Contestants On The Masked Singer Who Surprised Me

Hello everyone!


Here I am with another blog post about The Masked Singer!

As you’re probably all aware, the show has had many amazing performances over the course of thirteen seasons from many amazing contestants, but sometimes the amazing performances come from contestants you wouldn’t expect to give amazing performances, or the performance is from a celebrity you wouldn’t expect to see on the show, and that’s where this blog post comes in. 

Today, I am going to share with you all the contestants that surprised me with how good they were or that they were even on the show. I will explain how they surprised me, and also what was so great about them. 

So, with that out of the way, let’s get started!

The first celebrity that I feel could be described as surprisingly talented is Victor Oladipo. For those of you who don’t know who that is, he is a basketball player who has played for several teams and is currently a sports analyst for ESPN. As my knowledge of celebrities is very limited, especially athletes, I had no idea that he had already done some singing and put out some music, so imagine hearing an amazing performance of Rainbow by Kacey Musgraves, and then finding out that this amazing singer is actually a basketball player, you would definitely be surprised. But frankly, Victor Oladipo is an amazing singer, and if you want more proof, he managed to beat professional singer Michelle Williams in one episode. I hope that he puts out more music in the future once he officially retires from basketball.

The next celebrity that surprised me with how talented they were was Ana Gasteyer, who is best known for being a cast member on Saturday Night Live. Before The Masked Singer, my only experience with her was on Match Game, so I didn’t know much about her. So imagine my shock when I found out that she has been on Broadway several times and is also an amazing singer, with her performance of Think by Aretha Franklin being one of the best of the season. But that’s the show for you. It shines a spotlight on the singers you have probably forgotten about and the celebrities you didn’t know could sing.

The next celebrity that surprised me was Drew Carey, who is best known for being a comedian and TV host. While he wasn’t an amazing singer, I was still impressed by how well he performed She Bangs by Ricky Martin and It’s Not Unusual by Tom Jones. Also yes, you read that correctly. Drew Carey performed She Bangs by Ricky Martin. Sometimes they have celebrities who are just there to be funny.

The next celebrity that surprised me was Tony Hawk. Yes, that Tony Hawk. The Skateboarder. While he was only on one episode, I was really impressed by his performance of Friday I’m In Love by The Cure. He did a great job at sounding like the original song.

The next celebrity that surprised me was Tom Bergeron, best known for being the former host of America’s Funniest Home Videos and Dancing With The Stars. I was impressed by all three of his performances, especially his performance of Fly Me To The Moon by Frank Sinatra, and if you want to know how good he was, he managed to last longer than living legend Dionne Warwick.

The next celebrity that surprised me was Jordyn Woods. For those of you who have no idea who that is, let me take you back in time to a magical year known as 2019, when a socialite and model named Jordyn Woods was best friends with Kylie Jenner until February of that year, when it was discovered that she had been involved with Khloe Kardashian’s boyfriend Tristan Thompson. So I have just shared with you all her biggest claim to fame, and she hasn’t done that much since, or even really appeared on that many TV shows, since, and this is my way of saying that she is a really great singer. I’m being serious, her performance of Dancing On My Own by Robyn was one of the most powerful performances that season, and if she wanted to put out any music in the future, I think that would be a great idea.

The next celebrity that surprised me was Barry Zito. He is yet another example of an athlete showing off that they can sing, as he is a former baseball player, and he gave several great performances, with my favorite being his performance of Humble and Kind by Tim McGraw.

The next celebrity that surprised me was Dr. Elvis Francois. For those of you who have no idea who that is, which I imagine is all of you reading, he is an orthopedic surgeon and an amateur singer known for making viral videos of him singing before and during the pandemic. So I just shared with you all what makes him famous, which is that he is a surgeon who put out some viral videos of himself singing at one point in time, and he is proof that sometimes your career does not give you any limitations on what else you can do, as he is an amazing singer, and I think that he did a great job showing off all the power he has in his voice in all three of his performances.

