Oh...Sir! The Insult Simulator - Walkthrough overview
Hello! Welcome to the True Achievements walkthrough for Oh....Sir! The insult Simulator. I will do my best to guide you through this relatively simple completion, however I must warn you now: there are several chance/luck based achievements in this game. I can't control if you find these first try, or seven hours after trying to get them. Due to this, the time to complete the game can range from roughly 5 hours to well over 20 (worst case if you are the unluckiest person on this earth). Also, you will need to play the tournament mode a grand total of 6 times to unlock everything (Yaaayyy). Thankfully, this is relatively easy, and each playthrough will take 30-45 minutes or thereabouts.
With all that said, onto the next page!
Oh...Sir! The Insult Simulator - General hints and tips
The gameplay in and of itself is relatively simple. You will face off in bizarre situations against another character in the game. In the middle of the both of you is a table with several words/phrases on it. You will each take turns picking words from this table to construct insults. You will learn the best tactics as you go along on how to construct sentences that will deal the most damage. I will post a guide I wrote a while ago with a list of character weaknesses to help. For example, if you insult the fat guy on his weight, he will be more offended and therefore lose more health. Saying something rude also gives a bonus to damage. Using the same word in consecutive insults will give a combo and thus more bonus damage. Additionally, the longer the insult, the more damage it'll do.
Note: On the bottom of your side of the screen will be a teacup with 2 words/phrases in it. These are reserved for you and only you, so the opponent can't steal those. I suggest using them as a fallback so if you find your sentence is becoming a mess, you have a backup. This could be the result of the opponent stealing a good word from you.
Controls:
Use 
to navigate the word menu
to pick words
and 
to use teacup words
to end your sentence
to refresh the teacup with 2 new words (in case the 2 you have are either used or not good)
That should cover it all control wise. On with the show, because I don't exist!
(^you'll understand that one after playing. I promise ;) )
Oh...Sir! The Insult Simulator - Character weaknesses
This is a list of all the character weaknesses I could find within the game. I wrote this entirely myself and posted it as part of a solution on TA, but I will re-post it here for simplicity sake. Whenever you face off against a character, please read about them on this page to learn how to quickly defeat them. Definitely read about Father because he is the hardest character to beat in the game.
Sir Knight
Anything to do with modern times:
-Never watched Star Wars
-Still use/uses Windows Vista
-Don't/Doesn't own a colour telly
-Have/Has only local multiplayer
-Can be found in Pokemon GO
-Play/Plays hidden object games
and anything of a similar nature.
Mr j. Shufflebottom
His weakness is anything to do with style:
-Your hat
-Wear/Wears second-hand clothes
-Put/Puts on granny's clothing
-A cheap suit
-Homeless man's socks
-Have worse hair than
-Can't Tie a Tie
-Your sense of style
Nigel H.
Anything to do with weight and appearance:
-Your face
-Is/Are getting fat
-Is/Are dull and ugly
-Will always be alone
-Can't exercise because of
-A grunting sow
-An English Pig Dog in
-Always Be Alone
Mrs. Maggie
Anything about her age:
-Is/Are old
-Is/Are deceased
-Is/Are stone dead
-Is/Are no more
-Will soon kick the bucket
-Tell/Tells dirty jokes at funerals
Grisha
Anything to do with countries and communism:
-Your country
-Is/Are not a part of Europe
-The communists
-You commoner!
-Born In
-Uneducated Nincompoop
Albert
Anything to do with money/wealth:
-Is worthless
-Doesn't own a colour telly
-Made A Poor Deal With
-Your Kettle
-Homeless Man's Socks
-A Cheap Suit
-Wears Second-Hand Clothes
-Uneducated Nincompoop
-Your House
-A Commoner
H. P. Lovecraft
Anything about reality/being real:
-This Conversation
-Can't Tie a Tie
-An Ordinary Pigsty
-Has Bad Breath
-Is Rather Plain
The serious Sam character, the Postal dude, and Lo Wang never appear in the tournament mode from what I've deduced and thus their weaknesses are not listed here. If you wish to read up on them, consider the following link to a Steam Guide written which includes them.
https://steamcommunity.com/sharedfiles/filedetails/?id=83068...
Anyway, the final and definitely most important character list on this page is for Father. In tournament mode, he always appears last (Scenario 5). He has more health than you (hence the grey sub bar at the beginning on top of his health). At first, I found him rather difficult, but eventually I realized attacking his weakness is the only way to go about beating him.
