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In general, the idea of celebrities dressed as pimped up animals, monsters, aliens and even food can get a few chuckles…

Due to being a moments page, no spoilers have been marked. You have been warned.

General

  • A good majority of Ken's guesses, especially in later seasons when the crowd begins outright booing him.
  • Any time a Masked Singer needs help taking their head off.
  • Sometimes, the singers themselves will visibly react to the judges' guess which often time leads to them looking almost offended by said guesses.

Season 1

  • The constant gag of the Deer accidentally hitting Nick with his antlers!
  • Throughout the show, Rabbit can be seen keeping in character with his head twitch…
    • After winning his song battle in his debut episode, he proceeds to bunny hop backstage!
    • After performing "Poison", he admits to being very tired and proceeds to comically fall on the stage.
  • When one of the judges asks Unicorn if she was a gymnast, she responds “in the bedroom”.
  • The addition of guest panelist JB Smoove for episode 7 led to several of these:
    • First off, his habit of standing up every time he had to say something - probably just being polite, but after a while Ken found it annoying.
      Smoove: (while Ken is shoving him back down) I have solved a lot of mysteries like this. Who shot Ray-Ray…
      (Lion drops to her haunches laughing)
    • Describing the Lion and Nick Cannon, who's in a shiny suit with a texture like a Christmas cracker, as "the snazziest prom couple I have ever seen".
    • His words to the Bee:
      Smoove: Nobody's grandma does this all day. (mimics her shimmy) […] And just for my own purposes, I'ma let my wife know if they make that costume in her size - Is there a stinger on the back of that bad boy?
    • One guess as to the Rabbit's identity: Billy Ray Cyrus.
      Nick: Miley's daddy can't move like that no more. He gon' achy-break something.
      Smoove: (laughing) That was a good one, Nick…
      Ken: No it wasn't a good one! (at Nick) C'mon, Not-Steve Harvey! C'mon! (massive audience reaction)
  • There's a couple during Monster's unmasking.
    • During the 'Take It Off!' section, Jenny starts shaking Ken back and forth while hysterically screaming 'WHO'S THE MONSTER?!'
    • The utterly incredulous reactions from the judges when Monster is revealed to be T-Pain. Jenny is practically in a tizzy, given her super loud, enthusiastic shriek.
      Kenan: T-PAIN?!
      Jenny: EEEEEEEEH!!! NO WAY!!!
      Ken: Are you kidding me?! T-Pain!
      • Made even better when Nick starts laughing, and T-Pain does a little jig!
    • During the guessing, Jenny suggests Michael Vick, of all people. Everyone else's "WTF" reactions are priceless, but Monster gives a little start and looks at Jenny like he's outright offended by her guess, before doing what can best be described as an "Are you kidding me?!" gesture.
    • During Monster's otherwise tearjerking, show-stopping performance of "Stay With Me," one hilarious detail many have noticed is that his fur was neatly combed out this time - complete with a sharp little side-part.

