- In the first game, Shantae needs to get help from her friends and other NPCs to unlock the dungeons. The methods they choose to do so can be pretty silly:
- For the Water Dungeon, Bolo flings his weapon which bounces around everywhere before hitting the eye above the door.
- For the Earth Dungeon, Sky's bird Wrench literally acts as a wrench, screwing in two gems along the wall to unlock the door.
- For the Zombie Dungeon, Rottytops detaches her leg and uses it as a makeshift lockpick.
- And finally for the Ice Dungeon, the Bandit Town Genie just smacks the gate with her hip, which unlocks it.
- Shantae thanking Barracuda Joe for his generosity in Risky's Revenge.
Shantae: Thanks Barracuda Joe! You're a lifesaver! (Kiss!)
Barracuda Joe: Don't say "kiss" to me unless you're actually givin' me a kiss. Otherwise it's just words. Okay?
Shantae: Ok. (Kiss!)
Barracuda Joe: Ok, yer doing it again. Get going.
- The increasingly grandiose rant of the chef girl in the Forest if you refuse to give Wobble Bell back.
Chef Girl: You're right. That's probably not my pup. Oh, Wobble Bell! If only I knew where he went! He probably felt that I took him for granted and left to find some other chef to inspire! And now, they are making wondrous dishes together and traveling the world. And let's be honest. I was taking him for granted. I rarely even fed him. And when he wanted attention I'd just push him aside and focus on my culinary arts. But now he's moved on, and my fate is sealed. Sure, I'll cook, at first out of habit. But eventually I'll become a heartless automaton, marrying the first man that takes interest and I'll cook and I'll cook. People will come for miles to try my recipes, I'll be famous, and the world will become reliant on my food. Then Wobble Bell and I will meet at random and it will be awkward. I'll bury my feelings until one day I crack. And that will be it. I'll give up cooking and the world will have nothing to eat, and every living thing will starve and die out. The land will grow cold and life as we know it will cease. Oh Wobble Bell, please come back.
- After defeating the Ammo Baron in the intro mission, Shantae is arrested by the Royal Guards and has her "Scuttle Town Guardian" status revoked. They serve her a Court Summons, which she holds up cheerfully like any other key item (complete with Item Get jingle), even though she knows she's about to be placed on house arrest.
- After the first boss battle, Shantae has been through quite a day and decides to take a nice bath to relax and unwind.
Shantae: Wait a minute. I don't own a bathtub.
- The game implies that Risky pushed Shantae, naked and trapped in a bathtub, halfway across town to Mimic's house. And no one noticed.
- Shantae raids Risky's wardrobe:
Shantae: There's all kinds of fun things to play with. Most of the clothes were much too roomy for me, though...Risky: Stay out of my personal effects!
- In Saliva Island, the path to the first Den of Evil opens up by helping a man get a Petrify Spell to bring back his wife turned into stone. Using the spell ends up turning the man into a stone as well, and the sheer weight of both of them causes a hole to open to the dungeon. Shantae can only mutter an embarrassed murmur.
- Sky hooking up with Barracuda Joe. Her dad comments that she could actually do a ''lot worse'' and her mother can't wait to have grandchildren already.
Sky: You want me to stay single forever!
- It gets even better when Sky's dad brings a mummy coffin and has Joe read what it says there. Joe ends up being cursed to the bone by turning into stone, which makes Sky say this:
Sky's Mom: Oh dear. Another boyfriend down the drain...
- Which is immediately followed by this, implying that something this bad has happened before:
Sky: COME BACK AND MARRY ME, YOU SCUMBAG!!!
- Later on, when Shantae helps Barracuda Joe out of his problem (while also doing a Brick Joke of the other incident she caused much earlier) and Sky voices her eternal gratitude to Shantae...Joe blankly dumps her and walks out of her house, much to her annoyance.
- In the credits of the game, Sky seems to have found a new crush in Brandon, complete with Bolo looking annoyed and her parents spying on them from behind a house.
- The Squid Baron spends the first half of the game depressed due to "post-boss syndrome" and you have to keep cheering him up until you eventually fight him at the end of the Lost Catacombs dungeon. The battle begins with him giving an impassioned speech about how he's finally embraced his destiny as a filler boss, and he gets his own frantic music as well as an armored second phase announced with "SQUID BARON 2.0" scrolling across the screen and him holding up sparklers. The battle ends up completely invigorating his fighting spirit and he becomes excited at the prospect of becoming a palette swap or a Degraded Boss.
Squid Baron: Answer me this. How much map have you traveled? How full are your pockets? About half, right? Halfway full? Filler boss. It's my destiny. I see that now. I won't try to escape it.Shantae: You're scaring me...Squid Baron: You and me both. But I won't hide from fate! I'm going to be the best filler boss of all time! Old hat! Recycled moves! All of it! Bring it on, sister! Let's boogie down!
- Shantae feeling jealous and depressed about Brandon's epic adventures. She defines herself as being a bad influence for having a bad temper and dressing inappropriately.
- Obtaining Risky's...Boots?
- When Risky gets taken by the Pirate Master late in the game, Shantae immediately raids Risky's closet again, complete with hilariously bad pirate-speak when commanding the Tinkertub!
- You fix the light puzzle on Saliva Island by getting two extremely white girls to take their clothes off, so that the light reflects off of them brightly enough to activate the machinery. Tell me that's something you read everyday.
- The Tan Line Temple stage sets the stage for a hilarious joke. When Shantae enters, the temple's residents mistake her for their missing princess, and forced into a Chainmail Bikini for her upcoming coronation (Which she calls being "dressed like a Space Princess", in a Shout-Out to the Slave Leia scene from Return of the Jedi.). During her escape, she learns that Risky Boots, Sky, and Rottytops have all ended up in the same situation. After reaching the end, they find a giant statue of the princess- and she looks nothing like our girls. However, the High Priest still insists that the girls are exact doubles for his TITANIC, CORPULENT princess, leading Risky to wanting to throttle him. Then the princess appears! With a bag of groceries! She'd just went shopping, half an hour ago!
High Priest: Our princess has retur-Shantae: [Angrily] Ah, shut yer yap!
- What's also good is the dialogue when you speak to the High Priest afterward-