The next celebrity that surprised me was Paul Anka. This one has nothing to do with his singing ability, and everything to do with the fact that I’m surprised the producers on the show even thought of him, as he is a singer and songwriter who got his start in the 1950s. Yes, you read that correctly, the 1950s, one of the earliest starts of any contestant on the show. And he also worked with Frank Sinatra. But that’s also kind of why I liked him being on the show, as he has had such a long and kind of legendary career, and he was a good singer.

The next celebrity that surprised me was Chloe Kim, who is a snowboarder. The show has had many athletes as contestants, and I’m just going to say this right now, Chloe Kim is one of the best athlete contestants the show has ever had. Her performances of Crazy by Patsy Cline and Stay by Rihanna and Mikky Ekko were amazing, and in one episode, she managed to make it to The Semi-Finals before Paul Anka or Aloe Blacc could, and she absolutely deserved it. And I am being completely serious when I say this, when she retires from her snowboarding career, she should release some music.

The next celebrity who surprised me was Rob Schneider, best known for being on Saturday Night Live and his various appearances in Adam Sandler movies. Typically when the show has comedians as contestants, they can range from being pretty good to someone who should never be allowed to sing again. Rob Schneider is one of the few exceptions, as he is surprisingly a very good singer, and he gave three great performances where he managed to sound like Roy Orbison while singing Oh, Pretty Woman, sound like Elvis while singing the Elvis inspired Crazy Little Thing Called Love by Queen, and he also performed Sabor a Mi by Luis Miguel, a song that is entirely in Spanish.

The next celebrity who surprised me was Johnny Rotten, the former lead singer of The Sex Pistols. While I wasn’t surprised by his singing abilities, I was more surprised by the fact that Johnny Rotten from The Sex Pistols was a contestant on The Masked Singer, as to me, he seems like the kind of guy who would not only turn down being on the show, he would also go out of his way to see the producers and literally say “No” right to their faces. But he was on the show, and I’m so glad that he was, because he was very good and it led to a fun moment with the panelists being shocked by Johnny Rotten being on the show.

The next celebrity that surprised me was Willie Robertson from Duck Dynasty. If you had asked me before the show if I thought Willie Robertson would be a good singer, I would have laughed and said that he definitely wasn’t, but I was surprised to find out that he is a very good singer who can pull off several country songs, and it would not surprise me if he put out some country music in the future.

The next celebrity that surprised me was Bobby Berk. For those of you who don’t know who that is, he is an interior designer and one of the hosts of Queer Eye. So here’s a little backstory for you. His costume, The Caterpillar, was hyped up on the show’s official podcast by one of the people who worked on the show as being one of the best that season, and also for being someone who was shockingly talented that came out of left field, his words, not mine. He could not have been more right, because Bobby Berk was amazing, and he performed three songs on the show, which were If I Were A Boy by Beyonce, It’s Gonna Be Me by NSYNC, and Friends In Low Places by Garth Brooks, which are three incredibly different songs, and he did amazing on all three of them. I feel that he would be completely justified if he chose to put out an album in the future.

The next celebrity that surprised me was Mario Cantone, who is best known for for starring in Sex And The City and for being a frequent panelist on Match Game. During his appearances on Match Game, I learned that he had some Broadway experience, so I knew that he had some singing experience, but I had no idea just how great he was until he was on The Masked Singer. He only had one performance due to the format of the season, and it was on Andrew Lloyd Webber Night, and his performance was so great that Andrew Lloyd Webber himself said that he would hire him to be in one of his shows. Mario Cantone is also one of the few contestants that I would say got unfairly treated by the one celebrity moves on at the end format, and if the show chose to bring him back for a second chance, I would be okay with that. 

The next celebrity that surprised me was Nikki Glaser, who is best known for being a comedian, actress, and TV host. Much like with Rob Schneider, she is another comedian that you might not expect anything from, but you would be wrong, because she gave some great performances, with her performance of Thinking Of You by Katy Perry being one of my favorites of hers.

The next celebrity that surprised me was Dee Snider, the lead singer of Twisted Sister. Yes, I realize that he is already a singer, so him being a good singer should not be a surprise, but what did surprise me was that he showed he has range, as I found his performance of Don’t You (Forget About Me) by Simple Minds to be great, and showed a different side to his voice, which is a quieter and less aggressive tone, only raising his voice in times when it was appropriate in the song.

