Top 20 Most Shocking Reveals on The Masked Singer

The fifth season of “The Masked Singer” spiced things up and introduced Cluedle-Doo. A combination of a rooster and a court jester, Cluedle-Doo would appear and provide viewers extra clues about the contestants. He eventually took the stage himself, singing “Return Of The Mack” by Mark Morrison. Guesses ranged from Kevin James to Jamie Foxx to Akon. But the truth ended up being far more surprising. It was actually Donnie Wahlberg, who also happens to be panelist Jenny McCarthy’s husband! The fact that she didn’t manage to guess her own partner is just hilarious, and yes, she was embarrassed about it.

This performer didn’t last long, but he sure left an impression. Jack in the Box sang just one song - George Thorogood and the Destroyers’ “Bad to the Bone.” Unfortunately, the celebrity drummed up quite a bit of controversy, and his reveal was leaked before the episode had a chance to air. It was President Donald Trump’s personal attorney and ex-New York Mayor, Rudy Giuliani. Giuliani is quite a contentious figure owing to his involvement in the Trump administration. The reveal caused an upset Ken Jeong to leave the set, with Robin Thicke following him. Even though it was spoiled beforehand, the unmasking of Rudy Giuliani was quite a shock to the system.

Known for her singing, fashion, and talk show appearances - not to mention her famous parents - Kelly Osbourne is a household name. That’s why it’s so wild that the panel didn’t realize she was Ladybug! The bright red insect appeared in the second season, performing four songs in total (smackdown included), before getting eliminated in week six. For their final guesses, Robin, guest panelist Triumph, and Ken all guessed Lindsay Lohan. Jenny, for her part, went with Paris Jackson, while Nicole guessed Jamie Lynn Spears. Imagine their surprise when the truth was revealed. Osbourne’s fake Southern accent certainly helped throw them – and lots of folks watching – off the scent. Hey, no one said fake voices were against the rules!

It’s always a nice surprise when non-singers go far. Jellyfish stunned everyone in season four. She made it all the way to the penultimate episode and even won week nine with a stunning rendition of Dua Lipa’s “Don't Start Now.” There were even a few good clues, like the four x’s on the tic tac toe board representing X Games gold medals. Well, she can add “The Masked Singer” to her long list of accomplishments, as this was Olympic gold medalist, snowboarder Chloe Kim. The nods towards Jellyfish’s athleticism clued in Ken Jeong and guest panelist Craig Robinson, both of whom made correct guesses in the end.

Like Chloe Kim, the reveal of Larry the Cable Guy was unexpected owing to his surprising talent as a singer. As Baby, he notably performed a decent rendition of Barry White’s “You're the First, the Last, My Everything,” which likely threw the panel off for good. In fact, Ken Jeong once falsely identified Larry the Cable Guy as Banana back in season three. Even funnier, Robin Thicke initially thought that he was another contestant on Baby’s season, Mallard. Poor guys were so close yet so far. For Baby, Jeong ultimately went with Gordon Ramsay and Thicke with Chuck Norris. Larry the Cable Guy was clearly on their minds, but they just couldn’t figure him out as the giant Baby.

Tom Bergeron is an iconic television host, and millions of people have been hearing his voice for years. It’s so recognizable that we should have pegged it instantly. There were even a few obvious clues, like the VHS tapes representing “America’s Funniest Home Videos.” Instead, Taco’s identity came as quite a surprise. Both Robin and Ken ultimately guessed Martin Short, prompting the latter to put his hands on his head upon the reveal. Even Bergeron seemed flabbergasted that no one correctly figured him out, as nearly all the panelists were friends or associates. Put simply, the reveal of Tom Bergeron was just a whirlwind of confusion.

Clearly athletes also make for pretty darned good singers. Thingamajig went far in season two, blowing us away with his performances and eventually placing in fifth. He even tackled a few singers whose tracks are not easy to nail, including Michael Bublé, John Legend, and Bing Crosby. And yes, he more than held his own throughout the competition. It all contributed to making the eventual unmasking extra jaw-dropping. Thingamajig wasn’t mainly a professional singer, as some viewers had maybe assumed, but basketball player Victor Oladipo. Ken Jeong was talented enough to get it right, but pretty much everyone else was totally surprised, and for very good reason. Those who want to hear more of Oladipo’s stellar voice should check out his albums, though!

