All of Flynn Ryder's expressions before the Character Development kicks in. Whether completely deadpan or trying to be charming, he's hilarious even when not speaking.
For roughly the first half of the film, he has an unbreaking look of pure misery on his face during every musical number, even when he's just hovering in the background. Never so much as a twitch. It's great.
Rapunzel's little rejoicing/crying episodes after leaving the tower with Flynn. Helped, of course, by Flynn standing in the background utterly deadpan. You really get the impression it's happening as fast for him as it is for us.
Rapunzel: I can't believe I did this! [whispers] I can't believe I did this. I CAN'T BELIEVE IDIDTHIS! Mother will be so furious! [admiring some flowers] That's okay, I mean what she doesn't know won't kill her, right? [hiding in a cave, rocking back and forth] Oh, my gosh! This would kill her! [running around] THIS IS SOOOOO FUUUUUUN! [head leaning against a tree] I...am a horrible daughter. I'm going back. [rolling down a hill] I am NEVER going back! Whoo-hoo! [face down in the grass] I am a despicable human being! [swinging from her hair around a tree] WHOO-HOO! BEST! DAY! EVER! [ends scene with herself sitting beside a rock, crying]
Rapunzel: Break her heart? Flynn: In half. Rapunzel: Crush her soul? Flynn: [crushes grape] Like a grape.
Flynn's expression is what makes this so funny- it really has to be seen.
Flynn: All right. I can't believe I'm saying this, but I'm letting you out of the deal. Rapunzel: What? Flynn: That's right, but don't thank me. [picks up frying pan and Pascal] Let's just turn around and get you home. Here's your pan, here's your frog. (starts walking her) I get back my satchel, you get back your mother-daughter relationship based on mutual trust, and voila, we part ways as unlikely friends. Rapunzel: [stops walking] No! I am seeing those lanterns. Flynn:OH COME ON! What is it going to take for me to get my satchel back?! Rapunzel:(holding frying pan to Flynn's face) I will use this.
Every other thing out of Flynn's mouth.
Flynn: Stay calm. It can probably smell fear. [on the topic of a bunny]
Flynn: Is that blood in your mustache? Hey Goldie, look at all the blood in his mustache! Good sir, that is a lot of blood!
Flynn: And after years and years of asking and asking and asking... I finally said yes! note This is promptly followed by Rapunzel making him tell the truth; "I asked her".
Mother Gothel's talk with Rapunzel.
Mother Gothel: [looking into a mirror with Rapunzel] I see a strong, confident, beautiful young lady. [beat] Oh look, you're here too!
All of Flynn's reactions to Rapunzel's glowing hair: in the water, out of the water, and by the campfire. Especially when he manages to barely suppress a scream and turn it into a high-pitched, borderline panicked set of questions. Comedic gold.
Rapunzel: We made it! Flynn: [completely in shock] Her hair glows! Rapunzel: We're alive! We're alive! Flynn: I didn't see that coming. Rapunzel: Eugene. Flynn: Her hair actually glows! Rapunzel: Eugene. Flynn:Why does her hair glow!? Rapunzel: Eugene! Flynn: [hysterical] WHAT!? Rapunzel: It doesn't just glow. Flynn: [glances at a smiling Pascal] Why is he smiling at me?
Not to mention his reaction to Rapunzel's power a few moments later.
"So! Hey can I ask you something? Is there any chance that I'm going to get super strength in my hand? Because I'm not gonna lie, that would be stupendous"
Flynn's completely non-amused face during the musical sequence in the Duckling bar.
Flynn: I don't sing. [swords point at him from everywhere] Flynn: [commence singing]
Something that makes this moment even funnier is that Flynn is breathless in his singing, since he's quite literally forced into it at sword-point!
When the musical number begins he has the greatest look of "-_-" on his face.
Once the song really starts going it switches to "Oh fine!"
During the Hook-handed thug's verse, we start seeing the other pub thugs bounce up and down to the song. Even a couple of rats are bogging to it, while a bewildered Pascal stares at them.
Anything Maximus does. Even the way he moves!
Maximus...with a sword. And of course Flynn's reaction while sword-fighting a horse with a frying pan:
Flynn: You should know that this is the strangest thing I've ever done! [Maximus knocks the pan out of his hand, they watch it fall into the ravine. Max's ear twitches as it hits the bottom] ...how 'bout two outta three? [Maximus holds the sword at his neck and he quickly holds his hands up]
Maximus eating a poster of Flynn like a paper shredder with the best expression ever.
Him parting the thugs in The Snuggly Duckling is a split-second of hilarity.
A moment earlier: Maximus does not recognize Flynn's face on the poster until he covers the nose.
