All aboard the Pineapple Express: 'The Masked Singer' is a ride straight to Crazytown

This show is weird, you guys. In the best possible way.

For those of you not already flummoxed and/or fascinated by last week’s totally bonkers The Masked Singer Fox premiere, when NFL troublemaker Antonio Brown performed Bobby Brown’s “My Prerogative” in a hip-hop hippo costume — or by Ryan Reynolds’s unicorn-headed viral performance of the Annie ballad “Tomorrow” on the original Korean version of this game show — allow me to explain, once again, The Masked Singer’s bizarre AF premise:

A dozen cosplaying mystery celebs, their faces shielded by giant masks that make Slipknot look like amateurs who shop at the Halloween superstore, sing karaoke for fallen pop star/Duets judge Robin Thicke, Community comedy doctor Ken Jeong, former Singled Out sidekick Jenny McCarthy and onetime Pussycat Doll/Popstars contestant/X Factor judge Nicole Scherzinger (and exiled America’s Got Talent host Nick Cannon, of course).

This esteemed judging panel watches an hour of what basically looks like Eurotrash band Alacazar’s infamous “Crying at the Discoteque” music video and then makes terribly uninformed and almost always incorrect guesstimates about these masked men’s and women’s true identities. (Thicke hasn’t been so wrong since he thought recording Paula, an entire album for his estranged and put-upon first wife, was a good idea.) At the end of each episode, one contestant is unmasked — and the internet predictably breaks. The show is already a breakout hit after one episode.

This week’s second unmasking victim was the one flora-not-fauna character of the entire competition, the Pineapple — who turned out to be Tommy Chong (of Cheech & Chong fame) semi-singing “I Will Survive.” To McCarthy’s credit, she guessed correctly for once — but she also guessed Cheech Marin, so she doesn’t win too many bragging points. I guessed correctly too, since this one was pretty easy: The Pineapple’s clues package was full of stoner references, and he’d mentioned that he’d beaten a “life-threatening disease.” (Chong has battled cancer twice.) Chong was eliminated this week, so he took the Pineapple Express straight off the show, his chances of winning up in smoke.

Watching Chong’s bananas Pineapple performance, frankly, made me feel like I was stoned. Like I said, this show is weird.

Anyway, last week’s episode had everyone in America trying to guess the famous faces behind the façades of the Peacock, Monster, Unicorn, Deer and Lion, all of whom will be back to rock the mic and boggle our brains next week. Below, let’s look at this Wednesday’s five other, non-Pineapple mystery singers — the Raven, Alien, Bee, Poodle and Rabbit — and play the guessing game that has become the new national pastime.


Clues: This rascally rabbit, who hopped onstage in a straitjacket and twitched creepily through a very loca performance of “Livin’ La Vida Loca,” said he’d spent “most of his life onstage, but never alone.” He revealed that “synchronized singing is his forte” and he’s been in a band before, and said now he “pops up all over.” This all led the judges to speculate that the Rabbit might be a former boy-band pop star.

Judges’ guesses: Lance Bass, Justin Timberlake, Joey Fatone, Jake Gyllenhaal (because of the performance’s “Donnie Darko vibe”) or weirdo escape artist Criss Angel.

My guess: Donnie Wahlberg. His Wahlburger fast-food chain has “popped up” all over the U.S.; he’s got just the right stuff (i.e., a twisted sense of humor) to hang tough on this show; and if Donnie could fool his own wife, Jenny McCarthy, all season, that would be the ultimate plot twist.


Clues: Statuesque and sexy (“the hottest alien I’ve ever seen,” raved a practically salivating Jeong), this contestant revealed that she has “many sisters” and that in her family, “anonymity is a completely alien concept. Growing up in the public eye, my life was never really my own.” Her merely decent voice on Portugal. The Man’s “Feel It Still” indicated that she’s not a professional singer, but her lean frame and red-carpet-ready, hand-on-hip pose had the judges thinking she might be a professional fashion model.

Judges’ guesses: Britney Spears (because of the Alien’s slick red latex unitard), Bella Hadid, Kourtney Kardashian or one of the Spice Girls.

My guess: Kendall Jenner. The judges were onto something with Kourtney, but they picked the wrong Kris Jenner spawn, methinks. Besides having the applicable lanky body shape and model pedigree, Jenner once rocked a temporary snake tattoo for V magazine — and the Alien’s clues package featured a slithering snake. That reptile reference may have also been a jab at Jenner’s former friend Taylor Swift.


Clues: The Raven said she’s “listened to other people’s stories” all her life (she’s hosted a talk show in the past) and has “always been a sunny kind of person.” She also “recently suffered a tragic loss,” so her surprisingly sweet and elegant performance of Kesha’s “Rainbow” was a “chance to honor her beloved.”

Judges’ guesses: Sherri Shepherd, Sally Jessy Raphael or Star Jones.

My guess: Kathie Lee Gifford. Besides the fact that she’s a chat show veteran with a bright disposition, her beloved husband, Frank, died in 2015 — a “tragic loss” for sure. Kathie has also been known to break into tears on the air, so the Raven’s “don’t cry, baby” line may been a sly, self-deprecating remark.


Clues: The Poodle said she has “loved to be onstage taking on different characters” since she was a little girl, and she’s from a musical family but is known for a “different talent.” (Her throaty performance of Pat Benatar’s “Heartbreaker” was actually solid, though.) Rainbow imagery and mentions of “free speech” in the Poodle’s clues package indicated that she’s a member or ally of the LGBT community, and there were multiple references to standup comedy and San Francisco as well.

Judges’ guesses: RuPaul (bad guess, since this contestant is only 5 feet 5), Richard Simmons, Ruth Bader Ginsburg (because the Poodle said, “I am here for your honor”) or Ali Wong. Clearly these judges have no idea what they are doing.

My guesses: This one is admittedly tough, but I am going to go with Nicole Richie. She was born in the Bay Area; she’s the adopted daughter of Lionel Richie and niece of Sheila E.; she’s funny and mouthy; and that fabulous, best-in-show pink Poodle outfit was certainly worthy of a fashion “it” girl like Nicole. She also has a well-known fondness for small, fluffy dogs. (Runner-up guess: It’s a long shot, but it could be Mackenzie Phillips. I may be wrong, but it’s more likely to be a ’70s sitcom actress than an actual Supreme Court justice, right?)


Clues: A clearly seasoned R&B diva who handled Sia’s “Chandelier” with ease and grace, the Bee said, “You can call me Queen Bee, but Empress also suits me.”

Judges’ guesses: Beyoncé, Cardi B, Diana Ross, Mary J. Blige, Lil’ Kim, or some Empire cast member — but that was before the Bee confessed that she’s been performing since the 1950s. At that point, Scherzinger switched her guess to Dionne Warwick.

My guess: Gladys Knight. I feel very confident about this one. Besides this performance sounding like Knight, and Knight first gaining fame as a 7-year-old talent show winner in 1952, Knight is commonly known as the “Empress of Soul.”

Keep tuning in each week, to find out who will be the last mask standing.

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