Season 2

  • Some backstage shenanigans when the Egg approaches the Butterfly with a net, only to back off when she brandishes a Frying Pan of Doom.
  • Speaking of the Butterfly, she has a habit of hitting Nick with her antennae, much like Terry Bradshaw did one season before.
  • During Ice Cream's performance in the smackdown against Ladybug, Ken ends up getting playfully smacked by the female judges!
    • Ice Cream's song in said smackdown just happened to be Whip It!!
    • Extra points for being smacked on the "Whip it good" line!
  • During Ladybug's solo during her smackdown with Ice Cream, Ice Cream simply sits down and playfully rocks back and forth a little…
  • During one guessing round for the Penguin, Nick says that if it was Sherri Shepherd, she would've grabbed his butt by now. Guess what the Penguin does next.
    • Bonus points: she actually is Sherri Shepherd.
  • The Leopard in general is a riot, as he takes the over-the-top nature of his costume - a leopard in a big, poofy, fancy, over-the-top Elizabethan-style gown - and rolls with it, creating a flamboyant, dramatic, Large Ham diva of a character that he keeps with the whole time. He even goes as far as to make cat-pawing gestures, sashay around with as much flamboyance as he can muster, and emphasize his Rs to sound like purring!
    • Later on, the Leopard physically flirts with Nick, including grabbing his butt. He even proposes to Nick in one episode.
    • The Leopard also claims that he and Nick have gotten married in between episodes, which Nick happily confirms.
    • The Leopard says in one clue package that he's tired of hearing about his famous ex. Jenny comments that he and Nick have that in common.
      Leopard: We don't need to talk about her
  • Special guest Triumph the Insult Comic Dog started out promising to be on his best behavior, which doesn't mean he can't be funny:
    "How can I say anything bad about Nick Cannon? He's the biggest thing in showbiz ever since Ryan Seacrest started saying no to things."
    (to Tree) "You look like the last thing Elton John sees before the Ambien kicks in…"
    • On putting Ken Jeong in his place:
      "I know Dr. Ken was put here to ensure there's no sexual chemistry between anybody…"
    • In the hunt for Fox's identity, Triumph posits that the costume could be a clue to where he works at, namely Fox. Initially everyone seems to agree with his logic…until he posits it's Lou Dobbs, aka the Business Anchorman for Fox News, saying he was in a boy band in the 80's.
    • Of course with him being a Rottweiler and having a contestant dressed as one, there was bound to be hilarity with what Triumph would have to say, specifically saying he was the father, having walked out on Rottweiler's mom. This naturally causes Rottie to fall to his knees in despair. Triumph's defence? :
  • Ken once again fails to smoke out a singer is a former acting partner, when the Tree is unmasked as his A Christmas Story Live! co-star Ana Gasteyer.
  • One clue package shows the Thingamajig marrying himself, a la Dennis Rodman. Nicole snarks, "Oh, so he's a narcissist, just like all my other exes." Cue Nick giving her an indignant look from the stage… as a picture pops up, revealing the two used to date!
  • When the Southern Belle Ladybug is revealed to be the very British Kelly Osborne, she reveals she realized her English accent would be a dead giveaway mere seconds before going onstage. She panicked, and put on the Southern drawl on the fly… and then realized she'd have to do that the whole time. To her credit, it actually worked. No one guessed who she was!
  • After the Black Widow is unmasked, she confirms that she did injure herself briefly after the first performance.
    Black Widow: Don't ride a hoverboard at thirty-three.
  • Week 10’s guest judge T-Pain, season 1 champ The Monster, after seeing this season’s fuzzy monster Thingamajig perform:
    T-Pain: Hello, son.
    • The Fox uses the opportunity to perform "Blame It". The Road to the Finals recap has to resort to String Theory to explain this move:
      Nick Cannon: So check it out. Fox, on FOX, singing a Jamie Foxx song, whom the panel thinks Fox might be, a song that featured T-Pain, in front of T-Pain, a.k.a. Monster, whom the panel also thought was Jamie Foxx, and who won the Golden Mask, which Fox is now trying to do. Got it?
  • During Thingamajig's solo during his Smackdown against Butterfly, he can be seen playfully shaking his butt at Butterfly!
    • And a quick blink and you'll miss it moment: during said wiggle, Butterfly attempts to literally kick his butt.
  • Ken guesses the Leopard is Jeff Goldblum.
    The Leopard: Kenneth, Kenneth, Kenneth; if you were any colder, you'd be in Alaska, darling.
  • During "Road to the Finals," we get some time with those who have already been eliminated.
    • When discussing how absurdly tight the security for the show is, Johnny Weir chooses to complain about… being forced to wear tube socks.
      Weir: Do I look like someone who wears tube socks?
    • It's revealed that Nicole crashed the goodbye interview for her "future husband" the Thingamajig, aka, Victor Oladipo… oh, and Ken was there, too. Oladipo serenading Nicole on the spot is a sweet moment that turns hilarious when Ken glomps him.
      Oladipo: … Was that planned?
    • The truly groan-worthy explanation behind one of the Leopard's clues. He showed a picture of four grandmas because Seal has four Grammys!
  • Jenny, just before locking in her guess for the Fox:
    Jenny: Oh my God, I agree with Ken. In the finale. I must have a fever.
    • Even better? They're wrong.