Jackie Evancho became a household name when she competed on the fifth season of “America’s Got Talent” at just ten years old. This in turn helped launch her successful music career, which includes the platinum-selling EP “O Holy Night” and several successful albums. She did well as Kitty on “The Masked Singer”, slaying songs like "It's All Coming Back to Me Now" and finishing in fifth place. And she stumped everybody. No one had her identity figured out in the end. Even Nick Cannon – who got to know her when he was hosting “America’s Got Talent” – seemed genuinely taken aback. If not even he could predict the celebrity under the mask, viewers at home had absolutely no chance!

We mentioned Banana before, as Ken Jeong thought that he was Larry the Cable Guy. Well, as you know, he was way off. Banana was not a comedian, but professional singer Bret Michaels, who’s primarily known as the frontman of Poison. But what’s surprising about this reveal is arguably how unsurprising it was. Everyone but Ken Jeong correctly guessed Bret Michaels, with guest panelist Sharon Osbourne fully convinced it was him under the mask. Maybe the clues were too obvious, or maybe his voice is simply too recognizable. It almost made it hard to believe it was actually him, considering “The Masked Singer” is usually better at concealing singers’ identities.

Like Bret Michaels, Gladys Knight was pegged by pretty much everyone. Once again, Ken Jeong was the only panelist to make an incorrect final guess, as he went with Anita Baker. So sure, maybe the reveal itself wasn’t all that surprising. But if you ask us, the sheer mythical quality of Gladys Knight herself made it an unmasking for the books. Indeed, “The Masked Singer” got themselves a real legend. The Rock and Roll Hall of Fame inductee has too many amazing accomplishments to even list, including multiple Grammys and number one singles. It was a huge boon to the show’s popularity and credibility, proving that the producers could get the big names.

“The Masked Singer” needed a hip hop star, and the Chameleon was its answer. Placing in third, the Chameleon wowed both the audience and the judges with strong performances of various hip hop classics, including “Drop It Like It’s Hot” and “Gangsta’s Paradise.” The final guesses ranged between Gucci Mane, 2 Chainz, and Wiz Khalifa, and the latter was correctly guessed by Robin Thicke and Nicole Scherzinger. Perhaps it didn’t come as a huge shock given the correct guesses, but Wiz remains one of the biggest names that the show has ever revealed. The recipient of three platinum-selling albums and four top ten singles, Wiz is a bonafide rap superstar.

Despite being a prominent R&B artist, T-Pain surprised everyone with a number of popular rock and pop songs. These included Queen’s “Don’t Stop Me Now,” Lenny Kravitz’s “American Woman,” and Sam Smith’s “Stay with Me.” Perhaps this, combined with the lack of his signature autotune, is what made the eventual T-Pain reveal so unpredictable. In fact, none of the judges correctly assumed T-Pain’s identity, with all five guessing someone different (including Jamie Foxx and Michael Vick). T-Pain ended up winning as The Monster, and it concluded the show’s first season on an excellent note. With it, “The Masked Singer” proved that it had the capabilities to shock and surprise millions.

Video game streamer Ninja appeared in one episode of the second season as Ice Cream. He performed Lil Nas X and Billy Ray Cyrus’s “Old Town Road” and pulled out Devo’s “Whip It” during the smackdown with Ladybug. Unfortunately, both of his performances proved lackluster, and he was the first person of the group sent home. His clue package had various references to gaming, leading Ken Jeong to guess PewDiePie. It was the closest anyone would get, as no one was expecting megastar Twitch streamer Ninja. We’re sure some of the younger viewers were able to identify him, especially with the helpful karate chop clue. But the rest of us were as flabbergasted as the judges.

