I've been following this guy on Instagram. He's pretty funny, smart, and gives a Trumpers a lot of crap.

There has been lots of studies on this, and part of the issue is how do you get an honest rating of someone's happiness?
Here is an (10 year old) article from Time about and how studies show it's not an easy thing to judge.
Summary:
Self-Reported Happiness: Conservatives often report higher levels of happiness compared to liberals.
Research Studies: New studies indicate that conservatives may judge their lives and circumstances more positively than liberals.
Emotional Language: Analysis of transcripts from Congress shows that liberals use more positive words than conservatives.
Genuine Happiness: Studies on smiling intensity suggest liberals display more genuine happiness.
Impact on Behavior: Conservatives have a more confident style of self-assessment, which might contribute to their reported happiness.
The research suggests that the way conservatives and liberals perceive and report their happiness might be influenced by their self-assessment styles.

Stupid people tend to be happier, yes it's true.

Are they happier? Because they sure do complain a lot and get enraged over the simplest of issues.

Love Steve. Been following him for years.

"Fuck you, got mine " exemplified .

If conservatives were happy they wouldn't act the way they do.
- I have a conservative friend who will start screaming like a little girl when a cyclist is doing nothing other than just using the bikelane that happens to come into an intersection with the road he's on.
  Such happy people, amazing.
  
  Tell him we hate him too
  
  Why are you friends with douchebags? I'm not trying to be snarky, I am genuinely interested

More like blissfully ignorant. My experience with conservatives is that they like to sweep problems under the rug and pretend everything to be fine.
- I realized it's very much this when I asked my mother (born in 1961) if she had never taken a civics class, and she answered no. She actually believed(s?) the president creates laws. I don't know what she thought congress was.

ahh yes family values like bailing Andrew Tate out.
- Not to mention worshipping a thrice-married sexual predator
- Andrew Tate and his brother have probably, uh, you know...

Privilege. Especially white privilege. It's easier to be happy when you're benefiting from the invisible suffering of others.

Ignorance is bliss, and to persist with conservatism requires embracing an ever expanding level of wilful ignorance.

He does stand up. He's pretty funny. I like when he heckles back at hecklers.
- The funny part is that he’s known as a heckle comedian but has publicly stated that he hates hecklers. He’s only known as a heckle comedian because he has zero qualms about tearing them down as soon as they try. His comebacks are usually pretty brutal because he just wants to end the heckling and keep his set moving.

Stop censoring these people's names and faces. They said it. They said it out loud and proud, in front of god and everyone. Why are we afraid to show them?!
- Some places do have rules against name and shame, to be fair. Not sure that this is one of them, but still a safe general rule to follow.
  
  Those places deserve pushback on that bullshit
  If someone said it in public then they're fine with it being out there
  
  You may be looking for the phrase "chilling effect". It's not just for legal stuff now, but for doing anything proper because it brings too much trouble.

Conservatives are racist nazis that have the IQ of an inbred redneck
- I'm a redneck. Not inbred more than normal, as far as I know. I think I'm purty smart sometimes. Since you and I are 50th cousins, at worst, you've got some redneck in you.
  Don't be like the fascists. Don't get lazy in your thinking. Our antagonists are human, some are very intelligent.
  To defeat their ideology, we must view them accurately. Otherwise, how will we anticipate what they will do?

I've noticed that conservatives cant feel empathy. They only feel sympathy. This is why they don't understand any injustice until if effects them personally. This is the root psychological reasoning behind the leopards eating faces memes.
- The richest man in the world, who has only ONCE paid anything approaching a 20% tax rate and crowed like he was a PHILANTHROPIST when he did, is removing all social programs that are a safety net for the poorest and most desperate among us.
  Empathy? Sympathy? They are vampires.
  
  I prefer to call them Ghouls.

Well, they do say ignorance is bliss.
- They must be euphoric.
- Oh boy, you have no idea how much. Imagine knowing you will be tortured for eternity.

"We're happier than libruls"
Must be the whole "Ignorance is bliss" as well
- I'm pretty sure that they are "happier" is not a factual statement.
  
  Was going to say, most that I know seem pretty miserable and looking for someone to blame or hate
- Like a cop beating up a suspect they're... happy.

Lack of empathy and utterly selfish. It enables these trash humans to take others rights and believe the lie that doing it is a good thing.

Yeah I was going to say to stupid to know any better.

People these days seem happiest when ostracizing, excluding, and destroying another's life just because they are different.
Empathy is dead, because if you show empathy it's grounds for expulsion. Anyone still capable of empathy has been ejected from society by the twitter mob over the past decade. The only people left are callous bullies.

He's so funny, he does it for work! He's an excellent comedian, one who doesn't invite hecklers but will destroy them.
He's smart because he's educated. He's also a sharp wit but he just generally knows a lot of shit.
Sadly, his tour stop near me is too far away so I can't go.
- He's obnoxious. He's not funny. And he spams his content on multiple platforms with multiple accounts.
  
  To quote another post of yours "no one gives a shit about your preferences"
- Those hecklers are plants. How do you not know this?
  
  Source?

I've never read Flowers for Algernon.
- I don't understand why you said that, but you should. The short story is very quick.

I wouldn’t praise Hofstetter too much. His comedy is horrendous and he relies pretty much entirely on bringing in paid hecklers. Every time he shows up on PKA, he is not just unfunny but he kills all the enjoyment of the episode.
- Sorry to go to Reddit here, but here's Hofstetter on Hofstetter:
  https://www.reddit.com/r/Standup/comments/5ab3ue/do_all_comedians_get_heckled_as_much_as_steve/
  
  No shame in ~8 year old Reddit threads. It’s where all the organic content is!
- The "paid hecklers" accusation again.
  Ahem are YOU being paid? It seems a lot of people just don't like him.

Isn’t he that guy that plants hecklers in his audience that serve him meatballs so he can come off as clever and quick-witted?
- Do you have evidence that they're plants? This is the first I've heard of that accusation. He does get an unusually high number of hecklers, and it fuels a lot of his online content, so I wouldn't be shocked if they're plants, but I haven't heard any definitive proof. I'd just as soon believe that people heckle him more because they think they're smarter than his previous hecklers or want attention or something, but idk.
  
  Yeah. The dude has a TON of heckler videos. For starters.. It’s incredibly unrealistic for a comedian to be heckled that often. Secondly, his responses are always perfectly timed and executed without hesitation. Every time. With not even a slight pause or moment to collect his thoughts before tearing into the person.
  Only Robin Williams is that skilled at improv.
  I’ll add that he’s well known for behind a huge asshole in the comedy circuit. Look it up. And lastly, heckling generally gets you tossed out of clubs. None of his plants ever get tossed that I’ve seen.