Season 6 of Fox’s runaway hit game show competition The Masked Singer will enjoy a two-night premiere this fall. As fans of the series look ahead to the newest collection of disguised crooners, it’s worth taking stock of how far the show has come in its first five seasons and who has emerged victorious.
Merging multigenerational singing talent from all musical genres, The Masked Singer has featured some of the most famous and iconic musical artists from the past and present. While it’s difficult to guess the identities of the costumed singers by their voices alone, it’s not hard to see why the winners and runners-up found so much success on the show.
Season 1: Winner – T-Pain, Runner-Up – Donnie Osmond
The riveting first season of The Masked Singer saw the legendary Gladys Knight finish in third place behind runner-up Donnie Osmond and eventual surprise Masked Singer winner T-Pain. Dressed as Peacock, Osmond won his first duel while being voted “safe” for the next four of seven weeks. The 1970s music star had standout performances by singing John Legend’s “All of Me” and The Weeknd’s “Can’t Feel My Face.”
Disguised in one of the best Masked Singer costumes as Monster, rapper T-Pain stunned audiences with his soulful, non-auto-tuned versions of Sam Smith’s “Stay With Me,” Lenny Kravitz’s “American Woman” and his final winning performance of Montell Jordan’s “This Is How We Do it.” T-Pain not only tricked the viewers, but he also showed tremendous vocal range across a series of musical genres that helped him triumph in the end.
Season 2: Winner – Wayne Brady, Runner-Up – Chris Daughtry
Season 2 saw an intense singing performance battle between Fox (Wayne Brady) and Rottweiler (Chris Daughtry), the final two contestants who bested such legendary singers as Seal, Patti LaBelle, Michelle Williams, and others. In the end, the multitalented stage-and-screen performer Wayne Brady took home the trophy by crushing his renditions of Maroon 5’s “This Love” and Bobby Brown’s “Every Little Step,” among others.
Professional singer Chris Daughtry put up a valiant fight by singing contemporary pop hits like Bruno Mars’ “Grenade” and Ed Sheeran’s “Castle on the Hill.” In a heated mirror match, both men scored a pair of head-to-head wins and four “safe” votes during their time on the show. However, Brady’s version of Otis Redding’s “Try a Little Tenderness” blew Daughtry’s version of Sia’s “Alive” out of the water in the finale, earning him the gold.
Season 3: Winner – Kandi Burruss, Runner-Up – Jesse McCartney
Season 3 featured one of the most evenly matched final two contestants, both of whom call singing their profession. Moreover, both Kandi Burruss and Jesse McCartney won their week 11 head-to-head dual in addition to being voted “safe” a whopping seven times each. Dressed as Night Angel, Burruss ultimately prevailed with her showstopping performance of Tina Turner’s “River Deep, Mountain High” in the finale.
Giving her a serious run for her money, Jesse McCartney kept his voice shrouded as a Turtle, delivering standout renditions of Coldplay’s “Fix You,” Steve Winwood’s “Higher Love,” and Seal’s “Kiss From a Rose” before finally falling short with Lewis Capaldi’s “Before You Go.” Both Burruss and McCartney bested such famous celebrity contestants as Dionne Warwick and Chaka Khan en route to finishing in first and second place.
Season 4: Winner – LeAnn Rimes, Runner-Up – Aloe Blacc
In a lineup loaded with talent, Season 4 saw six professional singers among the seven finalists. In the end, longtime country star LeAnn Rimes bested rapper-turned-crooner Aloe Blacc in part by becoming the only contestant to win more than one head-to-head showdown. Rimes appeared in a Sun costume while Blacc dressed as a Mushroom.
Rimes and Blacc prevailed over a slate of talented singers such as Nick Carter, Paul Anka, Tori Kelly, Taylor Dane, Clint Black, and others to face off in a dramatic showdown during the finale. Blacc became a frontrunner after his scintillating performances of Cher’s “If I Could Turn Back Time,” Amy Winehouse’s “Valerie,” and a soulful version of Steve Wonder’s “I Wish” in the finale. Unfortunately, Blacc was overshadowed by Rimes’ final performance of Brandi Carlile’s “The Story,” her third winning song after Janis Joplin’s “Piece of My Heart” in week 7 and Billie Eilish’s “When The Party’s Over” in week 10.
Season 5: Winner – Nick Lachey, Runner-Up – JoJo
The fifth and most recent season of The Masked Singer featured an epic battle of singing supremacy between former boy-bander Nick Lachey and current pop sensation JoJo. When the dust settled, Lachey emerged victorious in his Piglet costume. Aside from their final performances, standouts include Lachey’s versions of Stevie Wonder’s “Superstition” and Phil Collins’ “Against All Odds,” and JoJo’s rendition of Ed Sheeran’s “Thinking Out Loud” and Stevie Wonder’s “Do I Do.”
With identical scorecards prior to the finale, Lachey and JoJo (dressed as Black Swan) both scored “safe” votes in weeks 2, 4, 5, 7,9, 10, and 11. In as tight a race as could be, the 98 Degrees alumnus turned up the heat and separated himself from his chief rival in the finale by belting out Journey’s “Faithfully.” While Wiz Khalifa came on strong in the end as the Chameleon, JoJo managed to become runner-up by singing Michael Bolton’s “How Am I Supposed To Live Without You.” Both Lachey and JoJo outlasted some of the stiffest competition in the series’ history, including Omarion, Bobby Brown, Hanson, Tyrese Gibson, and more.