Upon hearing a noise, Maximus leaps behind a rock and pulls down an overhanging tree branch to conceal himself... except that the rock and tree branch combine to look exactly like a horse.
After Gothel encounters Maximus and freaks out over a palace guard horse being so close to her hideout — and the implications for her and Rapunzel that means — there's a shot after she runs off of Maximus, head cocked to the side, with a perfect "WTF was that all about?" expression on his face.
Not to mention the reaction Maximus gives just as he is eating the apples Flynn gave him and comments "I paid for them... most of them."
The second he says "most of them" Maximus just kinda stops and stares down at the apples until the camera leaves him.
And the beautiful, beautiful, perfectly delivered sucker-punch (sucker-kick?) he gives Flynn immediately after agreeing to a truce.
Shortly after, while Rapunzel's distracted by being in a city for the first time, Flynn crumples up one of his wanted posters, Maximus catches him doing it (and after having it shoved in his mouth, spits it back out to plaster right over Flynn's real face), and the whole thing devolves into a childish shoving match. All that was needed was "I'm not touching youuuuuuuu!"
Then they get distracted by Pascal, who's giving them a look/gesture that clearly says 'Behave you two'. Flynn and Maximus stiffly let go of each other, both with -_- expressions... and they still take the time to get in one last hit on each other, not moving a muscle otherwise.
The entire sequence of Rapunzel trying to stuff Flynn into her closet. Just...all of it.
It's even better when you realize there is absolutely no dialogue going on since she hits him with the pan.
The scene where she stares at him (doing a standing thinker pose, no less) while he's upside down, hands and feet extended like some kind of art nouveau sculpture takes the cake.
Pascal's hilarious facial expressions throughout the entire Rapunzel-healing-Flynn's-hand moment.
Especially when Flynn looks at him the second time and Pascal just nods like "Oh yeah, that's the good stuff".
And Flynn's reaction—"You're being very cryptic as you wrap your magic hair around my injured hand."
Rapunzel's very first meeting with Flynn. There's something incredibly funny about the way she first brains him with a frying pan and then squeaks in terror and runs and hides.
Rapunzel hitting Flynn with the frying pan when he awakens the first time and the scene following it as she tries to get him in the closet.
Then hiding the satchel from him, and telling him he'll never find it. Flynn looks to the right, then to the left, and says, "It's in that pot, isn't it?"
[pause] ...*CLANG* Rapunzel: [after Flynn awakens again] Now it's hidden where you'll never find it!
A Freeze-Frame Bonus in that immediately after he points to the pot, the scene swamps out to the view of the tower, and snaps to black just as the CLANG is heard.
Pretty much the whole scene where Rapunzel has Flynn tied up in her hair, and interrogates him:
Rapunzel:Something brought you here, Flynn Rider. Call it what you will: fate, destiny... Flynn: [deadpan] A horse. Rapunzel: ...so I have made the decision to trust you. Flynn: A horrible decision, really.
Flynn trying (and failing) to use "the smolder" on Rapunzel. "You broke my smolder..."
Rapunzel's adorable reaction over her reaction of getting scared over a cute little bunny rabbit.
Flynn's obviously "full of bullshit" dialogue as he's clearly trying to trick Rapunzel is made of hilarity.
Ulf the mime thug, and the palace guards' bewildered reactions to his performance.
And his "Oh my!" look to the camera after Vladimir body-checks all of the guards.
The disturbed looks on the citizen's faces when he performs at the end.
"And this guy... I assume he's happy. He's never told me otherwise."
The whole scene where the pub thugs sing "I've Got A Dream". Especially when Flynn tries to resist singing along.
And pretty much everything Flynn says just before.
Flynn: You smell that? Take a deep breath through the nose. [inhales] Really let that seep in. What are you getting? Because to me, that's part man-smell, and the other part is really bad man-smell. I don't know why, but overall it just smells like the color brown. Your thoughts?
The nonchalant way that Vladimir (the big guy) just hangs Flynn like a coat before hook-hand starts approaching Rapunzel (to start the song).
"Head down." "Arms in." "Arms in." "Knees apart..." "Knees apa-Wait, why do I need to keep my knees apAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA!"
After Flynn goes flying, the thug looks up and watches him with a look of wonder. Blink and you'll miss it.
In the song "Mother Knows Best", Mother Gothel warns Rapunzel about all of the scary things in the outside world, including men with fangs. After Rapunzel knocks out Flynn, one of the first things she does is check his teeth.
Blink and you'll miss it, but in that song, watch for Gothel pretending to sauté a doll on the word "cannibals".
Rapunzel trying to hide in a mound of her own hair.
After Rapunzel knocks Flynn out and ties him to a chair, Pascal climbs onto his shoulder and attempts to wake him up so they can question him...by slapping Flynn in the face with his tail. Then poking him with it. And when that fails? He gives Flynn a "wet willy" with his tongue.