The next celebrity that surprised me was Alicia Witt. For those of you who don’t know who she is, which I imagine is everyone reading, she is an actress and singer known for her roles in movies like Dune from 1984, and shows like Twin Peaks, Cybill, Nashville, and Orange Is The New Black. What surprised me about her was the fact that at the time of the show originally airing, I had no idea who she was, and even right now I still am not sure of who she is and what she is famous for, which almost makes me appreciate her more, because I can just focus on her performances without really knowing who she is, and she gave two great performances of Over The Rainbow and Starlight by Muse, the latter of which also had her either playing piano during it or she was doing an amazing job at pretending to do so.

The next celebrity who surprised me was Lou Diamond Phillips, who is best known for playing Richie Valens in the movie La Bamba. One of the best things about the show is that it will highlight celebrities that you probably didn’t know have done some singing in the past, so imagine my surprise in finding out that not only has Lou Diamond Phillips done singing in the past, he was nominated for a Tony Award for his portrayal of King Mongkut of Siam in The King and I. And he certainly could sing, as he managed to completely change his voice in his second performance, which was also in his first episode, did a great job at sounding like one of the Davies brothers when he was singing You Really Got Me by The Kinks, and gave quite possibly the best unmasked encore performance of the entire show by performing La Bamba.

The next celebrity who surprised me was Keenan Allen, who is a wide receiver for the Los Angeles Chargers. He is yet another example of an athlete showing off their amazing singing abilities, as when his first performance of One Call Away by Charlie Puth dropped hours before the episode premiered, I was convinced that he was a singer, so imagine my surprise when I saw the clue package for the first time and saw a ton of football references.

The next celebrity who surprised me was Olivia Culpo, who is best known for being a model who won Miss Universe. I was really impressed by her beautiful performance of Yellow by Coldplay, and her performance of Stargazing by Kygo and Justin Jesso was also great.

The next celebrity who surprised me was Bishop Briggs, who is a singer best known for her song River. You’re probably wondering how someone who is a singer could surprise me, and the answer is simple. All I knew about her before the show was her song River, and even then it was from Jewel’s performance of the song in Season 6, so I had never really heard Bishop Briggs sing before, and when I first heard her perform on the first episode of Season 9, I was so amazed and literally got chills. I am so glad that the show introduced me to such an amazing singer.

The next celebrity who surprised me was Anthony Anderson from Black-ish. While he was not the best contestant the show has ever had, he was surprisingly pretty good, and gave an entertaining performance of Come On Eileen by Dexy’s Midnight Runners.

The next celebrity who surprised me was Tom Sandoval from Vanderpump Rules. Yes, I know that a lot of you reading this probably hate him, I understand, but hear me out. He is a very good singer, and his first performance was both great and incredibly brave, as it takes a lot of courage to sing a song originally performed by Steve Perry, but he did that by singing Any Way You Want It.

The next celebrity who surprised me was Tyler Posey from Teen Wolf. He only had two performances, which were Saturday Night’s Alright (For Fighting) by Elton John and Every Little Thing She Does Is Magic by The Police, but he performed them in a sort of Green Day/Bowling For Soup type of way that actually worked for both songs.

The next celebrity who surprised me was Ashley Parker Angel from O-Town. This one has nothing to do with his singing ability, and instead has to do with the fact that he was even on the show at a time when he has retired from the music industry to be a life coach. I’m glad that he was a contestant, as it seemed like his way of giving one final performance for his fans.

The next celebrity who surprised me was Sebastian Bach, the former lead singer of Skid Row. Yes, he is also a singer, but I have associated him with being a screaming heavy metal singer, but he did a great job showing off a slightly less aggressive side to his voice with his performances of Goodbye Yellow Brick Road by Elton John, Magic by Pilot, and I Was Made For Loving You by Kiss.

