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Feb 28, 2019 · T-Pain Wins 'The Masked Singer,' Followed By Donny Osmond And Gladys Knight. The Florida rapper, who masqueraded as the Monster over the course of the show, capped off the competition with a performance of Montell Jordan's 1995 classic "This Is How We Do It". Rachel Brodsky. | GRAMMYs / Feb 28, 2019 - 12:27 pm.
Feb 28, 2019 · After much mounting anticipation — and being crowned the winner — the monster’s identity was revealed: Grammy Award-winning singer and rapper T-Pain was behind the mask!
Mar 2, 2019 · The performer took off his Monster mask and was crowned the first-ever winner of the Fox reality show on Wednesday, in a moment that saw both the panel, and T-Pain himself, getting emotional.