Happens again moments later, and it gets funnier the second time around.
One moment in "When Will My Life Begin" at the line where Rapunzel is talking about ballet. She's dancing...then twirls enough that she ties herself up and falls to the floor with a squeal. Basically, a lot of stuff in that song, including Rapunzel practicing ventriloquy...with Pascal, she's made a truckload of candles, and then there's her scaring Pascal with a papier mache mask as well as her standing on a stool, brush and paintboard in hand, staring at the walls of the tower trying to find some place with a free space to paint on, the accompanying line in the song being "There must be room somewhere!".
After stuffing Flynn in her own closet:
Rapunzel: I've got a person in my closet! Too weak to handle myself, huh mother? (chuckles and twirls her frying pan) Tell that to my frying pa- (accidentally whacks herself in the head with it)
Pascal's quick raspberry-blowing after Rapunzel says they can't go outside at the beginning.
A blink-and-you'll-miss-it moment. When the royal guard has chased Flynn and Rapunzel into a dam, which then breaks, sending water everywhere. As the wave is about to hit them, the guards all look ready to void themselves, but Maximus is staring it down with a look that just screams, "Bring it on, Bitch!"
Not long after the above, just after Flynn and Rapunzel escape the cave-in and flood:
Flynn: (Referring to Pascal) Why is he smiling at me?
This part here:
[the Stabbington Brothers show up] Rapunzel: Who is that? Flynn: They don't like me. [the palace guards show up] Rapunzel: Who is that? Flynn: They don't like me either. [Maximus shows up] Rapunzel: Who is that!? Flynn: Let's just assume for the moment that everyone in here doesn't like me.
Pascal and Flynn's expressions during the "I've Got A Dream" song.
The four little sisters when Flynn shows them the sheer bounty of Rapunzel's hair, just waiting to be plaited. Their expressions of joy are identical.
Then there's Max's grinning at Flynn as he's checking out Rapunzel's newly plaited hair. And the very embarrassed look on Flynn's face when he shoves him away.
Flynn waking up to find a very pissed off Maximus staring down at him.
Flynn: [smugly] Well, I hope you're here to apologize.
"And Vladimir collects ceramic unicorns" (big guy Vladimir clinks the ceramic unicorns together and cracks a grin)
In the bar fight when the hoodlums are trying to capture Flynn so they can claim the reward, and Rapunzel's trying to stop them. At one point she yells "Ruffians!" like that's their job description or something.
After Rapunzel has shoved Flynn in her closet and Gothel has returned:
Gothel: I've got a big surprise! Rapunzel: [nervously] Um, I do too! Gothel: Ooh, I bet my surprise is bigger! Rapunzel: [to herself] I seriously doubt it...
Rapunzel tries many ways of guessing what the crown is for, Pascal shaking his head at each try. When she puts it on her head, Pascal stares at her as if to say something exciting...before shaking his head a third time.
Tangled Ever After
Eugene's thoughts on his marriage day:
Eugene: This is the story of the day my life ended.
Eugene: "Everyone dying to catch a glimpse of me... US! I meant us."
Later on, Maximus ends up running into the above banner showing Eugene and Rapunzel, causing it to fold and make his nose even bigger.
The accordion player from the bar is on call for the wedding music... and is spurred into action the exact same way as before.
Eugene's "Whoa!" after seeing Rapunzel in her wedding gown... Coming immediately after the priest has that same reaction, then the short guy follows suit and Eugene shoves him off.
Right after Max and Pascal lose the rings:
Queen: Those were my grandmother's wedding rings! Hysterical Soldier: THE KINGDOM IS LOST! [castle explodes]
This is an Imagine Spot, in case the absurdity of it is confusing.
Three words: commemorative frying pans.
When Max and Pascal show up in time with the rings, they are covered in tar, and Max is wearing a dress, hat, and shoes. The King and Queen's expressions and Rapunzel and Eugene staring at them all confused as they put on each other's rings are priceless.
Better yet, Max proudly walks down the aisle.
After Rapunzel and Eugene kiss:
Shorty: HAPPY BIRTHDAY!
The Stabbington brothers are at the wedding, still chained up, wiping tears of joy.
Surpassed by the look of absolute bewilderment given them by the guard assigned to them.
Could also count as a Crowning Moment of Heartwarming, since the brothers were not only invited to the wedding by Rapunzel and Eugene, but also seemed genuinely happy for them finally getting married.
At the very end when Maximus accidentally bumps the wedding cake, and it rolls out the door:
Eugene: So, who wants a piece of cake? [Max and Pascal look on with Oh, Crap expressions]