Masked Singer: 10 Funniest Incorrect Guesses

The Masked Singer has consistently tricked viewers since the show came to the United States in 2019. With vague clues and completely concealed singers, fans of the show have found their guesses tend to be wildly incorrect far more often than correct. Luckily for them, though, their guesses are made in the comfort of their own home rather than on national television.

The panel of celebrity guessers does not have that luxury, with their worst misfires being seen by everyone. Some of their guesses have even been quite funny in retrospect, which adds to the intrigue and fun of the whimsical show. While they might not want to relive their biggest misses, fans certainly have fun doing so.

Barack Obama, Season 1

A former president appearing on the show would, without a doubt, be the biggest reveal the show ever had and probably ever would have. The 44th Commander in Chief, Barack Obama, actually was speculated at one point to be Pineapple on the show’s inaugural season.

Jenny mentioned him in passing before Ken jokingly doubled down on the guess being Obama because one clue insinuated they were from Hawaii. Obama performing with his Secret Service as backup dancers would be breathtaking, but the real celebrity ended up being quite different from the former POTUS, instead being Tommy Chong, half of one of the most iconic stoner duos in film history.

Donnie Wahlberg, Season 1

Jenny was never absolutely certain, but she repeatedly speculated that the voice of Rabbit was her husband, Donnie Wahlberg. Despite presumably hearing his voice nearly every day, she still was mistaken, as Joey Fatone was instead the actual mystery celeb. He was revealed in what many consider to be one of the most unfair eliminations in The Masked Singer history.

Donnie reasonably could have appeared on the show and actually would later on, and if any of the other three panelists guessed him for Rabbit, it would not have been as funny. When a panelist incorrectly guesses her spouse, though, it certainly is going to cause some laughs.

Meghan Markle, Season 1

British royalty probably has more pressing matters to attend to, but this did not stop Nicole from theorizing that the Duchess of Sussex, Meghan Markle, was on the show.

She was guessed due to one of the clues referencing the celebrity having a seemingly glamorous childhood but having struggles under the surface. Markle was a well-known actor who appeared in many movies and TV shows before her marriage to Prince Harry, so it certainly may have fit her, but having someone as high profile as her appearing on The Masked Singer is highly unlikely and an amusing guess.

Ruth Bader Ginsburg, Season 1

Many will give Ken a pass on this one as it was pretty clearly a running joke he started, but it was still quite humorous nonetheless. Ken has been clear that the now late Supreme Court Justice Ruth Bader Ginsburg would have been his dream unmasking, and he tried to speak it into existence throughout season 1.

Ken threw out her name in jest whenever he was unsure of a reasonable guess, with the Unicorn being an example of one contestant he mentioned RBG for. She was given the nickname the Notorious R.B.G, so maybe she did have a secret rapping talent like B.I.G.

Mariah Carey, Season 4

Ken is known for giving off the wall guesses, but this one was downright hysterical. Lips ended up being voted off of the show after just one performance, being unmasked to reveal talk show host Wendy Williams. Ken’s first impression guess was not particularly close, as he landed on superstar pop icon Mariah Carey.

Not only is it a bit insulting to Mariah that he thought she would sing similarly to how amateur singer Wendy Williams would, but it was even funnier considering who the show’s host is. Nick Cannon is the voice of The Masked Singer, as well as Mariah’s ex-husband. It could have been slightly awkward if it was indeed Mariah.

Akon, Season 5

Guessing Akon is not exactly comedic, as he realistically could appear on the show and has a great singing voice. Jenny McCarthy finalized him as her guess for one-time performer Cluedle-Doo. She probably should have known better, though.

Turns out, it was Jenny’s husband, Donnie Wahlberg, behind the mask. One would assume she would have known this, especially since Donnie used to sing professionally as a member of the boyband New Kids On The Block. She was visibly shocked, as is to be expected for not recognizing the voice of someone she lives with. At least she did not give the way-too-common guess of Jamie Foxx like some of her fellow panelists did for Cluedle.

Morgan Freeman, Season 5

Having one of the most iconic voices in Hollywood history, if Morgan Freeman ever appeared on the show, it would probably be fairly obvious to tell it is him. Jenny ended up having him as one of her various guesses for the Grandpa Monster, who ended up actually being social media star Logan Paul.

Logan Paul and Morgan Freeman being mixed up for one another is something nobody would ever anticipate happening, making this so funny. Paul also showed off his dancing skills while performing, moving in a way that an 84-year-old Freeman might find difficult.

Danny DeVito, Season 5

One of the stars of the always funny sitcom It’s Always Sunny In Philadelphia, Danny DeVito is known as being one of the funniest actors right now. Despite his comedic prowess, he also is always associated with his stature, being slightly over 5 feet tall. This did not stop Ken from guessing him for a costume that was most definitely not built for someone who was that height.

Ken guessed the wrong Danny, as iconic zombie movie star Danny Trejo was the man behind the Racoon costume. Trejo is half a foot taller than DeVito, so it is practically impossible that DeVito could have performed in that costume.

Chuck Norris, Season 6

There was a time in the early age of internet memes that Chuck Norris was considered royalty. He was constantly the subject of widely shared jokes, with the punchline always revolving around Chuck Norris being incredibly tough or even invincible. Hearing his name pop back up in 2021 was a fun moment for anyone who experienced those days.

Robin guessed him as possibly being Baby, but it instead turned out to be Larry the Cable Guy. It was a nice reminder of Norris being such a funny and iconic name a decade prior for reasons completely unrelated to his extensive acting career.

Bill Clinton, Season 6

While this one, unfortunately, did not air on the official broadcast of the show, Ken disclosed his slightly silly guess on the official The Masked Singer podcast. He took a break from guessing former U.S. presidents and justices, but he came back by guessing Bill Clinton as the Mallard.

He hypothesized this due to clues involving the South, where Clinton was born, and saxophones, which Clinton is famous for playing. It instead turned out to be Willie Robertson, former star of Duck Dynasty. Clinton certainly would be an interesting guess to have, but he really does not have much to gain or prove at this point.

About The Author