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Here's a Deep Look at How The Masked Singer Creates Those Coveted Clues

And why they got easier and harder in Season 6

Lauren Piester

While hundreds of people work on each season of The Masked Singer, there are only approximately four people who know who each of the masked singers are. It's a privilege reserved only for the people who absolutely must know out of necessity. That includes a small team of writers, tasked with handing out the clues to the singers' identities and striking that delicate balance between fooling people, but not making them feel totally foolish. The clues shouldn't be impossible to figure out, but they also shouldn't be too easy. Add that conundrum to the pile of NDAs the team has to sign, and you've got yourself a surprisingly stressful gig. 

The show has aired dozens and dozens of clue packages up to this point, but if you noticed something slightly different about the ones shown in Season 6, you're not alone. The clues somehow got both easier and harder at the same time, which supervising producer Brian Strickland – who doesn't even get to be one of those four people – says was very intentional. 

"There are fewer clues, but they're not as obscure," Strickland tells TV Guide. "They're a little bit more grounded, and there's fewer of them in the packages…In the past, it was more of a stretch, like you would need five different links to get to a clue, whereas now, you see a bunny in a house and you know it's House Bunny." 

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That sounds easier to figure out, in theory, but somehow it isn't. And if you need evidence of that, just look at Jenny McCarthy, who spent the first five seasons of the show dominating the guesses. This season, she was as clueless as the rest and made one of the most embarrassing guesses of all time when she tried to kick Caterpillar off the show by claiming he was Jake Gyllenhaal. (It was Queer Eye star Bobby Berk.) 

"No one says that about the clues changing more than Jenny McCarthy," Strickland says. "I don't know if you've noticed this season, but she hasn't done quite as well." 

And McCarthy was not alone, as the whole panel seemed to struggle more than usual. For instance, they easily caught the Disney Concert Hall, Carnegie Hall, and Cooperstown, home of the Baseball Hall of Fame, in Bull's clue packages, but they never considered that maybe they were all pointing towards the word "Hall," for Todrick Hall's last name. 

"I mean, they're right in front of us, but again, they're not such a stretch," Strickland explains. "They're more cleverly constructed, in a way." 

So how are the clues put together, and how do they evolve throughout the season? Strickland walked us through the process. 

Caterpillar, The Masked Singer

Caterpillar, The Masked Singer


The Initial Meetings 

As soon as a singer is booked on the show, they have a phone call or meeting with the team that produces the clue packages, and the writers begin to map out the story they want to tell over the course of the season, because, as Strickland points out, it's not just about giving clues. There's also a narrative for each singer that may change as the season goes on, but almost always starts with an explanation for why a celebrity would want to go on a masked singing show.

Strickland explained that the singers don't actually have all that much impact on the clues. They share some of their history and their reasons for doing the show, but for the most part, they're not a part of the clue-writing process. 

"They don't have much influence on the clue packages themselves," Strickland shares. "A lot of times, they don't even know what the clues mean. Our clue team sort of knows more about the singers than the singers know about themselves." 

Former Cupcake Ruth Pointer, for example, admitted to Strickland on his Masked Singer podcast that she had no idea what half of her clues were about, but a lot of people figured her out pretty quickly anyway. "There is a method behind the madness," Strickland promises. 

The New Clue Method

Again, there are only about four people who know the singers' true identities, and Strickland is not one of them. He works more closely with the panel, but has become a sort of "gauge" for how well the clues work, because of his pop culture knowledge. He'll watch the packages ahead of time and offer his thoughts on who it might be. "In the last couple seasons, we were finding that [the clues] were becoming a little bit too esoteric or obscure," he said. "So I feel like they're much more straightforward this season, and I hope it made the show more enjoyable to watch." 

Part of making the clues more straightforward also meant they became more universal, so while the clues were easier to understand, they also could apply to more people. While Queen of Hearts was obviously Jewel, a lot of people, including Ken Jeong, also thought she was obviously Renee Zellweger or Kristen Chenoweth, due to the Wizard of Oz-related clues. And so many of Bull's clues seemed to point to a cast member from Hamilton, even when Bull revealed he was not associated with Alexander Hamilton, ruining nearly every guess that most of the panel had. "And that's how we ended up with Ken's fallback being Jesse Tyler Ferguson," Strickland recalled, a real low point in the season. 

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The Evolving Clues 

While the team begins working on the clues and packages far in advance of filming, the events of the season can affect what clues are given. The clue team pays attention to the performances and what the singers say, and how the panelists react. When it was revealed that Bull was a fan of Skunk (who was unmasked as Faith Evans) growing up, that was incorporated into one of his clue packages. "It's a learning process for everyone," Strickland says. 

