Believe it or not, when Nick had first started chatting online with ‘SHERIFFNORTHSTR’, he had seemed almost normal. Well… as normal as someone that active on a Cowboy Roleplay forum could be.

The first thing he had learnt was that the guy apparently went by ‘Sheriff North Star’ – his username merely shortened to fit the fifteen-character limit. The second thing he had learnt was that the man never broke character – Nick had tried asking the guy where he was actually from on multiple occasions, but North Star had waxed some weirdly poetic stuff about coming from the ‘Wild East’, which he governed with an iron fist, bringing order to an unruly town…

It was, to be frank, slightly cringe-inducing but… the guy was super genuine. Even if he maybe was a little too into this cowboy business. Given the chaos and turbulence of the world lately though, Nick found it hard to blame him. The stress of it all had led to him trying to recapture his childhood, hence his scrolling through these old, dated web forums… this ‘North Star’ was likely in the same boat.

So, despite the other man’s oddities, Nick had kept chatting to the guy. Message after message, by this point, North Star had insisted Nick just called him ‘Starlo’ – obviously another fake name – and Nick had become Starlo’s loyal deputy, the two holding conversations over text everyday now and sharing stuff with each other… and then Nick, not even realising the can of worms he was opening, had asked it:

WRNGLERNICHOLAS: so what do you think of all this monster stuff?
SHERIFFNORTHSTR: Hm? Whaddya mean, pardner?
WRNGLERNICHOLAS: do you have to ask? the fact that there’s been actual MONSTERS living underground all this time?
SHERIFFNORTHSTR: Oh

There had been a solid five minutes of inactivity… and given this was Starlo, who would type away without response for HOURS if you got him on a tangent, that was of concern. Nick had been beginning to suspect maybe it was a sensitive subject somehow when—

SHERIFFNORTHSTR: Are you scared of Monsters?
WRNGLERNICHOLAS: huh? well… I mean I’m not the biggest fan of the political shitstorm going around the world cause of it. some people say we’re going to war again, that’s pretty scary
SHERIFFNORTHSTR: But what about the Monsters themselves?

That had Nick pausing. Obviously, he had stared at the grainy pictures just like everyone else online – it had been hard to make out much though. He hadn’t really thought much about the Monsters themselves though – outside of the possible danger and chaos they posed.

WRNGLERNICHOLAS: idk – I guess I haven’t really considered that. word online is that the monsters are pretty pissed at us – so that’s probably bad news
SHERIFFNORTHSTR: Well Humans did lock Monsterkind underground for centuries – I think the anger is slightly justified.
WRNGLERNICHOLAS: where did u hear that from??
SHERIFFNORTHSTR: Around

Another pause, as Nick blinked, quickly typing it into google to see if anything popped up but…

SHERIFFNORTHSTR: It’s okay though. I think Monsters are willing to move past all that. Lots of them want to move up to the surface and see Humans and their culture for ourselves!!
WRNGLERNICHOLAS: how do you know all this???

This time ten minutes had passed. It was obvious that something was making North Star anxious.

WRNGLERNICHOLAS: is everything okay, starlo?
SHERIFFNORTHSTR: Do you trust me, Deputy Nick?
WRNGLERNICHOLAS: of course – even if that’s probably dumb, lol

Nick had been prepared for a variety of confessions here, his money had been on Starlo deciding to come out right then and there for some reason (as if he hadn’t been so blatantly obvious about it up until now…) but instead—

SHERIFFNORTHSTR: I’m a Monster
WRNGLERNICHOLAS: ur a monster? like… a metaphorical one or
SHERIFFNORTHSTR: No. A Monster – the ones you’ve been reading about in the news.
WRNGLERNICHOLAS: holy crap… you’re being serious.

Starlo would tell him later that the following five minutes had been some of the longest five minutes of his life, right up until—

WRNGLERNICHOLAS: well… crap – guess i’ll actually be able to see you soon, lol

In hindsight, it had been obvious. As it turned out, all of the weird man’s oddities and quirks had a very reasonable explanation behind them… and of course, Sheriff North Star’s name actually was Starlo. A few weeks after that conversation and they had exchanged pictures… with Nick groaning at the annoyingly adorable, weird… star-thing on the other end of his screen.

