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The Best & Worst Wingmen On Sesame Street

The Best & Worst Wingmen On Sesame Street

Being single around Halloween has it's benefits. For instance, you don't have to worry about getting roped into some horrific shit like this:

That heartbreaker on the right is redefining blue balls with that Blue Steel stare.

That heartbreaker on the right is redefining blue balls with that Blue Steel stare.

But that also leaves you as a person on an island onto yourself. Sure, you could go as Gilligan or Tom Hanks with Wilson to self-depricate and bottle up that unexpected loneliness of your late 20s or you can hit the streets with the help of a wingman. Oh, what street, pre-tell, Dominic?


Whether she's dressed up as a sexy R2-D2 or she's your regular plain-clothed Jane, 123 Sesame Street is not only swarming with good vibes and the joys simple math, but furry creatures to help (or hinder) you when you're attempting to pick up that special gal. And there's quite the spectrum of which Muppet is top-notch and who may swoop in and get those digits instead. Starting from worst to best, let's show you how to get her to Sesame Street:


10. Elmo

I'm not mincing my words when I say that Elmo is your worst possible option. He may have that "hey, check out my adorable puppy that happened to cross your path" glow to him, but Elmo's dumber than a bag of bricks. Always asking questions, always not talking in complete sentences. Think how many times he'll interrupt the conversation with "Elmo loves pinball. Where's pinball?" or "Who wants to play the matching titty game on the bar computer? Elmo does!" Fuck that. He may be one of the tops at consoling and building your lonely ass up when you're down, but he'll be sure to get you there quicker. Stay the fuck away from Elmo.

Wingman Rating: 2.7


9. Ernie

I don't know, I kinda don't trust Ernie. Just reference his dynamic with Bert: Ernie's the star of the show. You better believe it'll be the same thing with a night out on the town. Gonna be all about him. Plus, he's a notorious troublemaker and button-pusher. I could easily see him cheating at pool or unknowingly talking himself into some unnecessary predicament that gets him a shot glass smashed off that orange dome of his. Very high candidate to get arrested on some sort of public misdemeanor.

Wingman Rating: 2.9

8. Telly Monster

Listen I'm all for empathizing or sympathizing with anxiety/depression issues (I fall into the sympathize category), but it's never good when you're trying to woo the rightful candidate. Telly Monster is a bundle full of emotion and with as much worrying as he does, he's a pretty solid ringer for somebody with OCD. You take him out, you run the risk at him bending your ear all night about his broken tuba at home, where he put Freddy or that there isn't enough triangles in the bar for him to feel comfortable. Get a couple drinks in him and he's on another level of panic. Plus he looks like Leslie Nielson, and we know about Lt. Frank Drebin:


Wingman Rating: 3.4


7. Count von Count

Count is one of the best Sesame Street characters, but put him in a situation where there are an insurmountable things to count and you have a huge problem on your hands. He'll be counting your drinks, her drinks, the bottles of booze behind the bar, everything. Could lead you into an unwanted scuffle with a drunken derelict that's bad at arithmetic ("tell that purple fella to shut his damn mouth") or just the sad acceptance of youth passing you as you realize you're slurring words only four beers in. That's not even bringing up his natural vampire ability of hypnotic charm so you might walk up without a shot in the first place.

Count on not getting any more numbers other than the ones Count be counting (but if you do happen to get them digits at least he'll remember them for you).

(Note: Shem The Pen thinks Count should be much higher, like top three. Says he's got swag style and a castle to boot. Fair points, but I'm telling ya, the counting is really gonna screw things up. SHEM THE PEN: "The Count is the only Sesame Street character with any real swag level for the bars.") 

Wingman Rating: 4! (4 Rating Points! Ha ha!)


6. Cookie Monster

Looking for the weekend equivalent to an Andrew W.K. song? Then take that wacky bastard, Cookie Monster with you. No doubt a surefire good time with him out and about. The guy's gonna be a hit wherever he goes: house parties, bars, tailgates - you name it; CM will burn the house down, rebuild it, and burn it down again. The Gronk of the Muppet-verse. Only downside: he probably doesn't know his limits. He's proven that with cookies, how's he going to be when he's got three shots of Jack lined up in front of him? Good times, but very rough times ahead. Lots and lots of cookie tossin'.

Wingman Rating: 5.5


5.  Big Bird

Walking into a bar or club with an 8 ft tall yellow bird may not provide the best visual, but once you get Big Bird nested into the environment, he's got the potential to shine.  Bird's a dreamer, so you know he's going into the situation with the right mindset. Some of the riff-raff there will be so infatuated with him that it opens up more opportunities for a little one-on-one conversation. The only downfall with dreamers are that they tend to get a little sidetracked (if "Follow That Bird" taught us anything it's that he can just up and leave) so you may be left to your own devices without any back-up. However, that constitutes enough wingman cache to get the Street's main guy into the top five.

Wingman Rating: 6.4


4. Bert

You could absolutely make an argument for Bert to be in the top three: he's straight-laced, really loves books and by most regards doesn't drink so he could make a great DD. Plus, this would make him an excellent buffer between any creeps and/or mouth-breathers trying to invade your space. One question is his endurance - how long could Bert take of the clown shows of drunks around him? That DD does no good if he isn't there to be one. I don't think his fuse is extremely short, but it might not last you enough to make magic happen. Bert's all about those Irish goodbyes.

Wingman Rating: 8.0

3. Oscar The Grouch

Lots of cons on the surface for Oscar - being negative and living in a trash can are two red flags, and yes, his goal as a grouch is to put everybody in a pissy mood, but there are a couple of arguments to put him in the top five. (1) I really don't think Oscar or his trash area stinks. People and Muppets alike hang around him like he's the Dos Equis guy and that wouldn't happen if you're permeating the smells of asparagus, BO, and old Ramen. 


(2) The ladies love a funny cynic. Oscar's going to look at everything through rose-colored glasses and that could provide for some good comedy throughout the evening. Hearing him lightly bitch about the barkeep being too accommodating or that the ambiance is too warm will only make you more of a positive presence.

(3) The trash can is mobile so if things go well he can boogie the hell on out of there - no questions asked. Oscar may be a grouch but he won't stand in the way of you meeting that special somebody.

Wingman Rating: 8.6


2. Mr. Snuffleupgas

If this list was compiled before 1985, Snuffy would have been at the very bottom considering he was Big Bird's invisible friend up until then (can't be talking to no invisible friends in public), but achieving "tangible being" status to every Muppet and human on Sesame Street boosts him all the way up to number two. He's the epitome of a good friend so you know he has your back. Need him to to chat up her hammered and depressed Telly-mannered companion? He's got you. Elmo won't shut his fuckin' trap? "Let's hit up that pinball machine, buddy." To his core, Snuffy is salt of the earth and he'll reflect that as your nightlife copilot. 

Wingman Rating: 9.1


1. Grover

You need a monster committed to the cause? Look no further than Grover. He's had so many jobs that he could have a "Philip Rivers' dozen" of kids (that's eight) and still float above child support payments. Let's not forget him moonlighting as a masked vigilante on top of that. The guy gets shit done. Hell, he's been friends with Kermit even longer than the frog's been tied to Miss Piggy - even kicking it with Kermie on Ed Sullivan way back when:

Sure, the clip itself is contradictory to his wingman ability, but it's over 50 years old, the mean streets of Sesame have mellowed Grover way out since then. He's a monster of many trades and he's like Cookie Monster, but without the addictive personality. You get a bit of a wild card, but one that's knows his drinking threshold. He'll get you home and if you play your cards right, with a companion.

 Wingman Rating: 9.5

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