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The adventure follows the general story arch of the original tale, where King Richard the Lionheart has been taken hostage on his way back from The Crusades. Your primary task throughout the game is to collect enough money to pay the king's ransom, while fighting against the oppression of King John and the Sheriff of Nottingham. Some of the story, particularly the role of Maid Marion, has been altered, adding elements of druidic mythology.
During the game, Robin must prove his ability to fight in hand-to-hand combat (with a staff) and of course his superior marksmanship with the longbow. Tactical thinking is also required, as several times in the game you'll be counseled by your merry men about possible approaches to an impending battle where only one will result in no casualties to your men. Various actions will win money towards the ransom, and there are multiple endings based on the amount of money you've raised and the actions you've taken during the adventure.
Overall, this is a somewhat Darker and Edgier version of the popular legend, and is widely considered to be more difficult than the average Sierra adventures of the time. Particular scenes, such as the Nine-Men-Morris minigame, can be quite frustrating to adventure players, although the action scenes can be skipped by lowering their difficulty.
This game provides examples of:
- Berserk Button: If you're the Sheriff of Nottingham and a "guest" at one of the banquets of the Merry Men, it's probably not a good idea to tell Robin you're an agent of King Richard.
- Bookcase Passage: Not a bookcase, but there's a secret passage leading from the tavern to the monastery. Now you know what the monks do with their free time. That passage also leads to a secret door in the castle.
- Character Witness: At the end, if you do things right. Doing it wrong can result in negative testimony.
- Copy Protection: Four times: Hand Code, gemstone lore, coats of arms identification, and Latin tree names.
- Corrupt Church: Every religious person in the game, aside from Friar Tuck.
- Damsel in Distress: Marian. The player first meets her when she's being attacked by an evil monk; later she needs to be saved from being burnt at the stake.
- Did Not Get the Girl: You can let Marian die at one point and still finish the game. Plus, unless you get the Golden Ending, you won't be able to marry her.
- Due to the Dead: Robin ensures that Friar Tuck gives a proper burial to all the people he kills in the forest and on the highway - except one.
- Drinking Contest: The Abbott challenges you to one.
- Drowning My Sorrows: Robin does this at the beginning because he's lonely.
- Elemental Powers: The rings of protection from fire and water.
- Evil Debt Collector: Everyone's favorite Sheriff of Nottingham, of course.
- Fens Are Evil: More specifically, haunted by wisps and home to an evil monastic order. Subverted as the wisps help you if you wear the Ring of Water.
- Flower Motifs: Several puzzles involve these.
- Friend to All Living Things: Marian, who in this version of the story is a priestess of the forest.
- Gaia's Vengeance: Mess with Green Man and he'll turn you into a tree.
- Girl of My Dreams: Marian first appears to Robin in a dream.
- Hedge Maze: At the back of the Nottingham abbey.
- Let's Play: The good people at Transmission Awesome did one of these, later uploading the entire recordings, dubbing it "The Whole Shebang Edition. Links to parts 1-7 can be found here, whilst parts 8 and 9 are here and here, respectively.
- Have a Nice Death: In a twist from the usual Sierra formula, the game's death sequences show the Merry Men commenting upon how Robin died, usually offering a hint on how to avoid repeating the same mistake.
- The Jester: Fulk, to King Richard
- The Lost Woods: Sherwood Forest
- The Many Deaths of You: It's a Sierra game. Par for the course, really.
- Master of Disguise: Robin.
- Multiple Endings: Again, it's Sierra.
- Nature Spirit: The Green Man.
- Optional Sexual Encounter: If you make Marian look at an emerald before the Archery Contest, you get one of these.
- Rape Is a Special Kind of Evil: Robin had the corpse of the guard who tried to rape a woman dragged off for the wolves instead of properly buried.
- Riddle Me This: To learn disguising magic from Green Man. Also, you're restricted to answering in Hand Code.
- Sexy Discretion Shot: Done with the Optional Sexual Encounter. Lampshaded by the game, citing their need for privacy.
- Stealth Insult: Robin Hood, disguised as a monk, "blesses" the Sheriff to "get all he deserves and may (Robin) live to see it." Being drunk, the Sheriff thanks and tips him, the Merry Men speculating at camp that he'd be furious when it finally clicked.
- Those Two Bad Guys: Roger and Giles.
- Too Dumb to Live: "You see, I'm nearly safe, but I thought I'd do something truly foolish instead and get myself killed."
- Unwinnable by Design: It's a Sierra game.
- You Need to Get Laid: Robin's friends suggest that the reason he's depressed is that he's missing the company of a woman.