On the plus side though, Nick was scrolling through the news with a lot less nervousness than before. If Starlo was one of these monsters, surely they couldn’t be that bad? They had made plans, Starlo was on board to be in the first ‘group’ of monsters allowed to traverse to the surface. Nick had travelled across state lines, even booked a hotel nearby and had been nervously waiting in a field, peering at the horizon to spot his Monster friend approaching when—

thoom… Thoom… Thoom… Thoom… THOOM!

His mouth had dropped open at the… the fucking GIANT approaching. He would have been screaming and running for his life if he didn’t recognise the goofy attire and beaming face of—

“Deputy Nicholas! That you? Kinda uh… hard to see ya!”

Nick’s eyes bulging, had immediately started a call with the towering monster.

“W-why the hell are you so BIG, Starlo!?”

“More like why are y’all so small… ya never told me that, Nick~”

“I… h-how did this not come out before…?”

“Dunno pardner, let me tell ya, it was a mighty shock when we all arrived on the Surface. I uh… nearly stepped on some poor varmint! Hahah… his face was pale – white as a bone!”

Sheriff North Star – the utter dork he had come to know as Starlo – stood just below a causal 300ft tall. Or, from Starlo’s perspective – Nick came barely above two inches tall. To say it had Nicholas feeling slightly rattled was putting it nicely – his gigantic sheriff at least seemed to find the whole thing amusing.

“Darn… we were going to have a dual! I think the ten paces back affair might make that a bit awkward though…”

“Duel – not dual.” Nick corrected for the hundredth time. “A-and I think we have more pressing matters than that, Starlo!”

“Huh? What’s up, pardner?”

“I… I was supposed to take you on a trip to see all those western landmarks you wanted to see so bad, right?”

“Yep!”

“You… you might be just a bit too big for those, Starlo…”

Nick had paused at the blinking above and the sudden downwards tilt of the mouth.

“Aww… really? You absolutely sure? I’ll be careful!”

“Well um…” Nicholas cringed, flexing his fingers… bringing his towering friend anywhere was going to pose a problem… not to mention the obvious logistical and personal dangers of being around someone so big… but that damned, disappointed face looming above…

“I guess… rides and stuff are off the list but… some of the landmarks we can still visit?”

The following grin of excitement was enough to shove away some of Nick’s bigger doubts, but…

“I was planning on hiring a car, but…”

“Nonsense! All your cities are so small – I’ll walk us there!”

“STARLO-“ The tiny man had only gotten the chance to squeak before the massive sheriff had abruptly picked him up, kidnapping him in his warm leather glove before depositing him on a shoulder. A panting Nick clung for dear life, staring up at his titanic friend… who turned his head to stare at him with a grin.

“You can say giddy-up if ya want, Deputy Nick~”

…goddamn it. This nerd was going to be the death of him… but Nick cleared his throat and said it anyway, a gasp leaving him as he grabbed onto the poncho for dear life.

“So where we heading first, pardner?”

“T-there’s a bit of a cowboy meetup an hour or so to the south! They’re gathering around one of the landmarks I wanted to show you… the er… World’s Largest Cowboy Boots…”

“World’s Largest Cowboy Boots!? Now that sounds like my kinda thing, deputy!”

Giving a nervous chuckle, Nick nodded and carefully leant himself against the warm yellow neck to his side. Glancing down, the human sucked in a breath at just how high up he was… come to think of it, this landmark wouldn’t be nearly as impressive considering Starlo’s… size. In fact, he’d no doubt outsize it by a significant margin… said thought had a strange fluttering feeling start in his body.

Oh… oh dear.

He was in for it now, wasn’t he?

===

A commission done by the wonderful  a2malgam that me and  JordilianVector grabbed after finishing Undertale Yellow at the end of last year. Happy one year anniversary to Undertale Yellow - you can download and play it for free right here!

So, for context, last year I saw some fanart of this blessed cowboy himself, immediately I was intrigued. Looking him up I realised he was from an Undertale fangame that had been released a week back… I of course immediately enlisted my resident Undertale fan friend JV into playing it for me – and we absolutely loved it! As you might imagine, us being us, we knew we had to grab art of this towering dork, and so we got our friend A2 to play Undertale Yellow and proceeded to shamelessly ask him after he finished if we could commission him for macro Starlo – here’s the results of it.

I had a very strong image in my head of Starlo measuring up his own boots next to the ‘World’s Largest Cowboy Boot’ – and JordilianVector edited in the dialogue box and sprite for me. The story there was something I came up with… and I’m not against exploring it in more depth one day, I am exceedingly fond of this silly star-corn sheriff man…