Season 3

  • The first guest judge is Jamie Foxx, whose name has been brought up a lot as a possible contestant in the first 2 seasons - which is why Jamie starts complaining about how this show has apparently ruined his life.
    Jamie: One night my momma came into my bedroom, she said "I got $200 riding on this…"
    • While Jamie's musical experience lets him give relevant critique, he also goes one step further and reads the body language.
      Jamie: I knew she was a queen when she walked out. Lemme give it to you… (stands up) She was all, "where's my mark"… "put me where I'm needed", and "don't have me in this too long". (campy hand-clutch gesture) Don't. Have. Me. In. This. Too. Long. Dolly Parton (even more campy snapping and clapping) does not do this.
  • The show delighting the crowd with a clip Robin's 2003 debut album, and long haired, goatee sporting, only going by 'Thicke' at the time Robin.
  • The very first unmasking of season 3 is Lil Wayne as the Robot, which triggers a ginormous reaction from everyone - Robin Thicke just storms out of frame for a moment, Ken Jeong is kneeling on top of the panel, while Nicole Scherzinger is frozen still.
    • The reactions are well-deserved and not just because of Wayne's A-list status. Robin, Nicole and Jamie previously recorded with him (five times, in Robin's case). As Jenny aptly put it…
    Jenny: You just Ken Jeonged yourself.
  • White Tiger pretty much outed himself as one of the non-singers when he ran out of breath mid-performance in episode 2. It leads to Robin saying "you could mute the music and it would still be entertaining" before the entire panel melts down uncontrollably.
  • When Llama claims to have been around "firing cannons", Robin is the first to joke about firing Nick Cannon.
  • White Tiger opens up his third clue package thus:
    White Tiger: Look who's still here! Shocked? Me too!
  • Just before Frog's first clue package ends, a fly appears during the Iris Out. Frog manages to catch the fly with his tongue about a split-second before the package ends.
  • The Elephant's incredibly fake British accent during his take on "Friday I'm In Love". Especially when he's revealed in the same episode as the very American Tony Hawk.
  • With the famously food-loving Gabriel Iglesias for a guest and two Anthropomorphic Food singers still here, you have to expect the jokes to take a certain direction.
  • The guest judges are introduced wearing masks. T-Pain's "mask"? A tiny plush of the Monster that is smaller than his head. He doesn't even have a way to wear it. He just holds it in front of his head.
  • Taco and Banana hugging after the Group Number is considered both Heartwarming and also funny at the same time, even Ken made a remark on it.
  • Jenny's Ken Jeong impression, complete with giant head cutout.
    Ken: You know what? It is obvious after that I have no friends. You know what I mean? Like…
    Nick: Duh-doy.
  • While guessing Taco's identity, Jenny suggests Jerry Springer. As is the case for the TV broadcasts, a face of the guess goes over the mask. Ken then suggests throwing a chair at him to see how he'll react. Funny on its own, but the editors had a bit of fun with this by replacing the initial Jerry Springer face with an Oh, Crap! face of his.
  • In a bit of an inverse of the Running Gag from the past two seasons, none of the panel recognize Tom Bergeron as the Taco despite him having previously worked with all of them except Ken.
  • The sheer spectacle of Sarah Palin singing "Baby Got Back".
    • And the reactions when she's unmasked are noteworthy too. Nick yells 'OH MY GOD' as soon as he sees who's under the mask, the audience goes wild, Robin lets out a 'Holy snap!', and all the other judges are shocked into silence.
  • Swan managing to get Ken to blush after enthusiastically declaring her love for him at the end of her performance of "I Hate Myself For Lovin' You".
    Ken: "I hate myself for lov-", wow, who are you? My wife?
  • Yet again, Ken can't identify one of his former co-stars when the Swan is revealed to be his The Duff co-star Bella Thorne.
    Jenny: That's classic Ken Jeong, never guessing his co-stars for it. This is another Margaret Cho moment.
  • Will Arnett's guess for the Rhino: Will Arnett.
    Nick: Can you sing like this?
    Will: I don't know. Maybe I can.
  • Ken's Humiliation Conga isn't nearly over, when he deliberately goes against Jenny's final guess. She's the one who nailed it this week.
  • The April Fools episode, naturally, is rife with these moments:
    • Nick fooling everyone into believing that Snoop Dogg would be a guest judge—when it was actually Nick's friend in reality.
    • Nick and the panel make fun about how Ken is about half the size of White Tiger, to the point of getting an actual size cardboard cutout of the judge!
    • Frog gives Kitty a Valentine cheering for the best singer of Group B—Frog himself. Naturally, Kitty was not amused. Now crosses into Hilarious in Hindsight, when Kitty was eliminated before Frog, making him the last member of Group B.
    • One of Banana's clues was that he survived a traumatic event in his life. Robin deduces it's Billy Ray Cyrus, positing that the traumatic event was watching his… interesting VMA Performance with Billy's daughter.
    • How does Astronaut end an episode airing on April Fools Day? By rickrolling everyone, obviously!
    • For one last prank, Nick tricks everyone into believing Banana was eliminated, before revealing that he's safe, before revealing that, mercifully, White Tiger is finally out.
  • The sight of guest judge Yvette Nicole Brown taking off her hoop earrings has Nick suddenly get all jittery.
  • Ken makes a pun that'll probably keep him sleeping on the couch for a week:
    Ken: I know that pimpin' ain't easy, because I married a Ho.
    (audience gasps in horror)
    Ken: What? That's my wife's maiden name.
  • The Cold Open of the Battle of the Sixes have the contestants in a group therapy meeting (with the therapist being Dr. Drew Pinsky reprising his role as the Eagle from the previous season) about issues their masked outfits are giving them in "real life". Turtle gripes that his shell, hairdo, and leather jacket all together being covered in spikes means he can't get close to waterbeds, bubbles or balloons. Cue the Frog coming up to him and popping a balloon on Turtle's head.
  • After a performance, the judges ask The Turtle what's it like inside the costume. Turtle's response:
    Turtle: (laughing) It's hot! It's really hot. And it's heavy!
  • The guest judge for the top 6 round was Gordon Ramsay, leading to all the singers delivering food-based clues. True to form, Ramsay actually snapped at Nick for bringing his bare hands too close to a chocolate cake. It's all in good humor of course, just as Ramsay managed to get the panel and the audience behind him in goading Nick to eat one of the dishes brought out - fried crickets.
  • The physical clues for the Quarterfinals are all in delivery boxes, and one in particular is so huge it needs to be wheeled out, prompting Jenny to ask "is that a dead body?" It's a prop zombie, but close enough.
  • Guest panelist Jay Pharoah is so awestruck upon hearing Night Angel that he literally Screams Like a Little Girl. When Frog closes off the episode, he does it again.
  • Ken challenging the hottest guess for Frog to date leads to him teeing up Nick for an Armor-Piercing Response:
    Ken: It might be Lil Fizz…
    Nick: You know who Lil Fizz is?!
    Ken: I know… Hold on! WHOA! Are you doubting me that I don't… He is a family friend!… He dropped me off here, man! We carpool to work! He's out there, rehearsing for the millennial…
    Nick: If he's out there then who's this?!
  • In the Semifinals, Ken gleefully running around with his arms triumphantly raised after he finally makes a correct guess with the Rhino… including running onto the stage to hug an unmasked Barry Zito.
    Nick: This is not The Price is Right!
  • The fact that Taco's microphone is a hot sauce bottle.

