Masked Singer’s Serpent Is Probably A Hamilton Alum — Just Not The One You Think

Photo: Courtesy of Fox.
While the Masked Singer's group-per-week format is no longer new, the series is finding plenty of ground to break in season 4. First, The Masked Singer introduced its dystopian faux-audience trick, and now it's giving us The Serpent: a ridiculously talented singer whose tentacles literally move on their own. Disney's Imagineers are shaking. Who could merit such red carpet treatment?
Well, first let's consider the caliber of Group B. I am not being dramatic when I say they blow Group A out of the water. This group is packed with some frontrunners and one of the most talented singers is the Serpent. Between his animatronic arms and the intimidating snakeskin costume, the Serpent’s powerful presence on stage is amplified when he starts singing. Similar to the Leopard in season 2, the Serpent stays in character when talking to the panel which makes guessing his identity infinitely more difficult — and a lot more fun. He is definitely going to be around for a long time with that silky smooth voice, but there's no time like the present: let’s get a jump start on figuring out who's behind the mask.
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Leslie Odom Jr.

The panel, specifically Ken Jeong and Nicole Scherzinger, were picking up on multiple Hamilton connections in the clue package. Scherzinger suggested Leslie Odom Jr., who won a Tony Award for playing Aaron Burr in Hamilton. There was a map of the Caribbean shown in the package and the Serpent was sitting in a library with a stack of books next to him. In Hamilton, the characters, including Burr, mention multiple times that the titular character is an immigrant from the Caribbean. Also, the musical is based on American history and the life of Alexander Hamilton, which could explain the books.
Two signs are shown in the package — one says “medicine” and the other “musicology.” The musicology sign has a clear connection to Odom since he is a remarkable singer. The medicine clue is less obvious but it could be a reference to Odom’s acting career. He played a doctor in the star-studded 2017 movie Murder on the Orient ExpressHe's also got plenty of his own music to promote:
The final clue is the one that directly points to Odom which, as a Masked Singer aficionado, makes me think there's no way Odom is behind the mask. In the first ever Serpent clue package, an animated Serpent speaks to Serpent, Sr, implying the masked musician is referred to as a junior. That would give Odom’s identity away in an instant. And there's just no way this show would make his first clue package that easy to decipher. It's also very possible the show is trolling fans who thought they figured out Odom's identity before the Serpent episode even aired.
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Scherzinger was committed to her Odom guess so it was surprising to see that none of the judges mentioned him after the Serpent performed his second song, “The Bones” by Maren Morris. While the panel might have abandoned this hunch, there were a few moments in the clue package that make Odom’s appearance on the show still plausible. 
The new set of clues focused on Serpent’s past. He said singing as the reptile “has been a childhood dream come true.” This could mean Serpent is someone who started performing young. Odom attended the Philadelphia High School for Creative and Performing Arts and he also studied musical theater in college
Serpent admitted that he could barely pay rent at the start of his career. Odom is known for Hamilton, but his Broadway debut was in Rent. The clue could have been dropped in the package to throw the panel off and make them consider Broadway stars whose names are more synonymous with popular musicals.
The panel pointed out that Serpent was holding a trophy throughout the package. Odom won a Tony Award for Best Actor in 2016 for his role as Aaron Burr and he was also awarded a Grammy for Best Musical Theater Album. These few clues are enough to keep Odom as a viable option to be behind the sleek figure. 

