âThe Masked Singerâ finale: Nick Lachey wins Season 5, while one lucky fan wins $100K By Stephanie Weaver FULL INTERVIEW: Nick Lachey wins Season 5 of The Masked Singer The Season Five winner underneath the Piglet costume was revealed as iconic singer Nick Lachey, famous for being in the 90s boy band 98 Degrees. LOS ANGELES - Black Swan, Piglet and Chameleon battled it out one last time in hopes to win the fifth season of "The Masked Singer", but only one contestant would go home with the coveted Golden Mask Trophy. "I could absolutely see you taking home the Golden Mask, Piglet," panelist Jenny McCarthy said Wednesday after Piglet’s rendition of "Faithfully" by Journey.