Season 4

  • It's Episode 1 and already Ken is making wild guesses, but none flabbergast the others more than his guess for Popcorn: Carole Baskin. Nobody buys it, with Popcorn clearly unimpressed even with her goofy grin.
  • With Giraffe, Ken makes his guess of Garth Brooks but explains too much to the point that Giraffe gets bored and sits down, as if on the verge of napping. Even better (or worse at least for Ken) is that the editors don't even bother putting Garth's face over Giraffe's head as they usually do with other guesses, nor do they include him with the other guesses made in the transition.
  • While Dragon performs "Mama Said Knock You Out", Nick takes it almost too literally and while dancing along, slaps one of the men in black dancing with him but continues as if nothing happened.
    • Speaking of the Dragon, Jenny's first impression guess was Adrian Peterson. Jenny, knowing that it's wrong, hides under the table in shame.
  • The sheer insanity of the closing moments of episode 2. After stumbling through a rendition of "Stand By Me", Gremlin just decides he's done playing, unmasks himself as Mickey Rourke and goes home.
    Nick: We’ve lost control, it’s The Gremlin Show!
  • Episode 3 begins with Nick introducing a new contestant, The Robin. Not the bird mind you, Robin Thicke. The mask itself is just Thicke's face on a paper mask, worn by guest judge Joel McHale, who then proceeds to insult Ken and sing "Blurred Lines" but is cut off before he can finish.
  • Once again Ken manages to annoy Giraffe by over-explaining his guess, but he also ends up annoying the entire judging panel. Giraffe requests a stool to sit on and a cup of tea before just outright napping on the ground, Jenny gets a neck pillow, Nicole naps on the desk, and Robin plays with the Robin Thicke mask Joel had on earlier. His rambling even goes into commercial, and upon returning he's still talking!
  • While they're basically more grounded than the rest of their group, The Snow Owls responding to one of the Twitter questions, which is basically asking if Ken ever guessed them on the show is priceless.
    Lady Owl: I'm defiantly not Bjork and I'm not Honey Boo-Boo.
    Sir Owl: I'm not Fabio, I'm not Jag, I've never been on Jag I mean...Jaaaaaaag?
  • Speaking of Robin and Giraffe, the former once again gets a Ken-like moment of failing to guess someone he's close to when the latter is revealed as childhood friend, former bandmate, and neighbor Brian Austin Green. Upon realizing its him under the mask, Robin simply does a Face Palm and walks away from the table.
  • Mushroom being able to hold the longest note in series history leaves Nicole frozen still again.
  • When Baby Alien gets eliminated, the crowd begins the typical "Take it off!" chants, but one problem- the costume has no arms, so Nick asks, "How do you take it off?" to which Ken replies, "I don’t know!" Eventually, the Men in Black come onto the stage to remove the costume and reveal Baby Alien to be New York Jets QB Mark Sanchez.
  • Lips's performance of "Native New Yorker". She audibly struggles to contain her laughter while singing the song, even snorting at one point while giggling. And while most of the song is sung quite off-key, it's clear she's had plenty of fun performing.
  • Speaking of the Lips, Ken's first impression guess for her: Mariah Carey.
  • For this season, the panelists write down their initial guesses for the contestants. What did Nicole write down for the Squiggly Monster? One of the Ying Yang Twins! Not the name of one of them; that phrase exactly.
    • This moment is one-upped by Nicole's first impression guess for Whatchamacallit… Uncle Itt.
  • Just before Whatchamacallit unmasks himself, Nick questions if the judges' final guesses were "Ken Jeong wrong". No less than thirty seconds later, Whatchamacallit is revealed to be Lonzo Ball—which not only happens to be Ken's final guess, he's the only one to get it right!
  • After Crocodile delivers a deliberately downbeat but still impressive performance fully intended as his "Someone You Loved", the panelists comment on how hard it would be for the incredibly flamboyant Crocodile to attempt this sort of thing, and end up goading him into catwalking up and down the stage - whereupon his tail whacks Nick by accident.
  • The return of Jay Pharoah pretty much guarantees at least one funny moment.
    • After Robin posits that Mushroom is actually Jaden Smith, Jay disputes it, in the voice of Jaden's own father.
  • During the smackdown between Broccoli and Mushroom, Broccoli gets so close to Mushroom's face that Ken calls out, "Social distancing!"
  • Jellyfish reveals that her personal connection with one of the judges is with Ken, which leads to some beautiful Mood Whiplash later on - she's revealed to be Chloe Kim, and anyone would think it's because they're both Korean-American (and Ken does state that she was an inspiration to him and his children), but it's actually because she was inspired by his old videos about answering medical questions to send him a DM - which he never replied to and likely never even noticed. For TWO YEARS.
  • First-time guest panelist Craig Robinson is simultaneously awed by the top 6's performances and reduced to a ball of nerves once it's time to guess who it is, going with the majority vote each time (and when there wasn't one, he just went with Ken's reasoning). He ends up getting all 3.
  • Nick holding all the unvaulted First Impression guesses allowed him to set up a golden moment where each panelist somehow changed their mind and still hit upon someone else's first guess for the Crocodile.
  • This season's Road to the Finals reveals that Bob Saget was totally unaware that Squiggly Monster wore a nice hat until he saw the head backstage after his unmasking.
  • Crocodile, unmasked as Backstreet Boys member Nick Carter, taking slight offense at Robin assuming he was another member of the band.
    Nick: (laughing, incredulous) Howie D!?

