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Music Monday: The Word of the Day is ‘Hat’ – Power Ranking Sesame Street’s Singing With the Stars

With the X Factor NZ going from bad to worse, Alex Casey watches Sesame Street’s Singing With the Stars in an attempt to get back to the music. 

Sesame Street first began in 1969, and in its first season featured the cameo appearances of BB King, Don McLean and Carol Burnett. Over the next few decades, the list of celebrity guests absolutely snowballed out of control, careering down the slopes of musical fame until it hit the likes of LL Cool J square in the face. I found the ultimate collection in Singing With the Stars, a 50 minute journey through the best and worst acts that have ever bobbed down Sesame Street (sans a hand up their butt).

Here are the stand-out performances, evidently ranked mostly by hat strength:

1) Jason Mraz, ‘Outdoors’

Song: This agoraphobic anthem combines Jason Mraz’s classic ‘I’m Yours’ with the crushing anxiety of a person completely crippled by their fear of the outdoors. The opening lyrics “all day I’ve been inside and I’ve got the feeling – I’m trapped between the doors and underneath the ceiling,” would be enough to send someone into a panic room for at least a week.

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Hat: At first I thought it was just his simple black number that we all know and love. As he tipped his head forward, more and more coloured stripes were revealed. Like some sort of never ending PH test for dork-levels.

2) Destiny’s Child, ‘A New Way to Walk’

Song: Having a new walk is fine and all, but I get a little grossed out seeing Elmo in a long shot. He doesn’t move half as naturally, and looks exactly like the precursor to the bone-chilling Futterwacken of Alice in Wonderland fame. I would like to think that this track gave D.Child strength for this powerful stomp to come in later years

Hat: There was a bountiful time on this Earth where every $2 shop stocked Beyoncé’s red pleather baker boy hat. But this one has a slight beret feel to it, perhaps military. Alright Bey, didn’t realise you were in the 82nd Airborne Division of the United States Army.

3) Goo Goo Dolls, ‘Slide (Pride)’

Song: The Dolls asked Elmo what he had done that day that made him feel proud. All that red sloth had managed to do was reach a shelf, drink some milk and help his Mum bake a pie. Don’t get too high and mighty there mate. Also, who knew Elmo had a Mum? Here she is reading this critique and agreeing that her son could definitely achieve much more in a day.

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Hat: Ain’t nothing like a flexifit cap and some urine-tinted glasses to remind you of the good times. It’s not quite a hat, but also worth pointing out that lead singer has the exact same hair as Theresa Caputo of Long Island Medium fame.

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4) *NSYNC, ‘Believe in Yourself’

Song: “You can be what you want to be,” Lance Bass sang to himself, long before he had his dreams of travelling into space ripped right out from under him. I can’t take this song seriously, knowing that only a few years later JC Chasez would rip through the charts (farts) with this truly atrocious number. Maybe sometimes you shouldn’t believe in yourself, or do what you want to do.

Hat: JT’s frayed cargo bucket hat screams casual teen. In fact, my partner at social netball last night was almost wearing the exact same one. Basically the definition of a relaxed youth on the brink of huge musical stardom and/or social sporting success. Nicely offsets the exuberant twinkling earring that lies beneath.

5) LL Cool J, ‘The Addition Expedition’

Song: Sir Cool James has not spent this much time with chatty birds since his career-defining role in Deep Blue Sea. The song itself is quite handy I suppose, but it’s not so much about adding as just basic counting. LL seems to look slightly past the camera, which really makes it look like he has a gun to his head.

Hat: Classic black backwards cap, a hell of a lot slicker than that absolutely gaga Goo Goo number that’s for sure. A shame he didn’t collab with Beyoncés stylist and come through with this.

6) Hootie and the Blowfish, ‘Hold My Hand’

Song: I mean yeah, crossing the street is hard and scary. But I don’t know if encouraging kids to hold the hands of strangers willy nilly is the best idea. This problem could be avoided if all kids just took a leaf out of Jason Mraz’s book and stayed behind the firmly locked doors of a local laundromat at all times. Topic aside, I loved how much the Sweater Blowfish hated this gig:

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Hat: I would rather get bit by a tram than hold the hand of that damn Cheesecutter Blowfish.

7) James Blunt, ‘My Triangle’

Song: “This shape was brilliant, this shape was pure. I saw three angles, of that I’m sure.” Booya. Triangle. Got it on the first go and everything. Didn’t even have to Google it. What I could not have predicted however, was just how deep Blunt’s perverted triangle lust went. “My dreams are triangular every night.” Sick! Then he finally found the triangle and hugged it near to his groin. Never let the Blunt on the Street again.

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Hat: There was no visible hat, just this spiritual hat.

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Lightbox users, click here to see the finest musicians and headwear that Sesame Street has to offer. It’s fine for kids, and 23-year-olds alike. 

Everyone else, make like LL Cool J – click here to go on addition expedition and become a part of the Lightbox equation.