‘The Masked Singer’ names Top 5 best performances ever: T-Pain, Donny Osmond …

Marcus James Dixon
·3 min read
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“Over 150 mystery celebrities have performed 523 songs in front of our panel, and tonight we’re showcasing five of the best and most beloved performances of all time,” Nick Cannon proclaimed at the start of “The Masked Singer” Season 10 premiere. Throughout the hour-long episode on Sunday, September 10, the host threw back to the handful of musical moments that still stick with viewers all these years later. Read on for “The Masked Singer’s” Top 5 best performances ever.

In addition to Nick, the four regular judges are also back this year as the celebrity sleuths/panelists: Robin Thicke, Jenny McCarthy Wahlberg, Ken Jeong and Nicole Scherzinger. Each week they analyze the clues on Fox’s reality TV show and make their best guesses as to which famous faces might be hiding beneath the extravagant costumes. For four of the five all-time top performers below, at least one of the judges ultimately guessed the contestant’s identity. The singer that stumped them all was T-Pain, the winner of Season 1, who was dressed as a friendly, one-eyed monster.

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5. Peacock singing “The Greatest Show” in Season 1
Celebrity: Donny Osmond
Airdate: January 2, 2019

This American icon and former teen idol wasn’t afraid to “Shake a Tail Feather” as he rocked the house to hit songs, including the anthem from the movie “The Greatest Showman.” Donny Osmond managed to sing his way to second place in the first season of “The Masked Singer” while befuddling all but one judge (Jenny).

4. Sun singing “Cuz I Love You” in Season 4
Celebrity: LeAnn Rimes
Airdate: September 23, 2020

How fitting that Sun won the Golden Mask — after all, this shining star was the first contestant to perform this fourth season and set the bar extremely high with her “Cuz I Love You” cover. Throughout the competition the panelists threw out all kinds of guesses, but in the end both Jenny and Nicole guessed Sun was actually child singer LeAnn Rimes.

3. Thingamajig singing “Rainbow” in Season 2
Celebrity: Victor Oladipo
Airdate: October 16, 2019

This NBA All-Star showed off his hidden musical talents on “The Masked Singer” and developed a flirtatious relationship with Nicole, who he brought to tears with his vocal abilities. Perhaps more shocking than Victor Oladipo’s voice was the fact that Ken was the only judge to guess his true identity following a performance of “Winter Wonderland” by Bing Crosby.

2. Seahorse singing “My Heart Will Go On” in Season 4
Celebrity: Tori Kelly
Airdate: October 14, 2020

All of the clues about previously appearing on a singing competition show are what convinced Robin and Nicole to name this former “American Idol” contestant as their final pick. “I feel more like an entertainer now,” Tori Kelly proclaimed after being unmasked as the colorful Seahorse.

1. Monster singing “Stay With Me” in Season 1
Celebrity: T-Pain
Airdate: February 20, 2019

This chart-topping rapper and hit-making producer made history as the first winner of “The Masked Singer.” As the Monster, T-Pain was able to put his singing prowess at the forefront while keeping his identity hidden until the very end. Unfortunately, none of the judges were able to correctly pinpoint his true persona.

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