Season 5

  • Raccoon turned out to be just as… entertaining… as White Tiger, leaving Robin in a full-on Head Desk by the time he's done.
  • The Snail is unmasked… and much to everyone's surprise, nobody comes out at first… until it's revealed to be "Movie Star, Oscar-winner, and A-List Amphibian" Kermit the Frog.
    • Something about Kermit the Frog singing "You Make My Dreams Come True" by Hall & Oates is equal parts adorable and hilarious.
    • Upon being unmasked, Kermit remarks that he's never going to stop hearing this from Miss Piggy. What makes this funnier is that this can interpreted as either the fact that he got unmasked early in the show, the fact that he got to perform on the show before her or both.
  • An Epic Fail moment comes from Ken, who correctly guesses Phoenix's identity as Caitlyn Jenner... but then changes his guess before the unmasking. Needless to say, once Caitlyn reveals herself, Ken is left lying on the desk feeling stupid.
    Caitlyn: Ken, you have always been an idiot! What are we gonna do with you?
  • Raccoon's unmasking begins... with him trying to take off his pants. Thankfully, a Man in Black sets him straight, leading to his actual unmasking.
  • Every time Ken and Joel started dancing to one of the Masked Singers' performances.
  • Who was Jenny's first impression guess for Grandpa Monster? Morgan Freeman. Even Niecy Nash sounded embarrassed to say it out loud, and the other judges found it unbelievable, especially coming from a supposed master guesser like her.
  • Speaking of Grandpa Monster, Nicole guessed Jake Paul, but turns out she got the wrong Paul brother as it was Jake's big brother Logan underneath the mask. Much like Caitlyn Jenner to Ken, Logan couldn't help but call her out on it.
    Logan: You thought I was Jake?
  • The Russian Dolls' third clue package has this zinger near the end.
    Russian Doll #2: High five. Oh, sorry. You don't have hands.
  • Bulldog's clue package is worth several laughs. It basically consists of him running around, terrorizing fellow contestants and judges alike.
  • The entire reveal of Bulldog is insanity not seen since Gremlin's self-elimination. First, Niecy Nash decides to nullify the audience and panel votes and chooses someone to eliminate, even having them unmask on the spot! That's crazy enough, but then the Bulldog is revealed to be none other than Nick Cannon! Yes, the host of the show competed his way back to hosting duties, and it must be seen to be believed.
  • The official return of Nick to full hosting duties is marked by an impromptu rendition of "That's What Friends Are For" by the panelists - the stark contrast between the voice of Nicole, who's been a legit recording artist, and the... voice of Ken makes some lovely Mood Whiplash (especially when Jenny tries to silence him with a sponge ball gun!)
  • Robin is the first one to notice the irony of both the sea creatures, Crab and Seashell, being booted in the same night.
  • The Recap Episode which doubled as The Maskies had some interesting awards, including:
  • The Spicy Six coincides with Cinco de Mayo, and Robin decides to conduct his own "peaceful protest" of Cluedle-Doo's random intrusions by tucking into a bucket of fried chicken during the show.
  • Anytime The Piglet starts twerking on stage after a performance.
  • When it came to the final guesses for the Russian Dolls before the unmasking, there were some funny guesses.
    Nick: Nicole, for The Russian Dolls, you guessed the entire cast of Glee!
    • The judges cheerfully shouting "twist it off!" as it was time for the Russian Dolls' unmasking.
    • When The Russian Dolls are being unmasked and Nick has trouble unmasking them, Robin yells, "Get a blowtorch!".
  • Following the reveal that Cluedle-doo is really Donnie Wahlberg, he and his wife Jenny McCarthy share a series of kisses. Robin tells them to "Get a mask!"
    Nick: You thought he was Akon!
  • Nicole's initial guess for the Chameleon was Nick Cannon, which later became hilarious when Nick Cannon himself read out the panel's First Impression guesses.
    Nick: This could be some amazing CGI right here.
  • Despite the shocker the previous week, Jenny turns the Awesome Ego all the way up in the finale, even "preparing" to be proven right for her final guess of the season by dolling up in an '80s Hair wig that's wider than her shoulders. The kicker after all that - it somehow works.