The next celebrity who surprised me was John Oates from Hall & Oates. Yes, I know he is a singer and is a member of one of the most famous duos of all time, but the reality is that Daryl Hall did basically all the singing in their songs, so this was a great way for some people to hear John Oates sing for maybe the first time, and he did an amazing job singing Walking In Memphis by Marc Cohn, and he also did a great job working with his Anteater costume, which had long arms that could barely move.

The next celebrity who surprised me was Janel Parrish, an actress and singer best known for playing Mona on Pretty Little Liars. She is another celebrity that I was unfamiliar with before she was on the show, and I’m glad the show introduced me to her, because she is a great singer, and she gave amazing performances of Uninvited by Alanis Morissette, The One That Got Away by Katy Perry, and Chasing Cars by Snow Patrol, and I think it would be great if she released more music.

The next celebrity who surprised me was John Schneider from The Dukes Of Hazzard. Before he was on the show, I knew that he was also a singer, but I had no idea just how great he was, as he gave several amazing and powerful performances during his time on the show, such as Hooked On A Feeling by Blue Swede and Georgia On My Mind by Ray Charles.

The next celebrity who surprised me was Joe Bastianich, who is a restaurateur and a judge on the show MasterChef. I knew that he had started a small music career in recent years, but I had no idea what his singing even sounded like, or if he was even good. When he was on the show, I found out that he was actually very good, and he gave an amazing performance of Only The Good Die Young by Billy Joel.

The next celebrity who surprised me was Colton Underwood from The Bachelor Universe. Reality stars on The Masked Singer are very hit or miss, as some of them are really great, while some of them are among the worst contestants the show has ever had. Colton Underwood was surprisingly good, as he had two great performances of Home by Phillip Phillips and All That You Are by Goo Goo Dolls.

The next celebrity who surprised me was DeMarcus Ware, who is a former NFL player. The show has had many athletes as contestants in the past, and much like with reality stars, they can either be great or really bad, and the best ones are typically athletes who have already done some singing at some point in their careers. DeMarcus Ware is a special case though, as to my knowledge, he has not done much singing yet in his career except for singing the National Anthem, and despite having only one performance, he did an amazing job singing Everybody Wants To Rule The World by Tears For Fears.

The next celebrity who surprised me was Kate Flannery from The Office. I knew that she had gone on tour with Jane Lynch in the past around the holidays where they have performed holiday songs, but I had never heard her sing before. The Masked Singer was the first time I had heard Kate Flannery sing, and she was great, giving a great performance of Material Girl by Madonna, a powerful performance of 21 Guns by Green Day, and one of the bravest performances of the entire series, as she performed Under Pressure, a song that is originally sung by Freddie Mercury and David Bowie. 

The next celebrity who surprised me was Chrissy Metz, who is best known for starring in This Is Us. I did not know that she had ever done any singing before she was on the show, so it was nice to hear that she is a great singer with a beautiful voice, with two of her best performances being Just The Way You Are by Billy Joel and The House That Built Me by Miranda Lambert.

The next celebrity who surprised me was Thelma Houston, a disco singer who is best known for her song Don’t Leave Me This Way. I had never even heard of her before she was on the show, and when I first hear her singing Piano Man, I was amazed by her voice, and my parents even initially thought that she was Bette Midler. I am also impressed by how her voice sounds, as at the time of the show, she was either in her late 70s or early 80s, and her voice was still incredibly strong in all of her performances.

The next celebrity who surprised me was Scott Porter, an actor best known for starring in the shows Friday Night Lights, Hart of Dixie, and Ginny & Georgia. Before he was on the show, I barely knew who he was, as the only place I had ever seen him before was on one episode of Whose Line Is It Anyway, and the only reason he was there was because the show would like to have guests from other shows on The CW. When he was on The Masked Singer, I could not have been more amazed by his singing ability, as he performed the widest variety of songs and artists, hit some impressive high notes, and in one of the most shocking revelations on the show, he admitted that he had no vocal training in his life, which is incredible because his voice is amazing. 

