes with nothing more than an audio connection and a shared sketch board.

Playing the game is simple. All it requires is a group of two or more people. That makes it perfect for one on ones, team bonding sessions, community social gatherings, or even company-wide events. The best part is that, unlike other games, playing online doesn't diminish the joy and energy of Pictionary. They're ideal online drawing games.

So, companies can either choose to play in a conference room, in a small booth, online, or even asynchronously. For remote companies, there are online Pictionary platforms like Skribbl, Gartic, and Sketchful. The only downside to these platforms is that they don't have video. Participants are limited to just the sketch board and chat. For that reason, we suggest a dedicated platform like Fun Country where video is natively built into the gaming experience and coworkers can pick up on visual clues.

Another part of Pictionary is that, unlike traditional board games, each Pictionary party game can be as little as five minutes. So it's a great starting place for companies that want to bring intentional fun to their workdays. It slots in easily and adds a bit of levity to otherwise stale meetings.

Different Guess the Drawing Games

There are multiple variations of guess the drawing games. Some take a bit longer than others and are more geared towards larger parties. In the following sections, we'll break down different Pictionary games and find the best drawing games for meetings of every size.

Classic Pictionary

Classic Pictionary is one of the most popular drawing games that's perfect for groups of 4 - 30 players. The players are split into two or more teams, where each team has at least two players.

Within each team is a single artist and one or more guessers. The artist is given a list of words such as “dog”, “airplane”, and “handstand”, and needs to draw an image representing each word. The team is given a time limit, and the guessers on the team need to guess as many words as possible before time runs out. So, the artist can choose to skip the harder words and start with easier drawings or they could use harder words as a drawing challenge.

The score is calculated as the simple sum of correctly guessed drawings. For example, if team A's artist was given 10 words but the guessers only guessed 3 of them, then team A has a score of 3.

Once every team has had a chance to draw, the round for the game is over. If there's more time for additional rounds, the teams can rotate artists (one of the guessers becomes the new artist) and repeat the process above.

The scores are cumulative and compared against other teams to determine a winner. If team A guessed 3 words in the first round and 5 words in the second round, their total score is 8.

Classic Pictionary is great for team bonding from its variable team aspect. A company can slice the teams in various ways. In one game, it can be engineers on one team and marketers on a different team. Even with uneven player counts, the game is fundamentally the same. Or, the company can mix the teams to be more cross-functional so that different parts of the company interact with each other.

At Fun Country, we offer Classic Pictionary under the name Oodles of Doodles (Team version). We just launched a free trial where anyone can hop in and invite their team to fun in minutes. In fact, if you have a fun Slack channel (we previously wrote about best practices around organizing Slack for connection and fun), Pictionary is a great activity to pop in a channel like #comapny_water-cooler.

Who's the Best Artist

While Classic Pictionary is great, it requires at least four players to function. For smaller games of three or fewer players, Who's the Best Artist becomes the perfect multiplayer drawing game. It's especially good for small meetings, standups, or even 1:1s. The ideal number of players is anywhere from 2 - 10 players.

The basic rules are the same as Classic Pictionary. However, each player is their own team and takes a turn as the artist. The artist position is rotated among the whole group and the game ends when every member of the group has had a turn as the artist.

The points are calculated by the number of correctly guessed words, where the artist who successfully drew the most guessed words is the winner.

This is best for smaller groups where everyone has some level of understanding of each other. For example, a great way to add a bit of fun to everyday engineering standups.

Reverse Artist Pictionary

Reverse Artist Pictionary is almost the same game as Who's the Best Artist and best for 2 - 10 players. However, instead of points accruing to the artist, Reverse Pictionary has the points going to the guessers. The faster a guesser guesses the word, the more points they score.

Each artist is only given a single word to draw and a time limit for guessers to guess the drawing.