Season 6

  • When she's introduced, Jenny holds up both her Golden Ear trophies.
  • Inside the box where the judges put their First Impression guesses in the first episode, there is now a hand that grabs the clues. The reactions to it for the first time are priceless. Nicole, who encounters it before anyone else, actually scuttles away and sort of runs to Jenny for protection.
    • When everyone is putting in their guesses for Octopus, the hand makes friendly gestures with Robin, Ken and Nicole... and then tries to pull Jenny inside.
  • When Nick introduces the Take It Off Buzzer to the panel, he warns them not to use it willy-nilly. Cue Ken doing just that.
  • All of Hamster's antics onstage - including, among other things, pretending to pee on Nick. He also tells the camera, once he's offstage, that he hopes he gets to stick around and continue making Nick even more uncomfortable.
  • Episode 3 managed to have a bigger whammy than the actual reveal of Dalmatian - Nicole's first impression guess was "one of the Lil's" (she actually wrote that down as her guess), and Jenny guessed Steve Harvey. Dalmatian is hopping with disbelief and Nick outright tells Ken that for once, his guess isn't the worst.
  • Since episode 4 is themed around a house party, the judges all are dressed as if they were going to one... other then Ken, who didn't get the text message about it.
    • Even better? His subtitle is "Who Invited This Guy?"
  • The Baby's final performance before elimination? The theme song from The Flintstones. Yes, really. The entire audience is equal parts hysterical and making WTF faces, and Ken declares himself to be completely speechless "for perhaps the first time in my life."
  • Jenny is absolutely convinced that Baby is Bruce Willis, to the point where she puts on another 80's wig, just like she did when she made her correct guess on Piglet. It isn't - it's actually Larry the Cable Guy, who she had worked with before. Naturally, Larry is quick to call out the humiliated Jenny.
    Larry: When you came up with that wig on, I thought you knew! I thought "well, she's doing a trailer park girl", y'know? And everybody thought "here's Bruce Willis!" Boy, what a letdown, huh?
  • During their closing words in the Time Warp, both Bull and Skunk have a mishap with the time machine. Bull is sent to a medieval battlefield when trying to get to the finale, while Skunk is sent back to Season 3 where she gets to watch Bear get unmasked.
    Skunk: Someone needs to fix that time machine!
    • Also, the entire premise of the episode. Ken's attempts to cheat at the Golden Ear contest result in him building a time machine and it backfiring on him.
      Nick: Ken, what did I tell you about messing with the space time continuum?
  • After being unmasked as Hamster, Rob Schneider is impressed he made it so far. Why?
    Rob: You try competing with a bull who can do the splits.
    • Finally, as the show comes to a close, Rob belts out his famous line from The Waterboy: "You can do it, Masked Singer! All night long!"
  • Ken's use of the Take It Off Buzzer turns out to be a complete failure, proving that he really can never catch a break. As a result, Nick punishes him by demanding that he wash his cars.
    • Even worse for Ken? Nicole got Pepper's identity correct...as her First Impression guess.
  • Jenny hitting the Take It Off Buzzer was also a total failure, and Nick punishes her by making her clean Ken's dressing room (which Ken comments that he wouldn't wish that on anybody.)
  • Jenny is not taking being in last for the Golden Ear trophy very well, to the point where she tackles the Man in Black who brought it out.
  • The Reveal that both Jenny and Nicole had been cheating the system by putting down more than one name for their First Impression for Skunk. Laser-Guided Karma strikes eventually as Robin has the one correct guess this time.
  • In what can only be called a move worthy of Ken, Robin is the sole dissenter for Banana Split's identity and not only is he wrong and everyone else is right, Banana is David Foster, whom Robin knows personally!
    • Also, Robin's First Impression guess for who Banana was is "that other guy".
    • Robin points out how Ken recognized David's signature "conductor" hand motions while he was playing piano, to which David responds, "But I'm actually a really sh(HONK HONK) conductor."
    • Finally, after being unmasked, David still doesn’t bother to sing and just walks up to the panel to watch Katharine sing.
  • When it's pointed out that Ken actually has a chance to win the Golden Ear, everyone is shocked but Nick remarks that at least it hasn't gone to his head yet. Cue Ken walking out to music with sunglasses and a cape... at which point he is then one upped by Jenny, who comes out on roller blades with both of her trophies.
  • During the Finals episode, an unmasked Ice Cream of the Banana Split pair, Katharine McPhee, deadpan snarks that when she was on her star-making show American Idol she made it to second place and here she made it to third place, so she's been regressing in competitions.
  • When talking about all of the guesses the judges' have had for him, Bull takes the time to specifically mention that, no Ken, he is not Dwayne Johnson.
  • In the final First Impressions guesses, Ken has the chance to tie with Nicole for the Golden Ear. When Ken sticks with his final guess for Queen of Hearts, he confidently thinks he got it right. However, when Queen of Hearts is revealed to be Jewel, not only does he lose the trophy, but he's also the only judge to get her identity wrong.
  • During the Christmas Sing-Along, all the eliminated contestants get to sing "Rudolph the Red-Nosed Reindeer". All, that is, except Johnny Rotten (Jester), who has to be read some lines from a tablet. To put that in perspective, even David Foster, who never sang once during his run as part of Banana Split, sings this time.

Season 7

  • When all the teams are shown together, Jack in the Box noticeably never reacts to anything that goes on and simply remains in the box.
  • It quickly becomes clear that McTerrier can't actually see anything in his costume to the point where he runs into one of his back up dancers' wheelbarrows during his sole performance.
    • After being unmasked, Duff Goldman admits that he thought he was going to be sued when his mask fell off after his performance.
  • During the Group A performance, Cyclops tries to keep up with Thingamabob and Firefly's dance moves, but since his costume is so big, he sticks out like a sore thumb.
  • During Cyclops unmasking, Ken Jeong excitedly asks, "What are you looking at?!" when the cyclops eye keeps moving left and right.
    • Upon the unmasking, Cyclops quips "It's finally nice to see an audience." given his one eye.
    • Cyclops quips "look at these hands", followed by Jenny saying "Look at those feet!"
  • Ken's guesses in Episode 4 are so bad, the crowd literally begins chanting "No, Ken!" He takes it in stride, retorting, "How dare you?!" in what is clearly an amused voice. Then, when he turns out to be the only one to correctly guess the eliminated contestant, the chant hilariously turns into "Yes, Ken!"
  • During his performance of "I Fought The Law", Armadillo tries to do a high kick, but winds up losing his balance and falling flat on his back instead. The panel promptly bursts out laughing as the background dancers scramble to get Armadillo back on his feet. Ken all but collapses on the desk because he's laughing so hard.
  • Expecting Hydra to be three people? Nope. Instead, when it turns out to be Penn and Teller, Teller pushes a puppet of a rabbit in a hat through the middle head.
    • When it's time to actually unmask Hydra, Nick has no clue how to actually get the mask off, largely because Hydra's hands cannot reach any of his heads, which leads to the hilarious visual of everyone chanting while Nick looks around confused so he actually can take it off.
    • Even after being unmasked, Teller still keeps up the facade of never speaking publicly by holding a fan over his mouth when the duo gives their send-off performance.
  • How does Prince finish his first performance? By pieing the camera!
  • Baby Mammoth is so inspired by being on the show that she feels compelled to write a song... which is just the words "Baby Mammoth" chanted over and over in a rhythmic manner. The panelists and the audience 'sing' along enthusiastically.
  • Shaggy's true bombastic personally completely contrasting Space Bunny's much calmer one, with even the judges admitting how weird it is.
    • As Shaggy sings his encore, the panel starts a conga line and Nick is also trying to do one with Shaggy.
  • After Queen Cobra is unmasked as En Vogue, Nick takes the time to call out Ken for pronouncing their name wrong.
  • When the eliminated singers are singing their bonus number, Teller ducks under the camera and holds up the rabbit puppet so he can sing with everyone else.

