Reality television runs the gamut from cooking shows to shows about finding love to flamboyant housewives. Each week, viewers eat up reality television and the regular people who have become stars. While some shows are all about conflict and drama, others are all about competition. One popular competition-based reality show is “The Masked Singer.” The show is a singing competition with a twist. Each contestant is a known public figure, either an athlete, actor, singer, talk show host, or other public figure who gets to show their range and sing cover songs. The thing that makes this show unique is that the contestant wears elaborate costumes to hide their identity, so they are judged on their performance alone.
Throughout each episode, audience members and a panel of celebrity judges vote, and contestants are eliminated one by one. When they are eliminated, they get to remove the mask. Throughout the show clues are revealed about the contestants’ identities to help the audience, and judges narrow down their guesses. While it may seem like an odd formula for a reality show, viewers love it, and the show is currently in its 11th season.
The celebrities and cover songs give the show a fun, upbeat vibe, but the real star of the show is the elaborate costumes, which are so well thought out and creatively put together that Marina Toybina, the costume designer for the first six seasons of the show, won a Costume Designers Guild Award and two Creative Arts Emmy Awards. If you have never seen the show, we will catch you up on every winner of “The Masked Singer” and what they are doing now. (If you can’t get enough of reality television, check out “Every Winner of Master Chef and WhereAre They Now.”)
1. Season 1 Monster – T-Pain
The first season of the show started it all with a mix of celebrity contests like actors Tori Spelling and Terry Bradshaw, singers LaToya Jackson and Gladys Knight, and comics Margaret Cho and Tommy Chong, just to name a few. The costumes ranged from Spelling’s Unicorn to Chong’s Pineapple to Knight’s Alien. But in the end, rapper T-Pain, dressed as a Monster, won the show. T-Pain is a rapper, songwriter, and record producer. After his win, T-Pain continued to write and make music. During an interview with Billboard, the talented artist talked about ghostwriting music for other artists in genres outside of hip-hop.
2. Season 2 Fox – Wayne Brady
After the fun of season one, fans became loyal viewers, and “The Masked Singer” went even bigger with celebrity contestants like Michelle Williams, Seal, Patti LaBelle, Kelli Osborne, Dr. Drew, and Raven Simone, to name a few. But the winner of season two was actor Wayne Brady. Brady was dressed as a Fox for his win, and one of his clues mentioned he had worked with actors from Doogie to Doubtfire, hinting at his role as Barny’s brother on the long-running series, “How I Met Your Mother” and his role in the iconic Robin Williams’ film “Mrs. Doubtfire.” Wayne Brady currently hosts the game show “Let’s Make a Deal,” which has earned him three Emmy nominations for best host.
3. Season 3 Knight Angel – Kandi Burress
In season three, the show had some great costumes ranging from a Taco to a T-rex to a Turtle. The celebrities this time around were an eclectic mix of performers and one politician. Some of the well-known figures in this season were Bret Michales, Sarah Palin, Chaka Khan, Dionne Warwick, and Lil Wayne. The singer and star of “The Housewives of Atlanta,” Kandi Burress, was the winner. After her win, the talented performer returned to the reality television Housewives franchise and recently won The People’s Choice Award for the Reality TV Star of the Year.
4. Season 4 Sun – LeAnn Rhymes
LAS VEGAS - MAY 21: Musician Leann Rhymes and her husband Dean Sheremet attend the 38th Annual Country Music Awards held at the Mandalay Bay Hotel and Casino on May 21st, 2003 in Las Vegas, Nevada. (Photo by Robert Mora/Getty Images)
In the fourth season, the show welcomed seasoned performers like Bob Saget, Busta Rhymes, Wendy Williams, Micky Rourke, and other less well-known faces. But the star of season four was country singer and performer LeeAnn Rhymes. Rhymes dressed as the Sun, and she really did shine. The popular singer continues to write music and has acted in a few small film roles. This season, the costumes took some bold swings with interesting choices like a Whatchamacallit, Squiggly Monster, and Gremlin.