Let's take a four-player game as an example. If player B was the artist and given the word “airplane” to draw, he might use silver to draw a body and two wings. When player A correctly guesses the word first, he wins 100 points. Ideally, his answer isn't disclosed to other guessers. So when player B guesses the word, he wins 50 points, and finally, if player C wins 25 points when he guesses the word.

This difference has catapulted Reverse Artist Pictionary to be one of the most popular drawing games among Pictionary variations. Further, because Reverse Artist Pictionary needs a secrecy component, online drawing platforms like Skribbl.io allow groups to play without planning additional logistics. In fact, there are a wide range of platforms that support Reverse Artist Pictionary. We'll go through some of the more popular drawing game websites below.


A retro-style Reverse Artist Pictionary game. The maximum number of players in each of Skribbl's rooms is 20, and the artist can choose from one of five words to draw.

Of the free platforms, Skribbl is one of the best. Its drawing board is quick, responsive, and has multiple drawing tools for the artist.


Like Skribbl, Sketchful sports a rather hand-drawn style. The mechanics of the drawing board and guessing are relatively the same.

But where Sketchful shines through is the fact that players can take screenshots of the drawings to save for later. Teams can save the pictures to add as Slack emojis for their workspace and remember the laughter when playing together. Or, they can be saved as unique digital art for a company's scrapbook.


Unlike the former two, Drawsaurus sports a relatively modern aesthetic. The drawing board is quite minimalistic.

However, the feature set of Drawsaurus is relatively limited. Players can still have a fun time, but the games feel less engaging compared to other online drawing games.


The main feature of Gartic is that it shows when a player's guess is close to the correct word. However, the platform has the option to hide the number of letters in the word to be guessed which dramatically increases the difficulty level of games.

Further, Gartic institutes a break interval in between each game. While it's great for teams to bond, it also slows the pace of the game down significantly.


Drawize's primary advantage is that up to 100 players can play in a private room. However, the main downside is an incessant feed of ads where players need to purchase an ad-free tier.

The game also features a style that feels a bit more targeted toward children rather than adults.

Fun Country - Oodles of Doodles (Classic)

Our favorite. Compared to the other platforms, Fun Country has a built-in video component. This makes it more ideal for teams who now can all interact on the same platform rather than stitch together multiple tools.

Sketch Emoji

Sketch Emoji is one of the most popular drawing games. It takes the traditional Pictionary and adds a twist. Instead of being given a word, the artist is now given an emoji and without replicating the emoji, they need to draw an image for others to guess the emoji.

The main benefit of Sketch Emoji over the other forms of Pictionary is the expressiveness of the drawings. In Pictionary, the words are often nouns which have a more defined image associated with them. However, an emoji like 😀 is hard to showcase in a single drawing. The artist might choose to draw a pool and point at the people around the pool to express happiness, or they might draw stick figures telling a joke. The opportunities are endless.

The other part to Sketch Emoji is that it can work with any of the Pictionary formats. It can replace Classic Pictionary, Who's the Best Artist, or even Reverse Artist Pictionary. It's an ideal fun drawing game that can fit into a wide range of group sizes.

Quick Draw

Quick Draw is the only single-player Pictionary game at the moment.

Powered by Google, Quick Draw has an AI algorithm try to guess what the artist's drawings represent. Given six words, one at a time, the player creates drawings for the AI to recognize.

The unique part of Quick Draw is the fact that the AI algorithm will list out their guesses at the bottom. So as the player sketches their drawing, they can reinforce certain concepts and improve their artwork as the timer runs down. It's a great way to think about and understand how to visually represent certain words or concepts, as well as a drawing challenge to relax.

As a whole, Quick Draw is best for a small meeting where the non-artists can watch along and offer suggestions. Or, it could be a quick pick-me-up for someone who has a bit of downtime and wants to add a bit of fun to their workday.

Final Thoughts

Pictionary and the variations on it are an artistic challenge, they're also a way for coworkers to safely express themselves amid laughs. It's a great way for teams to bond and cheer each other on.

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