Taye Diggs

Jeong was on the Hamilton train too, but he theorized that Daveed Diggs was wearing the mask based on the book with the title “How To Dig Yourself Out of Debt.” This clue is significant but I think it is pointing to another notable Diggs with a theater background: Taye Diggs. He's known for roles in Broadway musicals Rent and Hedwig and the Angry Inch, so he can definitely sing. 
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If Diggs is inside the costume, the clue package focused more on his acting career to throw the panel and the audience for a loop. He became a household name when he starred in his debut film How Stella Got Her Groove Back. In the movie, Stella (Angela Bassett) meets Taye’s character, Winston, during her Caribbean vacation which explains the map in the clue package. The “medicine” sign also points to this movie because Winston wants to become a doctor. 
The Serpent’s demeanor after his first performance of a slowed-down rendition of The Proclaimers' hit “I’m Gonna Be (500 Miles)” was the most convincing evidence that Diggs is masquerading as a giant snake. Since Diggs’s television show All American has had its production delayed due to the COVID-19 pandemic, he has kept himself busy posting hilarious videos on his Instagram in character as a fitness instructor. Diggs is a funny actor who fully gets into character and the Serpent could just be his latest role. 
Only a couple clues in the second package pointed to Diggs being Serpent’s true identity but they were significant enough that panelist Jenny McCarthy noticed them. She suggested Diggs and her reasoning was solid.
The “barely make rent” clue obviously connects to Diggs. He originated the role of Benny in Rent on Broadway. He reprised his part for the 2005 film version of the musical and he also appeared on stage during Rent Live! last year on television. 
When Serpent spoke about his early struggles, a pair of scrubs was highlighted in the back of the scene.  Diggs played Dr. Sam Bennett on the medical drama Private Practice for six seasons. The scrubs also link to the medicine-related clues in the previous clue package. 
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Serpent’s childhood clue was a baby bottle filled with milk on wheels. Diggs and his son posed together for a Got Milk campaign in 2013. He is the only prediction who connects in some way to milk. 

Brandon Victor Dixon

The panel thought that the Rent clues connected to someone who was known to star in the Broadway production of the musical. But, they are forgetting about the recent live musical trend that television networks have been following. It is possible that Fox’s Rent: Live star Brandon Victor Dixon is Serpent.
Although this is a new guess, a few of the clues from Serpent’s first episode connect to Dixon. The first packaged was stuffed with hints suggesting someone from Hamilton is inside the costume. Dixon starred as Aaron Burr in the musical after Odom departed the role in 2016 and he played the lead character for about a year. 
Another television musical that Dixon starred in was Jesus Christ Superstar. He played Judas Iscariot, Jesus’s adversary. In the second clue package, Serpent says that he “heard no from the gatekeepers.” Jesus Christ is sometimes referred to as a gatekeeper and the musical centers on disagreements between Judas and Jesus. 
The award in the clue package could represent Dixon’s Tony Award which he won in 2014 for his work as a producer of the Hedwig and the Angry Inch revival. Plus, like all the other men on this list, he has a range similar to Serpent and is more than capable of hitting high notes. 
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Christopher Jackson

My final theory is the strongest, if I do say so myself. The panel guessed multiple Hamilton cast members but they didn’t suggest the person who has the range and tone most similar to the Serpent: Christopher Jackson, who played George Washington.
Washington was one of Jackson’s biggest roles but he also originated the part of Benny in Miranda’s other musical In the Heights. During the clue package, the Serpent said he had the “fire to aspire to new heights,” possibly a nod to the play's title. He also said it took “a string of miraculous events to get here.” The strings could refer to an orchestra. Jackson is also a composer and has been nominated for multiple Emmy Awards for his music. 
Before the premiere, The Masked Singer aired a preview episode that introduced all the season 4 contestants. The Serpent’s teaser clue was a prescription bottle. Jackson currently stars on the show Bull, about a psychologist. He also appeared on Fringe as an EMT and on another medical drama Nurse Jackie
During his performance, the Serpent hit multiple notes that were similar to the way Jackson sings the song “One Last Time” (above) in Hamilton. Also, compared to Odom and Diggs, Jackson’s build and height matches the Serpent a bit better.
Some new clues built upon the hints in Serpent’s first package that support this Jackson theory. Serpent is holding a trophy in his clue package and Scherzinger noted that it could represent someone who has been nominated for an award but never won. In addition to his Emmy nominations, Jackson was recognized for his role in Hamilton in the Best Featured actor category, but he did not win. 
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The scrubs that were shown are another link to the medical dramas Jackson has appeared in like Nurse Jackie and his current role on Bull. The scrubs were on a mannequin in a clothing store. Serpent also spoke about clothes in the clue package.  Jackson’s character on Bull is a fashion stylist. 
In one scene, Serpent is electrocuted and there is a sign that says “Danger Electrical Transformation.” In 2009, Jackson wrote music for a children’s show called The Electric Company. It was much more difficult to connect Serpent’s second set of clues to Jackson, but there is still enough here to keep him as my top contender. 
This post has been updated. It was originally published on Sept. 30, 2020.

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