Father
Anything to do with family:
-Your mother
-Your father
-Your sister
-Your son
-Your wife
-Your husband
-Your beloved auntie
Oh...Sir! The Insult Simulator - Luck based achievements
Before starting, I will discuss the luck based achievements. Some of these appear quite frequently, while others just don't come in much at all. It can be rather frustrating and boring but don't lose faith; they'll unlock in due time.
NOTE: While mentioned later, this deserves restating here and covers really everything on this page. You should consider knocking these achievements out using a second controller in local matches. This can remove the "luck" associated with having your AI opponent not steal words you need to create the achievement phrases.
NOTE 2: Do not have a second account signed in when going for these or any achievements. A second controller, yes, but take care to ensure there isn't an account logged in with that controller, or else that account may unlock the achievements you are trying to unlock instead.
Be on the lookout for the word Satan. No matter what, use this word when you find it as you have to use it 6 times for an achievement. Upon the 6th use, you'll unlock:
Now it's time for the real luck based ones. These are the achievements with their respective phrase/word divisions, as well as locations/characters needed to unlock or that increase the likelihood of the proper words showing up:
You/ still use Windows Vista:
This can be unlocked on any map with any character. Probably the easiest of the lot to find.
Your mother/ was a hamster:
This appears the most on "Pet Shop" using Nigel and Shufflebottom.
ClassicCompose a phrase with "Your mother is your father".
Your mother/ is/ your father:
These phrases can be found pretty much everywhere as well. Another one of the common ones.
Say No MoreCompose a phrase with "Your wife is interested in photography".
Your wife/ is interested in photography:
This one is apparently very hard to unlock. I believe I got lucky with it however, as it unlocked during one of my mandatory Tournament playthroughs.
This appears most often on "Pet Shop" using Nigel and Shufflebottom. It also has been reported to unlock on "By the lake" using Maggie vs Maggie.
You/ are silly:
Another common one. Can be found on any level with any character.
It's ElementaryCompose a phrase with "A duck hunter probably murdered this poor man".
A duck hunter/ probably murdered/ this poor man:
This one is rather annoying. Only found on "By the lake". Sir Knight and Maggie seem to be the best characters to make this one pop.
The B WordCompose a phrase with "Your country is not a part of Europe".
Your country/ is not a part of Europe:
Can be found anywhere, however it's best to use Grisha. His weakness is country and origins, making this one much more likely to rear its ugly head during battles involving him.
Your son/ died/ because of your sins:
This one is found on Heaven, using Father and Father. This is why you'll have to play through tournament 6 times. You can try and do this in tournament mode, but it's so much easier to do this with a second controller. I recommend that over trying to get it to show up against an AI. This removes the risk of stealing a part of the phrase or killing you in the process.
Your hovercraft/ is full of eels:
The worst one by far is Dirty Hungarian Phrasebook. This took me hours to get, and as far as I can tell, it takes everyone just as long to get. This will be the one to kill you out of all of them. Be warned, it is quite rare, so when you see the phrase, jump on it.
It shows up on "By the lake" and "ER" using either Maggie and Maggie or Shufflebottom and Nigel.
Copy these words in their divisions down, so you don't have to keep flipping through the guide to find them. Please take care to try and spot these as you play, otherwise you'll just have to grind later to get them. This is annoying. Very, very annoying.
If you find the first part of the phrase, keep hitting (...) and try and get the other part of the phrase. Pretty much every single one of these unlocked for me by doing this. It's pretty rare to find these groups all together at the same time.
With all of this finally out of the way, let's get down to business, pardon my french!
Oh...Sir! The Insult Simulator - Story walkthrough
To start off, load up the game to the main menu. Press "insult your CPU!", then go down to "Tournament". You should get a prompt basically asking you if you would like to do the tutorial. Accept it. If this prompt doesn't show up, then back out of Tournament real quick and press "Learn to insult" 2 lines up. There is an achievement for playing the tutorial.
This will unlock as soon as you start. No need to continue the tutorial if you don't want to. You can exit out now to the main menu. (Withdraw. Of course!)
Now go to Tournament. (for real this time 
). In order to unlock everything as quickly as you can, you'll need to play with 5 different characters. Personally, I chose Sir Knight as my first playthrough character. Upon picking him, you will see Scenario 1/5 pop up. Press this. You will now be in a real argument! Unfortunately, I can't give a step by step precise description of how to cream the character you are against, as the whole game is random. Just look for that characters weaknesses on a previous page and use that against them. In all honesty, this isn't even needed as the first 4 characters are fairly easy to defeat.