Despite being the Grandpa Monster, it was very obvious that someone young was underneath the costume owing to their wild energy. In fact, Logan Paul is the second youngest male contestant in the show’s history, being just 25 at the time of his unmasking. Grandpa Monster lasted two weeks, remaining safe with his performance of “Mambo No. 5” but losing with Joan Jett’s “Bad Reputation.” Various clues led to Nicole guessing Jake Paul, Logan’s younger brother. Maybe it wasn’t a big shock for her, but the reveal proved hugely surprising to the rest of us. Turns out, Logan Paul really knows how to put on a good show!

Mickey Rourke was the last celebrity we expected to see on “The Masked Singer.” Rourke often plays tough guys on screen and is a bit of a tough guy himself, even going undefeated during his professional boxing career. Rourke appeared as the Gremlin in the show’s fourth season and performed Ben E. King’s “Stand by Me.” However, Rourke began to feel hot inside the costume and unmasked himself in a moment of shocking unpredictability. We don’t know how much of that was pre-planned, but both the premature exit and the reveal of Rourke made for one of the most memorable moments in “Masked Singer” history.

If nothing else, Busta Rhymes’s Dragon costume was amazing. It’s just a shame we didn’t get to see much of it. Rhymes appeared in just one episode of the show’s fourth season, performing LL Cool J’s “Mama Said Knock You Out.” Both Robin and Nicole were on him from the very beginning, and both made Busta Rhymes their first impression guesses. And then there’s Ken guessing Michael Phelps. Not sure what happened there. While the reveal wasn’t too surprising owing to the confidence of Robin and Nicole, it was still quite a shock seeing Busta Rhymes go home so early. You’d think a 12-time Grammy-nominated artist would have stuck around a little longer. Maybe his voice was just too recognizable...

This is another case of a kickass costume gone way too soon. Appearing in just one episode of the third season, the Elephant performed The Cure’s “Friday I’m in Love.” Unfortunately, the performance was deemed lackluster and poor Elephant received the boot. When it comes to “The Masked Singer,” fans are typically guessing the likes of musicians, actors, and internet or talk show personalities - not professional skateboarders. Perhaps this is why none of the judges guessed Tony Hawk. In fact, no one was even close. Despite being a household name, absolutely no one was expecting to see the skateboarding legend behind the mask. Still, it was a welcome surprise.

Tell us you expected Sarah Palin to be on “The Masked Singer” and we’ll call you a liar. This is undoubtedly one of the show’s most unexpected reveals - not only owing to the mere presence of Palin, but because she performed - of all songs - Sir Mix-a-Lot’s “Baby Got Back.” It’s an unexpected song from an unexpected guest, and that’s what “The Masked Singer” is all about. Palin also made history from her tenure, including being the first female to rap and the first political figure to appear on the show. It was great seeing her let loose and have some fun, and the audience had a ton of fun alongside her.

“The Masked Singer” has scored some big names, but few as big as Lil Wayne. This rapper has released nine platinum albums and 26 platinum-selling singles. In fact, he is one of the highest-selling musical artists in history, having pushed over 120 million records throughout his career. Getting a legend like this on a singing competition is a very rare occurrence, and it made Lil Wayne’s reveal an unforgettable moment in “Masked Singer” history. He appeared in the third season as Robot, but unfortunately didn’t last very long. He finished in last place, having received a poor reception for his rendition of “Are You Gonna Go My Way.”

Is having Kermit the Frog on “The Masked Singer” sort of cheating? Maybe. But it was still a ton of fun. Kermit appeared in the fifth season as The Snail. It was a brilliant bit of costume design, allowing puppeteer Matt Vogel to remain out of view because he stayed inside the shell, in which a motorized wheelchair was reportedly installed. Kermit performed Hall & Oates’s “You Make My Dreams (Come True),” and hearing it now, the singer’s identity couldn’t have been more obvious. But no one had any idea it was him, with guesses ranging from comedians like Seth MacFarlane and Billy Crystal to Ted Cruz. This was one of the most memorable reveals from the show, but guessing a fictional character would have been near impossible.