Craziest Moments On The Masked Singer

Hello everyone!

As we are still in the midst of a new season of The Masked Singer being taped, as well as a trailer for that same season being released over the weekend, I feel it only makes sense that I do another blog post about the show!

As I’m sure you’re all aware, the show is a strange show, but sometimes it has some REALLY crazy moments. Moments that make you wonder “What even is going on?” In today’s blog post, I will be discussing what I feel are the craziest moments of the whole series. I will be starting with a fairly calm example, and then working my way up to the craziest moment of the whole series.

The first moment comes from Season 5, and it is brought to us from the contestant Robopine, who was revealed to be R&B singer and actor Tyrese Gibson. The show has Clue Packages that serve as hints to who is underneath the mask, and they also tell us stories about each contestant. Tyrese chose not to do that, instead giving clues such as how he was a 60 year old grandfather from Costa Rica, none of which are true, and he also said these things more than once as clues. He described this as him getting into character, and said that his reason for lying in his Clue Package was because of how well all the panelists knew him. This makes Tyrese Gibson the first and so far only contestant to lie in his Clue Package.

The next moment comes from Season 9 from the contestant The Wolf. Typically the way we are introduced to contestants for the first time is when they first walk onto the stage. The Wolf did not do that. Instead, a flash of lightning appeared, and then The Wolf just suddenly appeared on the stage. I don’t know whose idea it was to do that, but I am glad that they did it because it was funny and perfect for him.

The next moments happened in both Season 6 and Season 9. As I’m sure you can probably guess, there is a lot of planning that goes into making a season of The Masked Singer, including a number of rehearsals. In these two seasons, something happened that resulted in contestants having to literally make last minute changes. In Season 6, Natasha Bedingfield was cast with 24 hours notice, and in Season 9, Sara Evans had to make her debut an episode early and perform a completely different song from the one she had been practicing with 24 hours notice, and Debbie Gibson was cast with 24 hours notice as well. So these are three contestants who had very little time to learn songs, and two celebrities who also had essentially no time to get accustomed to their costumes… and they were amazing on the show. In fact, I would even go so far as to say that they are among some of the best contestants the show has ever had. It really serves as a testament to their singing abilities, that they were able to give such amazing performances with essentially no practice at all.

The next moment happened in Season 12, which started off in the weirdest way imaginable, which is saying a lot. It started off for some reason with an introduction by William Shatner of all people, where he was explaining the show. I know that he was a contestant on Season 8, but what was he even doing there? He didn’t appear again throughout the entire episode, and he didn’t appear again during the season, and he was not a Masked Ambassador for any of the contestants. So, why was he even there introducing the show?

The next two moments happened in Season 8. In this season, there were many celebrity guests that served as guest clue givers, but there were two celebrity guest appearances that were just bizarre. The first one came in the first episode, when Will Arnett made a completely random appearance out of nowhere, and left as soon as he arrived. I literally have no idea why he was there other than because Lego Masters. The other bizarre guest appearance was Drew Carey on Comedy Roast Night, as he was only there to introduce the Battle Royale. I have no idea why they did this, as they literally could have just had Nick do it, or they could have had guest clue giver for the episode Jon Lovitz introduce it. I have no idea why they brought Drew Carey on to do absolutely nothing.

The next moment happened in Season 11. In the Premiere, the last contestant was The Book, and from there, everything went off the rails. He gave a truly terrible performance of So Sick by Ne-Yo, during which he didn’t even try to disguise his voice, and after he was done, he unmasked himself and revealed that he was Kevin Hart. While this was already bizarre enough, things got even stranger, as Kevin Hart kept insisting that he had pranked Nick Cannon, at which point I find myself channeling my best Tim Robinson and asking “What’s the joke exactly?” I have no idea what it could have been. Was it that he gave a bad performance? If so, he wasn’t the worst singer the show has ever had. And if the prank was that he unmasked himself, another contestant had already done the same thing several seasons before, which I will get to later. So, even though it was funny, I have no idea what the prank was supposed to be.

The next moment happened in Season 6. Whenever we meet a contestant for the first time, they enter from either side of the stage. The Jester chose not to do this, instead entering through a door in the audience, and then walking through the audience on his way to the stage, all while the song We No Speak Americano was playing. Things would only get much crazier during his second performance, where he chose to perform I Am A Man Of Constant Sorrow by Soggy Bottom Boys of all songs. For those of you who don’t know what that song is or what that band is, which I imagine is every one of you, it is a bluegrass song performed by a fictional band. Yes, you read that correctly, and while the song is actually from 1913, this version is technically by a fictional band from a movie. Not only that, but The Jester also performed it in the weirdest country accent I have ever heard in my entire life. And to make things even weirder, he was then unmasked to be Johnny Rotten from The Sex Pistols. Yes, everything I was just talking about with The Jester, was really about Johnny Rotten. Go ahead, try not to picture this.

The next moment happened in Season 5, with one of the most bizarre unmaskings to date. At this point in the show, all the unmaskings had been real people, and ever since this moment, that has continued to be the case. However, in the Season 5 Premiere, something very surprising happened. The first contestant who was unmasked was The Snail, which was surprising, because he was far from the worst contestant that night, despite the fact that at the time, I felt he had a weird sounding voice. As soon as they unmasked The Snail costume, by removing the hat from its shell, things got weird, as nobody was there. A few seconds later, two familiar looking small green arms popped out the shell, and then out popped none other than Kermit The Frog. When I first saw this, I couldn’t believe that they had a fictional puppet character as a contestant, and I still can’t.