Anyway, once you win your first argument, you'll unlock:
As a side note, if you lose an argument, worry not! You can retry from that fight onward with no penalty. You can even exit the match instead of taking the time to die out. Then press Tournament again, choose the same character, and you'll be able to continue the same tournament from where you left off.
Now, continue on through the rest of the scenarios and keep on the lookout for the list of phrases needed for the achievements (as well as the word Satan).
Eventually, you will stumble onto the last scenario: Heaven, with Father as your opponent. This is where the headache starts if you aren't prepared. As mentioned previously, this is where you should really focus on attacks based on the characters weaknesses. Father is weak to the following:
-Your mother
-Your father
-Your sister
-Your son
-Your wife
-Your husband
-Your beloved auntie
(Anything to do with family really)
It may seem annoying at first, but once you get him good on the family thing he's as good as defeated. He has more health than you so if you don't use his weakness against him, it'll come back to bite you in the long run. Also, figure out what weakness your character has so that he doesn't use it against you either for huge damage. Be careful with the word "And" because he uses it as fast as he can. This can quickly mess up a decent sentence you're working on.
Even if it takes a few tries, you'll eventually beat Father (that'll put you in a good place on his books...RIP) unlocking:
And now you get to do it all again!
You will have to play through with different characters each time. After this run, you will unlock Nigel H. Play through the second time using him, and you'll unlock Grisha, netting you:
After that, you'll have to play 3 more times (again with a different character each time). After the fifth run through the tournament, you'll unlock:
This will give you the character Father. Finally, for the last time, you'll have to play tournament again, USING FATHER, to unlock the Heaven scenario. This is not mandatory, however it makes getting one achievement much easier (as described on the previous page), so I strongly recommend it.
Once the 6 runs are done, you can now start grinding out the rest of the game. I strongly recommend a second remote, however there is an online mode that will also make do. I have no idea if unlocking a phrase achievement will work for both players or not, so you will likely need to be the one hurling the insult to get the achievement in an online match. Using a second controller, even if the controller not assigned to your account gets a phrase, will still unlock the achievement. This is seriously helpful to reducing the randomness.
By now you should definitely have:
If you don't, worry not as you'll get it soon enough.
Before you start the grinding, head on with a friend or a second remote, for the following achievement:
This is very easy. Just keep using words like "Your mother" "and" your mother" "and". pretty much use a noun, then add on to it with "and" (or any word like it). When you run out of words to add on, press "(...)". This will make you keep the sentence until the next round. If you don't have it on the round your on, then sorry but you'll have to try again the next round. Keep adding on until you run out of the (...) options (when they stop showing up) and you can't add on anymore to the sentence. If you still didn't get it, figure out the character you're up against's weakness, then try again and exploit. It's really not that hard, but could take a couple tries to get the sentence pieces to work out.
Now, i recommend that you go for:
You will have a chance to get the random phrase achievements, as well as knocking down matches you need to play anyways. What I did was when the match loaded, I checked through both character's teacup options, as well as the word board to check for an achievement sentence. Depending on the words, I pressed or began to build the sentence on my main account. This will then shift it over to the other person, who will (as you should know by now) have 15 seconds to make a choice on a word to pick. Let the timer run out. They'll take 3 damage. Let it run out again. 12 damage. Again. 24 damage. And finally, one last time, 48 damage, and that's the game. Each match will last roughly 2 minutes total this way. Just make sure to search everyone's word listings so that you don't miss out on an a chance for the phrase achievements.
Once all this is finally done, there's a chance you'll still might be missing some of the phrase achievements. What I did to grind these out was:
1. Went on the appropriate map I needed to unlock these on.
2. Scrolled through the word list and once I concluded the word wasn't there, I pressed on both remotes.
This makes the round go by so you can keep looking for the words without getting damaged. I had a match last around 4 hours while trying to get one of the lines to pop up. This makes it so you won't have to keep resetting the match, and you'll be most efficient in finding the phrase you need.
If you have any more questions I didn't answer, please read the luck based achievements page. Otherwise, ask me in the forum so I can help you. As long as you don't give in to the RNG system and pray to the RNG gods, you'll get this game done eventually.
Happy hunting, hunters ^.^