With the recent release of the 2021 ENNIE Award nominations (The Waking of Willowby Hall was nominated for Best Adventure!), I thought I’d take a look back through the award’s history to see how the OSR has historically fared. I’ve listed all OSR and OSR-adjacent products that have been nominated since 2010 below. If they have 1 star, they won silver in their category. If they have 2 stars, they won gold. Of course, what counts as “OSR” is a matter of personal opinion, so other people might count this differently. My list starts at 2010 because prior to that the only OSR-ish products appear to be books by Goodman Games and Necromancer Games, who were using 3.5 for their rules.

2010 – 3 Nominations, 0 Wins
The Grinding Gear – Best Adventure
(Honorable mention) Death Frost Doom – Best Cartography
(Honorable mention) Labyrinth Lord – Best Game

2011 – 2 Nominations, 1 Win
**Old School Hack – Best Free Product
(Honorable mention) Stars Without Number – Best New Game

2012 – 0 Nominations, 0 Wins

2013 – 5 Nominations, 0 Wins
The Magnificent Joop van Ooms – Best Art
Astonishing Swordsmen and Sorcerers of Hyperborea – Best Game
Astonishing Swordsmen and Sorcerers of Hyperborea – Best Production values
Astonishing Swordsmen and Sorcerers of Hyperborea – Product of the year
Goodman Games – Favorite Publisher

2014 – 1 Nomination, 0 Wins
Old School Monsters Database – Best Software

2015 – 4 Nominations, 4 Wins
*A Red & Pleasant Land – Best Adventure
*A Red & Pleasant Land – Product of the Year
**A Red & Pleasant Land – Best Setting
**A Red & Pleasant Land – Best Writing

2016 – 5 Nominations, 3 Wins
Maze of the Blue Medusa – Best Adventure
*Maze of the Blue Medusa – Best Cartography
**Maze of the Blue Medusa – Best Electronic Book
*Maze of the Blue Medusa – Best Writing
Maze of the Blue Medusa – Product of the Year

2017 – 7 Nominations, 4 Wins
**Broodmother Skyfortress – Judge’s Spotlight
**Blood in the Chocolate – Best Adventure
The Cursed Chateau – Best Cartography
*Veins of the Earth – Best Adversary
Veins of the Earth – Best Rules
*Veins of the Earth – Best Writing
Veins of the Earth – Product of the Year

2018 – 15 Nominations, 8 Wins
Fever Swamp – Judge’s Spotlight
Operation Unfathomable – Judge’s Spotlight
**The Dark of Hot Springs Island – Best Adventure
*Frostbitten and Mutilated – Best Interior Art
**The Midderlands – Best Cartography
*Scenario from Ontario – Best Electronic Book
Vaginas Are Magic – Best Free Product
**Frostbitten and Mutilated – Best Monster
Rey and Kiel Can Do – Best Podcast
Hobbs and Friends of the OSR – Best Podcast
*Fear of a Black Dragon – Best Podcast
*Frostbitten and Mutilated – Best Setting
*Frostbitten and Mutilated – Best Writing
The Dark of Hot Springs Island – Product of the Year
Frostbitten and Mutilated – Product of the Year

2019 – 17 Nominations, 5 Wins
The Stygian Library – Judge’s Spotlight
*Mothership: Dead Planet – Best Adventure
Winter’s Daughter – Best Adventure
Winter’s daughter – Best Cover art
*A New Map of Hot Springs Island – Cartography
Silent Titans – Cartography
Midderlands Expanded – Cartography
*The Ultraviolet Grasslands – Best Free Product
**Mothership – Best Game
*The Black Hack 2nd Edition – Best Layout/Design
Questing Beast – Best Online Content
Silent Titans – Best Production Values
Mothership – Best Rules
Silent Titans – Best Writing
Troika – Best Writing
Mothership – Product of the year
Silent Titans – Product of the year

2020 – 19 Nominations, 11 Wins
**A Pound of Flesh – Best Adventure
The Halls of Arden Vul Complete – Best Adventure
*Trilemma Adventures – Best Adventure
*Ultraviolet Grasslands – Best Cover Art
**Ultraviolet Grasslands – Best Interior Art
**Trilemma Adventures – Best Cartography
*Tunnel Goons – Best Free Game
*Mork Borg – Best Game
*A Pound of Flesh – Best Layout
**Mork Borg – Best Layout
Trilemma Adventures – Best Layout
Worm Witch – Best Monster
Old School Essentials Generators – Best Online Content
Appendix N Book Club – Best Podcast
Rakehell – Best Setting
Electric Bastionland – Best Writing
**Mork Borg – Best Writing
**Mork Borg – Product of the Year
Trilemma Adventures – Product of the Year

2021 – 16 Nominations, ? Wins
The Waking of Willowby Hall – Best Adventure
Halls of the Blood King – Best Adventure
DNDNGEN – Best Aid/Accessory – Digital
Neverland – Best Art, Cover
Neverland – Best Art, Interior
Halls of the Blood King – Best Cartography
Undying Sands – Best Cartography
Mausritter: Boxed Set – Best Family Game/Product
The Stygian Library: Remastered – Best Layout and Design
DNDNGEN – Best Online Content
Worldbuilder’s Notebook – Best RPG Related Product
The Stygian Library: Remastered – Best Setting
Undying Sands – Best Setting
MÖRK BORG CULT: Feretory – Best Supplement
The Stygian Library: Remastered – Best Writing
The Stygian Library: Remastered – Product of the Year


In 2020 the OSR had almost 17% of all ENNIE nominations and 26% of all wins (and it would be even higher if I included OSR-inspired stuff like Labyrinth). 2020 was also the peak of a seven year run where the number of OSR nominations increased year after year.

I would be curious to see how Forge-derived games or storygames have done over time (my impression is that they have become much more popular in recent years) but I don’t know enough about them to tell which books would fall into that category.