The Masked Singer: 10 Most Shocking Season 2 Reveals, Ranked

Ever since The Masked Singer began airing on FOX in January 2019, a vast selection of celebrities have been unveiled in elaborate costumes in the three seasons to date. Season two aired from September to December 2019. While the first season featured names such as Gladys Knight, Donny Osmond, Joey Fatone, and Rumer Willis, there were even bigger surprises being unmasked.

Read on for the ten biggest shocks that occurred throughout The Masked Singer’s second season. From singers, actors, comedians and many more, there was someone for everyone to enjoy.

10 Ice Cream: Tyler “Ninja” Blevins

Gamer and YouTube celebrity Tyler “Ninja” Blevins was one of two celebrities revealed in the season two premiere. Disguised as the Ice Cream, he sang “Old Town Road” by Lil Nas X and Billy Ray Cyrus in his main performance as well as “Whip It” by Devo in an unsuccessful attempt to avoid elimination. Unlike many of season one’s contestants, Ninja specifically catered to a younger demographic who would be excited to see him on this show, regardless of the short stint.

At the time that his reveal was filmed, Ninja was streaming on Twitch and later moved to Mixer.  Due to his familiarity among younger fans, some were left confused as to who he was, even after the mask came off. Ultimately, it just comes down to whether you’ve heard of someone or you haven’t.

9 Tree: Ana Gasteyer

Actress, comedian, and Saturday Night Live alum Ana Gasteyer was the celebrity under the Tree mask. Despite singing not being her primary profession, Gasteyer held her own to reach the final six in the competition. To reach this position, she defeated established singers such as Patti LaBelle and Michelle Williams of Destiny’s Child.

Throughout the season, Gasteyer also kept fans guessing regarding her identity with other theories including Paula Abdul, Rachael Ray, and Elvira. However, too many clues began to link back to the Mean Girls co-star for it not to be Gasteyer. As some fans later learned, Gasteyer does have professional singing experience by playing Elphaba in Wicked on Broadway.

8 Eagle: Dr. Drew Pinsky

Celebrity physician and former co-host of the radio show Loveline, Dr. Drew Pinsky was exposed as the performer hiding in the Eagle costume. Pinsky’s reveal threw a lot of people, including judges Ken Jeong and Jenny McCarthy. Both are friends of Pinsky’s who did not even bring his name up as a guess.

Fans were also surprised by the unmasking with earlier guesses for Eagle’s identity ranging from actor Aaron Paul to former Poison frontman Bret Michaels. The latter can possibly be attributed to Eagle’s rock attire and the song choice of “I’d Do Anything For Love (But I Won’t Do That)” by Meat Loaf in what ended up being his only non-SmackDown performance.

7 Black Widow: Raven-Symone

Disney Channel star and former The View panelist Raven-Symone was identified as Black Widow in week five of the competition. Her elimination came after suffering a broken arm between appearances on the show. Prior to The Masked Singer, there had been no indication that Symone planned to re-enter the world of music.  There was also excitement as Symone’s reveal was more confirmation of an unplanned reunion with one of her former co-stars, another masked celebrity on the show.

Similarly to Ninja, the inclusion of Symone also appealed to a certain generation who watched her show and films on Disney Channel while growing up.

6 Ladybug: Kelly Osbourne

British media personality, fashion designer, singer-songwriter and actress Kelly Osbourne was revealed as Ladybug in week six. While most fans had already surmised Osbourne being under the mask from the clues, her speaking voice confused both the judges and online detectives. Throughout her time on The Masked Singer, she had adopted a faux Southern accent to throw people off her scent.

While singing is not her main source of income nowadays, Osbourne went a respectable distance while on the show. Some of the songs she performed included “Holding Out For A Hero” by Bonnie Tyler, “Hit Me With Your Best Shot” by Pat Benatar and “Juice” by Lizzo.

5 Fox: Wayne Brady

Multi-hyphenate actor, comedian, singer and game show host, Wayne Brady was the season two winner, under the Fox mask. Prior to his appearance on The Masked Singer, Brady had actually been a guess for Monster during the previous season, who turned out to be T-Pain. Additionally, fans believed Brady to be hiding under a different season two mask; Thingamajig.

After being incorrectly suspected on multiple occasions, the very fact that Brady was on the show was as surprising, if not more so, than if he had not also been guessed as Fox. Which, from his first performance, he had been, by the way. Another Fox guess was Jamie Foxx… but that’s another story.

4 Thingamajig: Victor Oladipo

The man actually donning the unique Thingamajig costume was Victor Oladipo, an NBA star for the Indiana Pacers. Finishing just shy of the final, Oladipo’s impressive vocals came as a surprise when considering his day job as an athlete. From his first note, he outshone his nearest counterparts from the previous season, Terry Bradshaw and Antonio Brown.

Despite the initial confusion for Wayne Brady, Oladipo soon established himself as a performer with his own unique sound. Thingamajig also went on somewhat of an arc throughout the season, from his “romance” with Nicole Scherzinger to noticeably getting stronger and more confident vocally with each week.

3 Rottweiler: Chris Daughtry

The frontman of his self-named band and one-time American Idol contestant, Daughtry, as the Rottweiler, was the runner-up in season two of The Masked Singer. After denying he was under the canine mask, the finale exposed the truth. Like some of the other contestants, Daughtry was a guess in the first week after very specific clues for Rottweiler pointed to him as well as his recognizable vocals.

Aside from his unconvincing aversion, another reason why Daughtry being on The Masked Singer was so surprising had nothing to do with the show at all. It was the fact that he’d been on American Idol. Thirteen years after achieving a fourth-place finish on Idol, competing on another Fox singing competition, albeit a very unusual and unique show, was unexpected.

2 Flamingo: Adrienne Bailon

Former Cheetah Girls band member and now co-host of The Real, Adrienne Bailon scored a third-place finish on The Masked Singer as the fabulous Flamingo. As referred to earlier, Bailon’s appearance led to somewhat of a reunion with former bandmate/co-star Raven-Symone. While there were very talented performers in the second season, she managed to beat most of the competition and become the final woman standing.

When season two was filmed, Bailon had been hosting The Real for six years. Much like Symone, there had been no obvious imminent return to Bailon’s musical roots which made her participation a nice surprise for longtime fans once people realized Bailon was under the mask, weeks before she was actually revealed.

1 Leopard: Seal

Four-time Grammy Award winner Seal was the man behind the charismatic Leopard, who eventually finished in fourth place. Following his elimination in the semi-final, Seal revealed that he had done the show for his children, who were fans. Much like Joey Fatone (Rabbit) had done in season one, Seal disguised his mannerisms to fall in line with the flamboyant costume, prompting guesses such as RuPaul or Billy Porter.

While not an obvious choice based on stage presence alone, it was Seal’s distinctive vocal tone that clued most into his identity. Even still, some could not see past the Leopard’s characterization and ruled Seal out for that reason. Some of the songs performed by Seal/Leopard included “Somebody to Love” by Queen, “Respect” by Aretha Franklin and “Stitches” by Shawn Mendes.

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