National Tour

  • While the subplot itself is rather sweet, the sheer crackiness of Alien and Taco falling in love and outright getting married is worth a few chuckles.
  • On that topic, Alien's Bachelorette Party. To wit, Alien and a female audience member watch Big Mike, Thingamabob, and Robot all dance around them while they act as they are real male dancers.
  • After Baby finishes singing, rather than waiting his turn, Thingamabob steals the microphone out of his hand.

Season 8

  • The Knight quickly proves himself to be a comedic type, constantly bumping into Nick with his duck and quipping at the panel when they make bonkers guesses.
    • After being unmasked, William Shatner admits that he had an extremely hard time with moving around in his costume, especially with the visor restricting his view.
      William: It was terrible!
  • After the Hedgehog is revealed to be Eric Idle, he reveals that he needed the permission of Paul McCartney himself in order to perform "Love Me Do" on the show. Paul accepted on the condition that Eric tells him the show he's participating in—just so he wouldn't go on it.
  • Pi-Rat continues the trend of contestants struggling with their costumes by complaining about his lack of visibility, to the point where he wanders off the stage and Nick has to drag him back.
    Pi-Rat: I can't see s(BEEP)t!
    • When Nick informs Pi-Rat that Donny Osmond is on the panel, Pi-Rat quips "Oh wow you mean he's doing something without his sister?", which prompts Donny to come marching down to the stage in mock-anger, only for him to simply kiss Pi-Rat on the nose.
      • This leads to another funny moment later, when the panel is giving their final guesses for Pi-Rat. Donny says that he knows exactly who it is, "because I kissed him." And he is in fact the only panelist to correctly guess that it's Jeff Dunham!
  • When the panelists are locking in their final guesses for the Panther, Ken convinces Donny to have Andre Drummond of the Chicago Bulls be his final guess. It's only after Donny does so that Ken does a Bait-and-Switch and locks in Sam Richardson as his guess instead of Andre, laughing at the former Peacock's face as he does so.
  • Every time a contestant of tall stature appears on the show, the panelists usually say Montell Jordan as one of their guesses for the celebrity inside. Come the Panther's unmasking—which turns out to be Montell himself—and none of the panelists get him right, prompting them into Stunned Silence. To rub salt into the wound, it's Nick who manages to figure out his identity before the panelists!
  • Despite being a renowned playright responsible for some of the best musicals out there, Andrew Lloyd Webber proves that he fits in with a show like this by saying, "My mind's in a Maize".
  • Miss Piggy is naturally a riot during her time as a guest panelist, complete with somehow convincing herself that Robo Girl is her.
  • Nick comments on how the revealing of the Queen will be dynamite—and on a night involving the Muppets, he really should've known better, since this prompts Crazy Harry to set off an explosion backstage.
  • Hall Of Fame night is complete riot from start to finish. Highlights include:
    • Nick claiming that with Ken's absence, the crowd will have no one to boo.
    • Who takes Ken's place this episode? Leslie Jordan is announced as the substitute panelist - but is quickly followed by Joel McHale, who is only even there because he was looking for Ken. He actually suggests that the audience look under their chairs for him and adds that he might also be naked.
    • Both Robin and Joel using Ken's catchphrase, which causes the editors to paste his face onto theirs.
    • Everyone's shock by Bride turning out to be a harsh-sounding man Disguised in Drag.
    • The onstage clues are presented via the goat-as in an actual goat named Hawkeye.
    • Since Ken isn't present, the crowd decides to go extra hard on the other judges, leading to them booing or laughing at pretty much every single guess.
  • Nick not even letting Ken finish his reasoning for his guess for the Lambs before getting the crowd to start booing.
  • Jenny crushing Ken's hand during the season's final unmasking.