The team watches to see which way the panel is leaning, and then they adjust or add clues to help push them in other directions. With Skunk, the panel couldn't get Jill Scott out of their heads, so the team went ahead and told them outright that Skunk was not Jill Scott. Strickland hints that people should pay particular attention to those clues given while the singer is on stage, because they tend to be more specific, more direct, and "more defining, more in your face." 

"They escalate in stature to eliminate some of the prior guesses, because our panelists, they tend to get stuck on one thing," Strickland explains. "And then it's sort of a bombshell." 

When clues are given on stage, the singers get a chance to respond or explain the clue. Those responses are not scripted, and often the singer doesn't even know what the clue is going to be. 

"So they have to respond off the cuff, and sometimes you get a great little nugget, and sometimes it's like, 'What does that mean?' They are not really prepped so much. There's nothing scripted about it." 

Strickland confirms that yes, that's a totally scary moment for producers, because the singer could easily reveal way too much, but then the clue team is on hand to keep the panel good and confused. 

Queen of Hearts, The Masked Singer

Queen of Hearts, The Masked Singer


The First Impression Guesses

The panelists have only been competing with their first impression guesses for a couple of seasons now, but it definitely added an extra competitive element to the show. The votes that the singers are competing for are almost arbitrary, but Nicole Scherzinger definitely gets to say she was the winning panelist with three correct first impression guesses. The funny thing is that even when the panelists are correct — like three out of four of them were for Katharine McPhee and David Foster — they forget those guesses over the course of the season as the clues send them in other directions. This season was especially all over the place. "It was the worst first impression tally we've had on the show," Strickland says. "But it was fun." 

The thing about the guessing is that it has almost nothing to do with whether the singers stay on the show or not, but that doesn't stop the singers from being terrified that they might be found out anyway. Both Strickland and Hall theorized that Scherzinger kept her guess for the Bull a secret all season long to keep him from worrying, and to make sure he stayed on the show as long as possible. Strickland also thinks Scherzinger knew none of the other panelists would guess correctly. "[Robin Thicke] kept saying, 'This voice is so good, and I've never heard it before,'" Strickland recalls. "I liked [that she kept it a secret]. But I was dying to know, and she wouldn't tell any of us." 

The Celebrity Besties

The panel was also very thrown when Bull got a shoutout from celebrity friend Matthew Morrison, who made Glee references despite Hall not having been on Glee. The videos from celebrity best friends were relatively new additions this season, and some were more successful than others. Morrison was confusing, but other celebrity friends really sealed the deal on some of the guesses, at least for Strickland. "When I saw Courteney Cox [in a video for Pepper], that's when I realized, because I follow her on Instagram and Natasha Bedingfield is all over her Instagram. It's bold to do that, because somebody like Courteney, if you follow her, you've seen it. If any of our panelists follow Courteney Cox, they're going to know immediately." 

Fewer people, Strickland points out, might know that Hilary Swank and Jewel are besties, or Chris Pratt and Willie Robertson. If you follow either Emily Hampshire or Bobby Berk, you might know they're close, but the panel saw Emily Hampshire and immediately started assuming the Caterpillar was Dan Levy. Those cameo videos, which are likely to return, Strickland thinks, can really go either way. 

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The Take It Off Buzzer: A Cautionary Tale 

One of the most hyped elements of Season 6 was the Take It Off Buzzer, a big red button that a panelist could push if they thought they had figured out the identity of one of the singers. It could only be used once for each of the two groups, and if the panelist was right, that singer would immediately be unmasked and sent home. It was a fun idea initially, but the longer the season went on, the more problems it seemed to pose. 

The Masked Singer is not a cutthroat show. Despite its fever dream-like appearances, it's really a heartwarming display of talent and newfound confidence, and just very silly fun. And now, there was this button that could ruin everything for one contestant for no real reason other than the panelists gaining two extra points towards winning the Golden Ear trophy. The singers were terrified of it, as both Jewel and Hall admitted, and the panel clearly didn't want to be mean. It makes sense that it was McCarthy and Jeong —the two non-singers on the panel — who ended up pushing it. Jeong thought Pepper was Sara Bareilles, which was reasonable. And McCarthy somehow thought that Caterpillar was Jake Gyllenhaal, which was maybe the worst guess of the season. 

"It was kind of a last-minute addition," Strickland admits. "And it was very controversial among fans. You don't want to eliminate a great singer. At first, [the panelists] were all like, 'I'm not using it, I'm not using it.' But then when they started to see that their first impression guesses were wrong, and they weren't doing so well, they wanted those two extra points." 

Strickland isn't sure if the buzzer will return, but if you ask me…I'm gonna vote no. However, we are still waiting for Fox to announce The Masked Singer will return at all.