The beginning of "She's a Super Sneak" When Robbie has the fish. Especially when the fish is staring Jackson right in the face.
One of the funniest moments occurs when Miley is considering sharing her secret, and Robbie Ray tells her that he trusts she'll do the right thing and she immediately tells him 'I'm fourteen, I'm almost guaranteed to screw this up'.
In an early episode where Hannah blows off the Queen of England to go to Jackson's volleyball game, and the confused queen asks her majordomo "Simon, have we been Punked?", the sheer incongruity of having the Queen of fricking England not only know what being Punked is, but thinking it might have happened to her was hilarious.
In the episode with Gilbert Gottried, Jackson is flipping through the channels and at one point you hear the Hannah Montana theme song starting from their television set. Jackson sighs in exasperation and yells "WHEN IS THIS NOT ON?"
How can anyone not laugh at Jackson's attempt to fool the Gottfried character with a Paper-Thin Disguise of Ozzy Osbourne. This exchange makes it more humorous.
Critic: I just have one question. (Removes Jackson's wig) How stupid do you think I am!? Jackson runs Jackson: SHARRON!!!
Before that, we have the following exchange:
Jackson: Listen...uh, listen...uh, liste— Critic: I'M LISTENING! (Beat) Jackson: Well? Critic: YOU DIDN'T SAY ANYTHING!
In the episode "Sleepwalk This Way", the beginning of the episode. The expressions on their faces are priceless.
During the fourth season, at the end of one episode, Miley and Lily decide to move their room to the barn. The reason for it? Jackson is eating a chili-dog and he walks to their doorway, burps into the room and promptly leaves. It was hilarious in a farce-like manner.
Some of Rico and Jackson's songs in the He Could Be The One episode are hilarious. What comes to mind is one where they're singing about boys doing stuff wrong (or something along those lines), and end with "We don't even know how to end this song". They then pause, look at each other, then look back to the screen and sing "la la la la" while they dance out.
They bring Siena with them for "I'll Always Remember You". The jazz song is the funniest including Siena telling Jackson. who thought he and Rico were going to be more than backup singers, that she had a better agent and Rico saying if Miley leaves they'll have no ride...leading them to run after her.
From 'Bye-Bye Ball:'
Jackson:(speaking in German accent) You vill tell me vat I vant to know. Ze choice is whether you will tell me before ze pain...OR AFTER! NOW WHERE IS ZE BALL?!
Oliver: Uh, what ball?(turns to Lilly and gives a thumbs-up, but she hits him in the arm)
Jackson:(speaking normally) The Joey Vitolo my dad gave me for my thirteenth birthday! (back to speaking in German accent) ZAT BALL!
Lilly: I don't know what you're talking about!
Jackson: Fine. Perhaps a trip to ze closet vill jog your memory.
Oliver:(as Jackson opens the closet) It's okay. It's just a closet. WHAT IS THAT?!(Jackson shoves him into the closet and closes it) No, no, no! (pause) Help me. (Jackson opens the closet.) She's at...Vitolo's. (collapses)
One episode features Miley accidentally blowing her secret by bragging to a TV star that she's Hannah Montana. In order to save her from being hounded by paparazzi, she (and her family) pretend to be lunatics who only think they're celebrities. This is funny enough, but it becomes hilarious when
Robbie Ray: (Wearing a over-the-top mullet wig) Hi, I'm Billy Ray Cyrus!
In "We Are Family: Now Get Me Some Water", the beginning. Miley is practicing for an awards show, while Jackson is playing a crazy car video game.
Jackson: You'll never take me alive, coppers eh!
*Miley tries to get back to playing*
Jackson: Outta me way, Grandma! Got the popo on my tail.
Miley: Jackson, I'm trying to practice for the awards show.
Jackson: Yeah, don't worry. You're not bothering me.
Miley: But you're bothering me.
Jackson: Oh, right. Don't care. Look out cow! *crashing and mooing can be heard* Oooh, look at that heifer fly, right into the marching band.
*Miley gets up from the piano to watch*
Miley: You know Jackson, you have a real car. Here's a thought: get in it and drive away!
Jackson: Yeah, I would but that takes real gas which costs real money, which Rico doesn't pay me a real lot.
Miley: Why don't you just ask Rico for a raise?
Jackson: (in cartoony voice) Ask for a raise. Gee that sounds like a good idea. Oh wait. I did.