Title: Oh...Sir!
   The Hollywood Roast
Developer: Vile Monarch
Publisher: Good Shepherd
           Entertainment
Release date: 2017-05-31
Regular price: 3,99 €
Bundled:      ☑Yes ☐No
Achievements: ☑Yes ☐No
Cards:        ☑Yes ☐No

• Oh...Sir! The Hollywood Roast
  

  8 hours playtime

  16 of 20 achievements

cards idling: 0h

Title: Oh...Sir!!
   The Insult Simulator
Developer: Vile Monarch
Publisher: Good Shepherd 
           Entertainment
Release date: 2016-10-25
Regular price: 1,99 €
Bundled:      ☑Yes ☐No
Achievements: ☑Yes ☐No
Cards:        ☑Yes ☐No

• Oh...Sir! The Insult Simulator
  

  8 hours playtime

  10 of 18 achievements

cards idling: 0h

Sorry about the lack of images and such but I was working on some when the electricity went off. I even lost what I had already written of this post. No way I'm redoing all of that.

First of all, if you want to try one before spending any money, you can play the original, called Oh...Sir! Prototype, for free; it has only (local?)multi-player though, so you either have friends or play both characters by yourself (as I did), fixed place and characters. Didn't play it much but I assume even the sentence's pieces aren't that many. Basic, but should give you an idea.

Ok then, seems you are still interested in trying one/both of them.

Let's start with The Insult Simulator:
Compared to the Prototype, this version has more characters and places you can choose from, and every of them adds some unique bit of sentence to the match.
Other than local and online multiplayer, there's a short single-player mode composed of 5 levels: levels are static but opponents are random (except for the boss in the last level).
Every character has some argument which is their Achille's heel, talking about that in your insult will increase its strength. You can also start a combo by talking about the same thing you did in your previous insult (last one only, means works for "in a row" insults.. hope it's understandable! if you've an easier way to say it, tell me and I'll edit) but it works only with nouns, don't know why it doesn't trigger for verbs/actions.
Points are given based on how funny an insult is, the devs team decide what's funny and what not, and you don't have a way to know beforehand if your insult is going to score big or not.
Do not worry as there aren't any "heavy" insults, so you should be able to safely play it with family/kids. Only the bonus characters have some double meaning phrases but avoiding those you should be safe. :)
If you are interested in getting all the achievements be aware that there's 1 grindy and 1 grindy+luck-based one and 10 out of remaining 16 that are totally luck-based, requiring you to assemble a specific insult. Good luck with that, as doing it alone will probably get boring quickly. So far I've been able to get only 4 of those the easiest ones; and I've composed 2-3 of them while playing alone in couch-coop to make sure I was able to get all the parts =P and I don't think I'll be going for the rest anytime soon.

The Hollywood Roast adds some feature but generally continue improving what already done.
The game shifts from that generic british aura we've seen so far to a more, as you can guess, hollywoodian one. Characters may in fact remind you of famous characters you may have seen in movies =P
One of the first thing you may notice here is that now you can see points awarded to each (part of the) insult. You can see them only after you completed your insult (they appear as soon as each part is said by your character) like before, but now you have this sort-of breakdown which could help you understand what is considered funnier.
They also added a special Comeback, which get charged by your opponents' succesfull attacks. It comes in three variants: weak, medium and strong. I've seen the strong one scoring up to 18, which I believe is more than you can score with the best of your sentence. Sadly, you'll rarely have the chance to unleash it against CPU.
You'll also notice that now places and characters in single player are tied together: you don't know who's your next opponent but you'll meet them always in the same place.
I felt like there are a bit more parts with a double-meaning, but nothing too explicit imho. I giggled everytime I created an insult regarding my long, firm, staff.
On the achievement side, you can see that luck-based ones have disappeared to leave place for singleplayer ones. There's just one that could be tagged as luck-based, all the other are more to the grindy side.

More about points: I think in the Insult Simulator an insult couldn't score less than 4 (maybe even 3, but I may be mixing the games) while in the Hollywood Roast you can score as low as 1. They say that too-nonsense insults are bounded to score lower than "sense-full" ones. What I've noticed is that it doesn't seem to exist a connection between the different part of your insult; I mean, you could say «Your x did this thing with y and/but like to do something else.» and those two sentences could even be stating one the contrary of the other but you'll still get points for both. At least, I didn't notice any sensible penality while creating such insults.
So, base score for an insult vary from 1 to 15 (never seen an higher score), with a multiplier of 1.5 in case it contains your enemy's weakness and an ever-increasing multiplier in case of a combo (it starts with ×2, then ×3 and so on I guess, never reached ×4).
Stack those cleverly and you'll get huge scores! [proof] :D
Fail to complete a sentence though and you'll get 0, so watch out wheter to add more to your sentence or just stop.