The next celebrity who surprised me was Paula Cole, a singer best known for her songs Where Have All The Cowboys Gone and I Don’t Want To Wait. She is another singer who I was not familiar with before she was on the show, but when I first heard her sing Pompeii by Bastille, I was amazed by what I heard, as she had taken the song and reworked it for her voice, and made it sound even better, so I was surprised both by how great she is and how much better the song became.

The next celebrity who surprised me was Kobie Turner, a football player who is the defensive end for The Los Angeles Rams. I am just going to say this right now. If you had played for me his first performance of Lose Control by Teddy Swims without giving me any idea as to who was underneath the costume, I am positive I would have said that it was a singer. That’s how great he was. And he also gave amazing performances of Miss Independent by Ne-Yo, House Of The Rising Sun by The Animals, and Iris by The Goo Goo Dolls. If you want to be more impressed by him, he managed to beat out Natalie Imbruglia, a professional singer, in the Group B Finals. If you’re wondering why he is so great at singing, it is because he ran three A cappella groups while in high school. I also feel that when he retires from football, he should release some music.

The next celebrity who surprised me was Aubrey O’Day from Danity Kane. How she surprised me is very interesting though, as I knew she was a singer, and her first two performances of Just Give Me A Reason by P!nk and Nate Ruess and Wide Awake by Katy Perry were both great and powerful, but she surprised me with her third episode, where rather than going subtle and emotional, she really just showed off all the power and energy in her voice. She showed so much energy that even though all three contestants that night were great, I was convinced that she would make it to the Final Six, so I was shocked when she didn’t.

The next celebrity who surprised me was James Van Der Beek, who is best known for starring in Dawson’s Creek and Varsity Blues. I had actually heard him sing before he was a contestant, as he was on an episode of the show We Are Family, where he sang some of I Hope You Dance by Lee Ann Womack, but this time he was giving full performances, and he was great at all of them, such as a musical theatre worthy performance of Rewrite The Stars from The Greatest Showman and a slowed down version of Disturbia by Rihanna that almost felt like a completely different song.

The next celebrity who surprised me was 90s star Matthew Lawrence, best known for starring in Boy Meets World and Mrs. Doubtfire. Before he was on the show, I found out through Wikipedia that he had done some singing in the past, but I didn’t know how much he had really done, and in his clue package, he said that he had never performed in front of an audience before and was terrified. However, I feel that he did an amazing job on the show, as his performance of Hallelujah by Leonard Cohen was incredibly powerful and moving, and his performance of That’s Amore by Dean Martin showed how much range he really has, and he also sounded like he could pass as a member of the Rat Pack.

The next celebrity who surprised me was Meg Donnelly, who is an actress and singer best known for starring in the show American Housewife and the Zombies movie series. I did know that she could sing before she was on the show, as I had seen her perform as part of the Disney Parks Holiday Parade before, but I could not remember how her singing was, so when she was on the show, I was very impressed by how great she was at performing both slower ballads and 2000s pop songs. I really hope that her time on this show and her upcoming Broadway debut serves as a starting point for her music career.

The next celebrity who surprised me was Edwin McCain, an alternative rock singer best known for his song I’ll Be. Much like many of the other celebrities in this post, I had never heard of him, so the show was my introduction to him, and I was impressed by how great he is at singing, so much so to the point that when I first heard him singing, I honestly thought he was Steve Perry from Journey.

The last celebrity who surprised me was Brian Kelley, one of the former members of Florida Georgia Line. I am going to let you all in on a secret right now: I am not a fan of country. It genuinely sounds like the same song every time, and I can’t tell any singers apart when I hear their voices. When Brian Kelley was on the show, however, I was impressed by how he did, as he gave amazing performances of a wide variety of songs, such as Unwell by Matchbox Twenty, I Swear by All-4-One, Love Yourself by Justin Bieber, There’s Nothing Holdin’ Me Back by Shawn Mendes, The Scientist by Coldplay, A Bar Song (Tipsy) by Shaboozey, and Stay by Sugarland. He managed to be the first country singer I enjoyed listening to, and I hope that his time on the show did a great job in helping him establish his solo career.

Overall, these are all the celebrities that have surprised me through the course of the show! I hope you all enjoyed reading this blog post, and I’ll see you all soon with another one!