Artistic Tolkien fans united on twitter this year for #Tolkientober to share new illustrations and representations of Middle-earth. Both fun and personal, the charge was led by Molly Ostertag who here pulls a small sample of the 1000’s of outstanding drawings.

EDITORS NOTE: Guest author Molly Knox Ostertag was invited to showcase the great artistic work done by fans worldwide for #Tolkientober. She is one of 2020’s Forbes 30 Under 30 media professionals, a NYTimes best-selling author and a leading illustrator for Disney animation.

A common theme of 2020 (besides mounting existential dread and the strange feeling that it’s lasted several centuries) has been people finding comfort in a return to their teenage passions. This is my sole excuse for why I have become as obsessed with Lord of the Rings this year as I was when I was 12 and would literally lie on the floor with giant speakers on either side of my head, playing the Return of the King soundtrack and crying about the Grey Havens. 

I’ve been having fun drawing and writing and indulging this obsession, but there’s a limit to how much hobbit fanart a bored lesbian in lockdown can produce. Craving more content in much the same way Thorin & Co crave their ancestral treasure, I started a drawing challenge for October called #Tolkientober (I couldn’t think of a better name; please let me know if you come up with one). Each day had a theme, sometimes obvious things like ‘a dwarf’ and sometimes more interpretative, like ‘a guardian’. With weekends off, of course – no one better than Tolkien understood the importance of having periods of rest and healing in between efforts.

Hobbits as Children by Molly Ostertag

I’ve never participated in this fandom before in a major way, and it has been lovely and exciting to see how alive it is after all these years. There is just something open about Middle-Earth, something that invites us to explore, adventure, and make ourselves at home. This wide-open feeling is a rare quality to stories, but it makes sense that Lord of the Rings has it. The best stories (the ones that really matter, as Samwise would say) have sticking power, and generations of readers can find unique and personal meaning in the tale. There’s magic in reading words from long ago that nevertheless feel like they were written for you, in this moment, right now.

As Tolkien wrote in Letter 131: “I would draw some of the great tales in fullness, and leave many only placed in the scheme, and sketched. The cycles should be linked to a majestic whole, and yet leave scope for other minds and hands, wielding paint and music and drama.” What a beautiful way to describe fanart and the tradition of keeping a world alive. Here are some of my favorite pieces from Tolkientober:

Day 1 – favorite character

Day 2 – yourself in middle-earth

Day 5 – a hobbit

Day 6 – royalty

Day 7 – a character in our world

Day 8 – a favorite scene

Day 9 – a dwarf

Day 12 – two characters who are in love

Day 13 – an elf

Day 14 – illustrate a headcanon

Day 15 – a warrior

Day 16 – a character as a child

Day 19 – a villain

Day 20 – where you’d live in middle-earth

Day 21 – magic

Day 22 – a man

Day 23 – redraw a piece of tolkien’s art

Day 26 – best friends

Day 27 – a creature

Day 28 – a guardian

Day 29 – a ringbearer

Day 30 – home

Molly Ostertag is a NYTimes Best Selling author, graphic novelist, and animation pioneer for shows like OWL HOUSE and THUNDERCATS ROAR. You can follow her on twitter @MollyOstertag or her Tolkien-themed alt @hobbitgay