Season 9

  • Nick introduces the new gimmick of the season in the form of a giant bell, which has been hilariously dubbed the "Ding-Dong Keep It On". Nicole then wastes absolutely no time in slamming Nick.
    Nicole: Someone should have told you that, Nick!
  • While the season continues last season's trend of various celebrities giving out clues, there's one noteworthy exception to this during ABBA Night... a child dressed as Napoléon. Because "Waterloo".
  • Rock Lobster/Howie Mandel is an absolute riot during his time on the show. Highlights include:
    • During his clue package, he calls his past self a neurotic weirdo...and then admits he still is.
    • He completely stumbles his way through "SOS" and, to end the song, tries to walk off stage, only to be stopped by two Men in Black.
    • When the judges are getting ready to guess, he mocks them by saying he's an Excellent Judge of Character and because of that, he knows none of them are getting him right.
      • Which makes it even funnier when Ken gets him right.
    • As he's getting ready to unmask, he quickly takes off the massive claw gloves and still can't get the mask off by himself.
    • Once unmasked, Howie admits that, since Jews aren't supposed to eat lobster because it's not kosher, being in a lobster was even weirder.
    • After being unmasked, Howie learns about the bell and calls the judges out for not saving him.
  • After the California Roll's performance, Nicole begins to lampshade just how bizarre this show can become at times, given that she just witnessed five wads of sushi singing a Broadway rendition of Lady Gaga's "Paparazzi".
  • Ken's guess for the California Roll is the cast of High School Musical, but he can only name three of them.
  • As Nicole performs "Holding Out For A Hero", Ken jumps out on stage and she pushes him away.
  • Ken's reputation for bad guesses has clearly begun to precede him, as the crowd begins booing before he even finishes, even though some of his fellow judges actually admit it's not too bad.
  • Before the Fairy's performance, Ken and Elmo perform "Elmo's Song" together, only for Ken to hijack the performance and declare it "Ken Jeong's Song". Elmo is not amused.
  • During Sesame Street Night, as Ken goes on another wild guess, Oscar the Grouch reassures him that his guesses are his favorite—because the audience boos at them, and there's no better sound to listen to.
  • When Jenny guesses (and correctly identifies) Malin Åkerman as the Squirrel, Ken (her Couples Retreat co-star), realizing he's gonna guess wrong for sure, makes an Oh, Crap! face and hangs his head in shame on the table.
    • Just the fact that Squirrel outright told Ken they worked together and he still got it wrong.
  • For '80s Night, everyone's dressed to the nines for the occasion... with the exception of Robin, who's dressed like a soldier from the Civil War. As for why? His outfit stems from the 1880s rather than the 1980s like everyone else.
  • Ken tries to explain why he thinks the Doll is Donnie Wahlberg, only to be immediately shut down by both Jenny and the audience. And when he tries to defend his guess, Jenny reveals that she knows for a fact that Donnie isn't the Doll, because he's in the audience right now. Cue a very amused Donnie standing up from his seat and a very embarrassed Ken laying his head down on the desk as the panel erupts in laughter.
  • Upon the reveal of the Moose's costume, Robin remarks that his expression looks like "He's been listening to the same story from Ken for two hours."
  • During Movie Night, Ken is dressed as Mr. Chow, his character from the Warner Bros.-distributed film series, The Hangover. During one round of guessing, Robin compares Ken's getup to a '70s mini-van. Such a van is superimposed onto Ken's face afterwards, to drive the point home.
  • Right before Nick announces the first unmasking on Movie Night, we get a cutaway of Robin nervously squirreling on some popcorn.
  • Also during Movie Night, Nicole precedes the Battle Royale with a parody of Nicole Kidman's infamous AMC promo. It takes so long that Ken has to rush Nicole so she could officially start the duel.
  • As Robin decides to ring the Ding Dong Keep It On Bell to save the Mantis, he accidentally goes in the wrong direction before getting back on track.
  • After being the only person to guess Dandelion was Alicia Witt, Ken gets cocky and goes against the majority when it comes time to guess Lamp and not only does he get it wrong, he falls into the pitfall of being unable to identify someone he personally worked with when Lamp turns out to be Melissa Joan Hart.
  • During the Battle of the Saved, Ken starts directly calling out people who are booing him, such as a woman and a little boy who was giving him a thumbs down.
  • For the British Invasion, Nick reveals to everyone that the night's clue-giver is none other than legendary British actor Gerard Butler. Excitement fills the air... which is then followed up by confusion when one of The Men in Black appears instead. Nick then gets a call from backstage—as it turns out, it isn't Gerard Butler giving out the clues, but the aforementioned Man in Black: Gerard the Butler.
    • When Gerard first appears, he's labeled as "Gerard Butler?".
    • For his later appearances, Gerard is summoned with a bell used to regularly summon butlers in other media.

Season 10

  • Nicole has once again developed a crush on a contestant, in this case S'more. The clincher comes when S'more makes his way up to the panel's table towards the end of his performance to hand Nicole a marshmallow bouquet, then tops it off with a kiss on her hand. Needless to say, Nicole is rendered a speechless, blushing mess.
  • Speaking of S'more, when trying to come up with a guess for him, Jenny starts eating the marshmallows he handed out, prompting Robin to comment that he's not sure if they're real or not.
    Robin: I'm not sure those are real, Jenny.
  • Pretty much anything regarding Pickle, from making pickle related puns in his first song to making remarks on the panel and even Nick.
  • As S'more nears the end of his performance of "Hey There, Delilah", he changes the chorus of "Oh, it's what you do me" to "Nicole, it's what you do to me", continuing the Running Gag of Nicole's infatuation with him... and then S'more changes the chorus to have him address Ken instead.
  • When Pickle is outed to be Michael Rapaport, he immediately launches into a rant telling off everyone who failed to guess him correctly —which includes a bunch of Cluster Bleep-Bombs for good measure.
  • Anteater not really showing much distress when he learned he's in the smackdown with Hibiscus, he's just standing in place not showing much worry. Even the panel comments on it.
  • After getting unmasked, Keyshia Cole lampshades how weird the show is by pointing out that she just lost to a singing Donut. Robin admits that scenarios like that happen a lot on this show.

Season 11

  • Fitting for a known prankster like him, Book (aka Kevin Hart) is a riot in his sole episode, from singing a song of the previous season's winner without even bothering to hide his voice or harmonize and treating it more like karaoke than a singing competition, to pulling a Gremlin and unmasking almost immediately after his performance. Nick, despite being happy to see a friend of his, still has to chastise him for his actions and gets mad when the judges and fans chant his name, before Kevin reveals that everything about his performance, from the intentionally off-key singing to his self-unmask were designed to troll Nick, then deciding to calling his jacket stupid.
  • When trying to justify her guess for Afghan Hound, Jenny brings up how a clothesline in the clue could be a reference to a wrestling move...which she mentions wanting to do on Ken.
  • Rita admitting she's getting sick of Ken's "I know exactly who this is" line after only two episodes.
  • When Ken guesses that Clock is Janet Jackson, no one buys it and Rita tries to use the large prop remote to make Ken stop. Ken ends up sticking with the guess purely out of spite.
  • After Starfish is unmasked as Kate Flannery, she actually forgets she has to do her unmasking reprise and starts walking off stage.

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