Oh...Sir! The Hollywood Roast is a relatively simple game to complete though it takes some luck and a decent bit of time.
Oh... Sir is a game where you go head-to-head with another person/AI and insult them by going back and forth choosing a phrase. Once you and your enemy end your sentences, they will deal damage to the other player. It does more damage depending on the number of insults in the sentence, how much it makes sense as an insult, whether or not it's a combo, and whether or not one of that character's weaknesses were attacked.
The trophies require you to beat the career mode 6 times while completing every challenge, winning a cliffhanger, winning a roast quickly, and doing a bunch of damage with a single sentence.
You will need a boosting partner for the 2 multiplayer trophies because the multiplayer was dead as soon as the game was released and you need to complete 65 matches.
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