If Squidward had to work in the Park from Regular Show, how he and Benson get along?

How would Spongebob and the Regular Show cast interact? I can see him hitting it off with Pops.
Squidward would probably beg Benson to give him jobs that don't involve working with Mordo/Rigs specifically and go out of his way to avoid them whenever possible.
Benson does force mandatory team outings however, so that could be a problem.

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>search "squidward benson"
>get this

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Squidward is basically a neurotic verson of Pops. Both like classical music and gardening, and Pops is always eager to cheer anyone up no matter what their interests are, so they have a chance of getting along. What Squidward might not get about Pops is how he uses lollipops as currency, so that's a recipe for being isolated from many locations or being arrested due to association.

At least it wasn't ship art

Slacker vs workaholic conflict aside, do they even have any common interests?

Well he's a Slacker but take into account that his current boss is a greedy asshole that literally had children trapped for years on his basement because their parents "forgot" about them and hates his coworker.

Being treated like a actual living being and having a good pay with benefits should make wonders for his Slacker attitude.

Music is something they have in common

>First hour of his first day on the job, he's over the moon from the lack of Spongebob in his life and gleefully hides away in a bush to sleep his way through work
>Second hour, he's flipping his shit at Mordecai, Rigby, and Muscleman for how loud they are at and disturbing his nap, only to end up in a shouting match with Benson that ends with the threat of being fired day one
>Third hour, he's on his hands and knees begging Pops to be reassigned somewhere else in the park as far away from Mordecai and Rigby as physically possible
>Fourth hour, he's confidentially standing behind the snack counter, smugly laughing to himself...until the reality hits him that he's effectively just traded one job working the register for another, and then suffers a nervous breakdown so hard that he goes on a rampage through the park, requiring everyone to team up to stop the pissed off octopus in a shirt.
>Evening time, he's being shipped back home stuffed into a pickle jar, laughing at how he's finally rid of those loud, annoying jerks and can get some peace and quiet.
>Midnight, he's woken up by Spongebob's laughter due to the party he's throwing for his new pals Mordecai and Rigby, and the screaming never stops

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>assuming Squidward and Benson are in the same position
They'd get along great and probably bond over yelling at Mordecai and Rigby
>assuming Squidward has Benson as his manager
They fucking hate eachother. The screaming matches can be heard a county over.

>Being treated like a actual living being and having a good pay with benefits should make wonders for his Slacker attitude.
Depends on where it comes from. There's a pretty solid argument to be made that Squidward would slack off at any job that he thought was beneath him, which considering his ego would be anything short of being a professional musician or artist. The only time we really see him dedicated to a "job" is band geeks, as far as I can remember.

Am I crazy to think that Benson would actually be a pretty easy going boss?

This is eerily reminiscent of the dialogue from one of those shitty early 2000’s cartoon network flash games