5. Season 5 Piglet – Nick Lachey
LAS VEGAS, NEVADA - FEBRUARY 10: (L-R) Nick Lachey and Vanessa Lachey attend Michael Rubin's Fanatics Super Bowl party at the Marquee Nightclub at The Cosmopolitan of Las Vegas on February 10, 2024 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
Season five winner Nick Lachey is not new to the music business or reality television. He famously starred with his ex-wife Jessica Simpson in “The Newlyweds,” which aired on MTV from 2003 to 2005. After winning season five, Lachey hosted two reality shows, “The Ultimatum: Marry or Move On” and “Perfect Match.”
6. Season 6 Queen of Hearts – Jewel
CINCINNATI, OHIO - AUGUST 21: Jewel speak during Mental Health in the Workplace on the Inspire Lounge stage during the second day of The Wellness Experience by Kroger at The Banks on August 21, 2021 in Cincinnati, Ohio. (Photo by Duane Prokop/Getty Images for The Wellness Experience by Kroger)
From living in her car in Alaska to winning Season Six of “The Masked Singer,” singer-songwriter Jewel has come a long way. The singer, so famous she only needs one name, wore a Queen of Hearts costume and dominated her season six competitors, Toni Braxton, Tyga, Johnny Rotten, Faith Evans, and Natasha Bedingfield. Since her win, Jewel has continued to delight audiences with her distinct voice and music. This season, two duos, a married couple, Katherine McPhee and David Foster, were dressed as a Banana Split. And mother-daughter duo Mama June and Honey Boo Boo, who dressed as a Beach Ball.
7. Season 7 Firefly – Teyana Taylor
Firefly, Teyana Taylor lit up the stage in season seven, and she really was on fire. Taylor won season seven and beat out names like Cheyenne Jackson, En Vogue, Shaggy, Jennifer Holliday, and Christie Brinkley. She almost lost in episode two but managed to hang in there the entire season and win. Taylor has been busy ever since she won the show acting in films. In 2023, “White Men Can’t Jump” and “The Book of Clarence” were released.
This season saw another duo the magicians, Penn and Teller. The magical men sang “Hey Soul Sister “by Train and “Sharp Dressed Man”by ZZ Top. Their unique costume, Hydra, had some limitations, and they had to be wheeled out on set.
One thing that set this season apart was that it saw a bit of controversy, as the contestant wearing a Jack in the Box costume was revealed to be a failed politician, Rudy Guliana. This led the regular judge, Ken Jeong, to storm off the set to protest the casting choice.
8. Season 8 Harp – Amber Riley
The season eight winner is not new to singing competitions actor and singer Amber Riley. Riley was a regular in the teen drama/comedy “Glee,” which followed a group of high schoolers trying to win high school singing competitions at regional and national levels. Riley dressed as a Harp and sang “Perfect” by Pink and “Thank You for Being a Friend” from The Golden Girls. But she really blew away the competition with “About Damn Time” by Lizzo. Her runner-up was the female 90s duo Wilson Phillips. Other celebrities in this season were George Clinton, Gloria Gaynor, William Shatner, Nikki Glaser, and Adam Corolla. Riley continues to perform and is currently in a stage production of “A Preacher’s Wife.”
9. Season 9 Medusa – Bishop Briggs
Don’t look directly at Medusa season nine’s winner, or you will turn to stone. Bishop Briggs wore an extravagant Medusa costume as she sang her heart out and won season nine. Bishop grew up in Tokyo and Hong Kong and was inspired by singing karaoke with friends to pursue music as a career. She is the show’s youngest winner and, in 2023, released her EP, “When Everything Went Dark.”
Bishop had stiff competition in season nine with competitors like Michael Bolton, Debbie Gibson, David Archuleta, Howie Mandel, Sara Evans, and Dee Snider. This season had another first: the acapella group Pentatonix was a contestant and performed dressed as a California Roll.
10. Season 10 Cow – Ne-Yo
The cow jumped over the moon, and the season ten competition. Singer Ne-Yo won season ten, all while dressed as a cud-chewing heifer. He wowed the crowd with Justin Timberlake’s “Cry Me a River” and Janet Jackson’s “Rhythm Nation.”Ne-Yo is a singer and songwriter currently acting in “BMF,” an American crime drama on the Starz network. His competitors in season ten were Macy, Gray, John Oats, Keysheia Cole, Anthony Anderson, and Michael Rapaport.