- Ensemble Dark Horse:
- Ellie in Complex has gotten more than her fair share of attention from the fans, with many wanting to see her in future games. Too bad the very next game after her debut will be the Grand Finale! (But on the bright side, Ellie has been confirmed to appear in it!)
- Most of the fans love Charles, for his hilarious Too Dumb to Live moments and his dynamic with Henry.
- Fan-Preferred Couple: Henry and Ellie, unsurprisingly, given how well they work together in Complex and the fact that Ellie is pretty much the only female character Henry's ever interacted with.
- Growing the Beard: The first two games (Crossing the Pit and Breaking the Bank) are rather simplistic. Escaping the Prison introduced an ongoing story line (albeit one that is heavily subjected to Shrug of God), as well as Easter Eggs and Multiple Endings to spice things up and make the games more engaging.
- Hilarious in Hindsight: In Complex, one of the fails is Henry kneeing Ellie and the warden, knocking them out of the arena Super Smash Bros. style, and then the victory screen from Street Fighter II shows up after which the FAIL screen scolds Henry for "mixing fighting game references". And then Ryu becomes a playable character in the fourth Super Smash Bros. game...
- Jerkass Woobie: Henry may be a thief and criminal, but it's hard not to feel bad for him whenever the items he has at his disposal screw him over.
- Memetic Mutation: THIS IS THE GREATEST PLAAAAAAAAN!!!!!
- Charles in general.
- Older Than They Think: The Toppat Clan's appearance goes as far back as 2007 in this animation.
- In Infiltrating the Airship, when playing through the earpiece route, Henry eventually has his ally Charles take out a mook by literally melting his bones! The poor guy is reduced to a lump of flesh as a result.
- One particular option in Fleeing the Complex involves Henry pretending to be sick in the hopes of finding a way to escape. He's tranquilized by a guard and left in a quarantine cell with an unknown number of inmates, presumably infected with debilitating or even lethal illnesses. The inmate that greets Henry when he wakes up actually loses his hand, and when we see the quarantine cell from the outside, a green liquid is pooling out from underneath the door.
- Another involves Henry bungee jumping down an elevator, resulting in his back getting ripped out since he's using an ordinary rope.
- Tear Jerker:
- Nearly all of the fails are Played for Laughs, but one particular fail in Infiltrating the Airship is Played for Drama instead. After the airship crashes outside their headquarters and a massive battle starts, an agent of the Center for Chaos Containment fires a Dark Energy Blaster. However, the blast disintegrates everything and everyone, including the CCC-headquarters and those in it. While sad background music plays, the agent takes one last look at a picture of his family while tears form in his eyes, and sadly bids them goodbye as the blast envelops him. Even the fail screen has nothing to say to this...
- The Betrayed ending in Complex. Henry calls in the Toppat Clan to bust him out of the complex, making a daring escape on his scooter. His lieutenant catches him before he misses the jump, but then announces he'd rather have his old position as Head of the Clan back and drops Henry to his apparent doom. And to make it worse, Word of God confirmed that Henry dies in this ending.
- What an Idiot!: Many fails are results of this. Luckily, it makes them funnier. Special mention goes to Charles; during the scenarios in which he assists Henry, pretty much all fails are a result of him screwing up rather than a mistake from Henry or equipment malfunctioning. For example:
- In Airship and Complex, Henry asks Charles to directly get him. He crashes into where Henry's standing.
- In Complex, Henry asks Charles to snipe down one of the guards. He mistakes Henry for a Guard and shoots him instead.
- When Henry decides to have Charles catch him while he falls down, Charles doesn't realize what's going on and just hovers in place. A guard then blows Charles up with a rocket launcher mid-sentence.
- Henry asks Charles to use some of his gadgets to help him in Airship. Asking for the platform makes him Teleporter Accident it straight into Henry's body. Using the Gravity Bubble causes him to crush Henry with itnote , Mind Control causes Charles to make his subject break the card he's using, and Remote Hacking causes him to hack the wrong door, which smashes Henry when it opens.
YMMV / Henry Stickmin Series