(March 1, 2019: Spoiler alert, this article contains revealing details about the hit Fox TV singing competition “The Masked Singer.”)

Musically speaking, the singer (and sometimes rapper) who used to refer to himself as “Teddy Pinned-Her-Ass-Down” – that name being an amalgamation of his own moniker T-Pain, the late soul singer Teddy Pendergrass, and just plain goofiness – hasn’t won much of anything lately.  

Singer T-Pain and his popular alter-ego “Monster,” the winner of the first season of “The Masked Singer”

At least not since his ‘00s and early ‘10s heyday when he was churning out Auto-Tune-enhanced bumpers like the 2007 No. 1 smash “Buy U A Drank (Shawty Snappin’)” and its followup “Bartender,” plus chart-topping hits with other artists, including “Kiss Kiss” with Chris Brown, “Low” with Flo Rida, and “Blame It” with Jamie Foxx, among others.

Since that time, T-Pain has been mostly silent on the Billboard charts and on the receiving end of a lot of jokes (or more accurately, the blame) for helping to popularize Auto-Tune, the vocal-enhancement technology that has dominated pop and hip-hop music for the better part of this decade (no disrespect to Cher, the ageless wonder who first popularized it with her 1999 No. 1 hit “Believe”).

So there was a bit of irony in the Tallahassee, FL native winning the first “golden mask” trophy on Fox’s new hit reality TV competition “The Masked Singer,” beating out eleven other elaborately costumed competitors including the other finalists, Bee (yes, it was Gladys Knight) and Peacock (Donny Osmond).

Gladys Knight’s Bee came in third place (shown here with host Nick Cannon).

T-Pain, born Faheem Rasheed Najm, is 33 now.  The Grammy-winning, married father of three used to win all the time – especially on the charts between 2005 and 2010 when he racked up more than a dozen top-10 hits on the Billboard Hot 100, including three No. 1 singles.

His hit-making days have since been fewer and farther between, though, with his last Hot 100 entry coming in 2013.  He released an album Oblivion in 2017, but it got no higher than No. 155 on the chart.  It came during a period of depression for the singer who says he began to let all the criticism of his music get to him.

“I was depressed and I wanted everybody else to be depressed,” he was quoted as saying in a recent USA Today article about his post-hit-making period.  He says he once felt self-pity in the wake of all the social-media taunts he received, including some who went as far as to suggest he should kill himself, presumably for unleashing his brand of Auto-Tuned singing to the world.

He now says he shed the depression when he learned to ignore all that noise.  Now the only noise that matters is the musical growl of his one-eyed, gap-toothed, fuzzy blue Monster that’s reintroduced T-Pain to the spotlight.  

In a weird way, “The Masked Singer” is the perfect show for giving someone like Pain a second chance.  It’s an opportunity for someone who’s been discarded by society because of who he is to display his talents on a national stage without the prejudices that would have come with knowing his true identity.

The same could be said of all three finalists really.  All are former Billboard pop chart toppers from long-ago eras (Gladys Knight hit No. 1 in 1973 with “Midnight Train To Georgia” and in 1986 as part of Dionne & Friends on “That’s What Friends Are For,” while Donny Osmond topped the Hot 100 with “Go Away Little Girl” and his Osmond Brothers’ hit, “One Bad Apple,” both in 1971).

Donny Osmond’s Peacock

Neither Knight nor Osmond has even sniffed the top of the charts in three decades, yet their masked characters Bee and Peacock finished third and second place, respectively, on the popular TV show.

But it’s T-Pain who hopes to parlay his “Masked Singer” win into a career comeback as the 2010s come to a close.  And he could take a few pointers from his fellow finalists in doing so.  Gladys Knight scored a comeback in the late 1980s with her soul chart-topper “Love Overboard,” her first top-40 pop hit in over a decade.  Osmond returned two years later with the No. 2 hit “Soldier Of Love,” the first time he’d reached the Top 40 in ten years.

T-Pain surprise-released a new follow-up album called 1UP on Wednesday to coincide with a surprise of his own: a career jolt he never expected to receive.  “I got into ‘Masked Singer’ just to wear the costume,” he says.  “I didn’t expect to get past the first episode.”

On Wednesday he was unmasked as the show’s first winner, doffing the Monster mask that for weeks concealed his true identity – an identity he wasn’t too happy about just a couple years ago.  For nine episodes, he showed people a side they were mostly unfamiliar with as he sang – yes, in costume – but with his natural, un-enhanced singing voice being front and center.

The newly crowned T-Pain (Monster) and host of “The Masked Singer,” Nick Cannon.

He says he appreciated being “treated with respect” and that Monster allowed him to perform “without the fear of being judged.”

Except, ironically, he was being judged.  

And this time, once again, all he did was win.

Congratulations, T-Pain. 


DJRob is a freelance blogger who covers R&B, hip-hop, pop and rock genres and lots of music news and current stuff. You can follow him on Twitter @djrobblog.

By DJ Rob

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