I like Old School Essentials better than any other old-school game, and this includes Shadowdark. I love Shadowdark for its tight, boardgame-style play loop, timers, and 5E-adjacent rules, but OSE is still the king of true classic gaming, including retainers, strongholds, and long-term campaign play.
Shadowdark is great for around-the-table, teamwork, staying tight on time, and tension-filled gaming on a smaller dungeon map. The fact that the whole game never breaks out of initiative order, and players "move around the map" like pieces on a HeroQuest or Monopoly board, is the charm of the design.
Shadowdark is still one of my top-tier games, but OSE is a level above it.
But OSE was designed for the long-term campaign, and the advanced (and 'zine) options take this game to another level. OSE excels in the macro, where you clear hexes, settle domains, put together expeditions of a dozen ships and 400 men to clear the Isle of Dread, and do those "big amazing things" that classic fantasy gaming allowed us to do so well. If you have the gold and leadership skills, you can pay for a small army, specialists, and build a fleet of ships.
The only game that does this better is ACKS II, and that game goes into deep layers of detail. If you want to keep it simple, and houserule things like mass battles (or find a Mass Combat system on DriveThruRPG, of which there are many), then that is also an option. OSE keeps it simple. Some of the zines have more information on hirelings, and those are worth picking up.
And once you include the official 'zines, the number of options and character abilities starts to increase dramatically. With a few of these excellent add-on books, you can have every class and race option players expect in 5E, all done in the best, old-school, classic, simple style that many grew up with. Want dragonborn, drow, or tiefling racial classes, or have them as race-plus-class options? That is in these add-on books.
You can run an entire "D&D 4-style" Nerrath campaign with just the two Advanced Fantasy books plus the five 'zines that have been released for the core game. It has been a while since I found a game worthy of replicating this campaign, but this would work and give me the higher power level I am looking for.
And the books are small, packed full of great stuff, and do not consume shelves of space. The books are small, but have the best layout and page design of any game in roleplaying. When I want "books useful in play," I reach for the OSE books, which instantly make everything understandable and readable in seconds, eliminating the need to page through two pages of AI-generated fluff text.
OSE has far more options than Shadowdark, plus that macro game that defines the old-school experience. Go into the Tomb of Horrors with 50 retainers, torchbearers, treasure haulers, a few sages, some thieves-for-hire, and other experts? Drag mules in there to haul our buckets of gold? Hire a small force of fighters to protect your base camp and treasure horde? Toss in chickens tied to 10-foot poles to scout for traps? Beat the dungeon, then build a stronghold and holy church on it to seal away the evil for eternity?
You can do that in OSE if you spend the gold. Not 5E.
You can't do this level of macro campaigning in Shadowdark, DCC, 5E, or many of these other games. Many of these games force you to "think small" and within the confines of one hero. If I am playing the ultimate "single hero" game, I am playing Dungeon Crawl Classics. I can always port in the campaign rules from OSE if I want, and the two games work together so well that they are very compatible. DCC is a clear 5E replacement in my book, where 5E is very static, stale, and predictable in terms of progression. In DCC, anything can and will happen, and that is emergent gameplay.
If I am playing a "Guild of Heroes" game, can I efficiently run 50 characters on index card character sheets? That game is OSE, and it has all of the best parts of 5E with a tenth of the complexity.
OSE is still a clear winner, easily worthy to replace 5E at any game table, and it does not require a massive investment in money or space to return a lifetime of rewards and fun.
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