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Spoiler alert: This story contains information about contestants eliminated on Wednesday’s (March 1) episode of The Masked Singer.

The Masked Singer celebrated New York Night on Wednesday with a stellar lineup of performers who paid tribute to the Big Apple, including one who helped spark one of the city’s most iconic contributions to music history.

Looking to punch her ticket to the quarterfinals, two-time champ Medusa thrilled the crowd with a sensual take on Frank Sinatra’s “New York, New York,” kicking off the evening’s entertainment accompanied by a virtual string section.

Next up was Polar Bear, who entered to the strains of Vanilla Ice’s “Ice Ice Baby,” as his helpers sprinkled him with fake snow. With a costume featuring a handful of gold chains, tinted shades, a bedazzled red baseball cap tipped to the side and an outfit covered in vinyl LPs, PB was indeed too cool for a season 9 that has already seen the unmasking of actor/comedians Dick Van Dyke (Gnome), Howie Mandel (Rock Lobster) and singers Sara Evans (Mustang) and Debbie Gibson (Night Owl).

The clue package provided plenty of obvious details, including that he was from New York, a reference to the city getting a “bad rap,” scratching (and turntables), a childhood obsession with taking apart and re-assembling electronics, and a “message in a bottle.” What followed was a rocky run through Blondie’s legendary 1980 rock/hip-hop crossover “Rapture.”

And while PB’s falsetto was no match for Medusa, he did his best to croon (most) of the song’s lyrics as dancers dressed in taxi costumes crisscrossed the stage behind him and a Statue of Liberty popped and locked her way out of the subway. Strangely, he never got around to Debbie Harry’s rap in the tune, which was significant when you found out which Rock and Roll Hall of Famer was under the fur.

The guesses were mostly close, but no cigar, with Robin Thicke guessing DJ Jazzy Jeff (who is from Philly, FYI), always-wrong Ken Jeong guessing Diddy (right city, no RRHOF), and Jenny McCarthy-Wahlberg guessing Public Enemy’s Flavor Flav (right city again and in the Rock and Roll Hall of Fame, but also wrong). So it was up to Nicole Scherzinger to correctly guess that the fly bear was none other than hip-hop originator Grandmaster Flash.

The night also featured the five-headed California Roll taking on Lady Gaga’s “Paparazzi” and Billy Joel’s “Uptown Girl,” while snagging the group’s champion crown and punching a ticket to the quarterfinals, while Medusa was saved by the “Ding Dong Keep It On” bell.

Billboard spoke to Flash before his elimination, during which the rap legend talked about singing in public for the first time, his kids clowning him for playing dress-up and why Singer was the perfect way for the 65-year-old to keep tapping into his childlike wonder.

Had you ever seen this show before they called you?

No. If I’m not traveling somewhere or touring or lecturing or doing something adult, I’m sleeping because I’m tired. My schedule is pretty rigorous. I can remember friends and family members talking about this show, so I went online and looked at some episodes and a week or two later the call came into my office and I paused and asked, “Why would they ask me, the icon that I am?” I release my stress by grabbing some crayons or paint and getting on the floor [with my kids] and that’s very healing. This Masked Singer show should teach some of our adults that it’s okay sometimes to be a kid and be wiling to look the silliest you ever had. I’m the coolest of the cool in my world of hip-hop, so I had to come off my cool and be childlike. 

Why’d you pick Polar Bear?

I’m looking at the Polar Bear with no extra stuff and my adult is kicking in in full: it’s not cool enough. Then they came back with the chains, then the hat backwards, then the shades and sneakers and then at the moment I shut off my adult.

It’s hip-hop’s 50th anniversary and you sang “Rapture,” the song that probably clued most non-rap fans into the genre. Was that your call?

I was asked to pick some songs and I picked a few and that one felt right enough because there is no way I’m going to do a rap song, they’d have chose me right away. It needed to be that on-the-fence song, with enough singing but some representations of hip-hop. I would say it was the perfect song for this venture. I wasn’t going to rap because that would give the damn thing away.

I’m not knocking your skills at all, but it sounded like you struggled with the singing bit? Safe to say that this is your first time singing like that onstage?

Oh my goodness. before I left for L.A. they asked me to sing into my phone and send it to them and two days later they were like, “you’re kind of out of key.” I don’t sing anyway, so they said they would set me up with vocal coaches in L.A. When the hour came I had to do this song over and over and over. I was getting slightly annoyed, but I said I will stay childlike because I’m doing this for a reason. I got as close as I could get with it.

You’ve been a performer for 50 years, but did this make you nervous?

This was the most nervous performance I ever did. I’m wearing these super oversized shoes, oversized gloves and this tent [-like costume] and Medusa is saying to me, “act cool and have fun with it” and I’m sweating bullets and I’m nervous. But the the cue came and I see the screaming people in the pit and it brought me back to my childlike self and I said, “Flash, you gotta pull this off!” So, I hit my poses and sang the song.

Be honest: Is this the weirdest gig you’ve ever had?

Oh yeah by far this is number one. By far the weirdest Thing I’ve ever done. But from a heartfelt point of view, try being a kid sometimes. It’s healing. You forget about the problems of the world, your mortgage, your car, and just be a kid. That kept me in the moment.

Did any of your kids give you a hard time for doing this?

I got lots of phone calls, mostly saying, “Why did you do that?” And when I told them the phone got quiet. But the kids were getting at me: “You look stupid.” “What was that song you was singing and why was you doing that?” Definitely some mixed emotions from my children.

This year we’re celebrating hip-hop’s 50th anniversary, what else can we expect from you now that you’ve checked Masked Singer off the list?

Being one of inventors of the culture, I’m doing major lectures for huge companies, I have a big tour coming, I stream every Thursday on Twitch, I have merchandise on the way on my website, and I’m talking more about the history [of hip-hop] because I’m one of the inventors. I never imagined this [Masked Singer] for me either, but I did it and I loved it.