The next moment comes to us in Season 10. Typically, contestants talk about how much fun they had after they get unmasked, even celebrities who are vocally bitter after the fact about their unmasking. However, there was one contestant who didn’t even hide his anger at being unmasked, and resulted in an unmasking that quickly went off the rails. In 2000s Night, the contestant unmasked was The Pickle, who was revealed to be actor, comedian, and podcast host Michael Rapaport. As soon as he was unmasked, he WENT OFF on all the panelists, one by one, ranting about how he was amazing, ranting to the audience and the panelists again for sucking up to him after he got unmasked, and this all resulted in the show being censored more than it has ever been before or since. Normally I feel that I can tell if a celebrity is pretending to be upset about something like getting unmasked, but in this case, I literally can’t tell at all because how he acted when he got unmasked is no different from how he is in real life. I’m genuinely surprised by how much of this moment they kept in, as the show is rated TV-PG, and they had to censor a lot of what he said, and his rant definitely clashes with the wholesome tone of the show, but they left it in because they thought it was funny, and I am so glad they did because it might actually be the funniest moment of the entire series.

The next moment happened in Season 6, and it’s all at the hands of one contestant, The Baby, AKA, Larry The Cable Guy. First of all, the costume itself was very bizarre, as it was a giant realistic looking baby, and things only proceeded to get weirder. In his Clue Package, he spoke with a weird fake Cockney accent for some reason, and also described himself as being part of a Baby Rat Pack, having blockbuster hits, award winning albums, radio play, and having replaced Schwarzenegger in a film. It then got even weirder during his first performance of You’re The First, The Last, My Everything by Barry White, where he sang the first part in a weird nasally sounding voice, before abruptly, and I mean abruptly, switching over to an operatic tone. And believe it or not, things get even weirder, as for his second performance, he performed the theme song to The Flintstones. Yes, you read that correctly. And you are not going to believe this, but it gets weirder, as he sang the first verse in the weirdest operatic tone I have ever heard. 

And here’s the craziest part. With everything that I just said about Baby, you might think that nothing on the show could be crazier. And to that I say, you are very wrong.

The last moment comes from Season 4, and it has got to be the craziest moment of the entire show, because it goes off the rails so fast and leaves you with a million questions. 

It’s time to talk about The Gremlin. 

In Episode 2 of Season 4, the final performer was The Gremlin. Things started off normal with his Clue Package, but from there, things took a turn.

He then went on to give a very bizarre performance of Stand By Me, where there were two instances where he turned two one syllable words into a single one syllable word. What I mean by this is that there was no pause between the two words, making it sound like a single word. When it comes to his voice, I’m going to defer to what Jenny said after his performance, when she asked “Is he 100 years old?” I would also like to add that the celebrity was 67 at the time.

Things only got much stranger after that, as he said that he performed the song as a tribute to his friend Willy DeVille. I find this very bizarre because the song is originally by Ben E King, while Willy DeVille only covered it for one of his live albums. My point is that if he wanted to pay tribute to Willy DeVille, why didn’t he just sing one of his own songs? Or did he try to get permission to do so, and ended up having to settle on a song that he covered on one of his live albums?

Then, in a truly outrageous moment, when the panelists were making their guesses, Jenny managed to guess correctly, which my dad found very surprising, which I feel was because there was very little in the clue package to immediately point out that it was this person.

From there, things got even more outrageous, as Gremlin then said that it was too hot in the costume, and began to try removing the mask, and despite some protests from Nick and the panelists not to, they were unsuccessful.

There is a reason why I haven’t said who was underneath the Gremlin mask yet. It’s because I know that none of you reading would ever guess in a million years who it was correctly, and you also won’t believe it as you are reading it. 

Gremlin then removed his mask himself, and the celebrity inside was revealed to be none other than…

Mickey Rourke.

Yes. You read that correctly. The actor and the former boxer, that Mickey Rourke. The star of movies like The Wrestler and Iron Man 2, that Mickey Rourke.

I have so many questions now because of this one unmasking, that I need to share them all.

Why did the producers even think of casting Mickey Rourke in the first place?

How many other celebrities turned them down before they asked Mickey Rourke?

Why did Mickey Rourke even agree to do the show?

Did anybody working on the show know he was going to unmask himself?

Things got even crazier, as after he removed his own mask, he literally threw it into the audience, to which I have two questions, which are did he break the mask? And did he get in trouble for throwing it?

And perhaps most bizarre of all, there was a visible pink kiss mark on his cheek. I don’t know why it was there, I couldn’t explain why if I wanted to, and I feel like I should be worried to find out.

Things only continued to get crazier, as when Nick asked him why he did the show, his response was that he was in the neighborhood. I am not making this up, that is actually what he said. 

Things then got weirder, as he then said that he liked the show, and that he watched it from the beginning after he was asked to be on it, and that he had watched four episodes. I would like to remind you all that he was a contestant on Season 4. 

Things only continued to make less sense, as Robin then said that he and Mickey Rourke hung out a few times together down in Miami, to which Mickey responded by shushing him. I don’t know what this means, and I don’t want to know what it means, because it’s definitely something horrifying.

Then we got the most bizarre unmasked performance yet, as Nick joined him for an encore of Stand By Me, which seemed like he was trying to help Mickey get through it, and they cut the performance off before they even got to the chorus, at which point Mickey Rourke began to walk backstage.

Nick Cannon then said one of the funniest things he has ever said, as he said that we had been watching “Mickey Rourke Presents The Masked Singer.” 

To sum up everything that I just wrote, I am instead going to share with you all what Nick said right after everything went down, which sums it up better than I ever could, “I don’t know what just happened.” 

Five years later, and I still don’t understand what happened in this moment.

I hope you all enjoyed reading this blog post, and I’ll see you all soon with another one!