Introduction: The Jackbox Party Pack contains 5 games: You Don't Know Jack 2015, Fibbage XL, Lie Swatter, Word Spud, and Drawful. Each game has only 4 trophies associated with it. Even though these are party games meant to be played by multiple people, all trophies can easily be done by yourself and only one DualShock 4 controller is needed.
 
Any difficulty to be had comes from the YDKJ 2015: Winventory, but even that is negated if you use the full list of answers provided in this guide. Without it, it's still not that difficult as most of the Wrong Answers of the Game you'll have to pick are so obvious that you'll only miss them by instinctively picking a right answer when you see it before you take the time to look for what could be the Wrong Answer of the game. The only other trophy of any mild difficulty is Lie Swatter: Squish, Nothing But Wet, but if you take your time and search thoroughly before answering, even that should not be a problem.
 
All of the trophies here are online trophies. It is impossible to advance beyond the title screen without being connected to the internet and signed into PSN. Not even You Don't Know Jack 2015's single player option can be played without an internet connection. However, as you are not playing with or against other players over PlayStation Network, an active PlayStation Plus subscription is not required.
 
The bulk of the time to 100% comes from You Don't Know Jack 2015's YDKJ 2015: Winventory trophy. Each episode of the game takes roughly 13 minutes to complete if playing solo. For 50 episodes, that's about 10 hours and 50 minutes. Getting all the other trophies in the pack is fairly quick, taking roughly an hour to an hour and a half.

Each game uses smartphones, tablets, or computers as controllers instead of DualShock 4 controllers, which means you won't have to buy extra controllers to 100% this game. You also won't need other people to play with or even multiple devices. With a browser extension like Firefox Multi-Account Containers for Firefox, you can create and control as many players as needed from one computer.
 
When you install the extension, it will come with 4 containers by default: Personal, Work, Banking, and Shopping. Every container allows you one new player, so you will need to create 6 more containers. Click and hold on the new tab button (big + at the top of the window) until the Containers menu appears, then select Manage Containers. Underneath the list of containers you should see an Add New Container button; click it. Give the container whatever name, color (a unique color for each container is strongly recommended), and icon you like and then press Done. Repeat 5 more times and you should have 10 containers. 
 
With all your containers created, when you're ready to start a game with yourself, once again click and hold on the new tab button until the Containers menu appears. Select any of your containers to open a new tab in that container (you should see that the top of the tab has a color bar matching the color of the container). Go to jackbox.tv, enter your room code and player name, and sign into the game. Then repeat the process, creating new tabs in unused containers, to keep signing in more players as needed.

Minimum number of playthroughs: 51
Step 1: Play Episode 1 alone and get all the questions right. This step will get you YDKJ 2015: Drain the Main Brain and YDKJ 2015: Dat'll Do.
Step 2: Replay Episode 1 with two players this time, get the Wrong Answer of the Game, and have whichever player is losing after question 10 get everything right during the Jack Attack. This step will get you YDKJ 2015: Take It From Behind.
Step 3: Play the other 49 episodes, getting the Wrong Answer of the Game in each of them. This step will get you YDKJ 2015: Winventory.

Minimum number of playthroughs: less than 1
Step 1: Start a 3 player game. For the very first question, have one of the players enter "PICK ME" and the other two players enter the exact same thing. When picking answers, have the other two players pick the "PICK ME" answer. This step will get you Fibbage XL: Politician and Fibbage XL: Copycatfishers.
Step 2: For the second question, pause the game using the controller and then go to a search engine to find out what the right answer is. Have one of the players type this in as their lie. When picking answers, have all players pick the correct answer as you know what it is having looked it up. This step will get you Fibbage XL: Don't Know What To Believe Anymore and Fibbage XL: Truth Fairies.

Minimum number of playthroughs: 1
Step 1: Start a game, designating one player as "WINNER". Write in the instructions of what you're meant to draw rather than actually drawing anything for the entire game. You can get the trophies in whatever order you want over the three rounds of drawing, refer to the guide for details on each trophy. This step will get you Drawful: Goodfinger, Drawful: Show Me the Monet, Drawful: Schmuck of the Draw, and Drawful: "Art" Connoisseur.

Minimum number of playthroughs: 3
Step 1: Use Multi-Account Containers to create 10 different players. DO NOT START THE GAME. Name one player "WINNER" and another player "Sparkles". This step will get you Lie Swatter: Blufforgy and Lie Swatter: "What's My Name?" ft. Bugs.
Step 2: Clear out all players except for WINNER and one other player and start the game. For the first round, pause the game using the controller and look up whether the 7 statements are true or false. Have both players answer correctly, but have WINNER pick first to get a time bonus. This step will get you Lie Swatter: Squish, Nothing But Wet.
Step 3: Continue playing, although this time you can just guess. Have both players guess the same thing and have WINNER guess first for the time bonus if correct. Each game is 3 rounds, so you will have to play the remaining 2 rounds of the game from step 2 and then 2 more full games. This step will get you Lie Swatter: Tri-Swatter.

Minimum number of playthroughs: 4
Step 1: Use Multi-Account Containers to create 8 different players. DO NOT START THE GAME. Name one player "WINNER". This step will get you Word Spud: Word Herd.
Step 2: Clear out all players except for WINNER and one other player and start the game. Play one round and accept every word. Put in "nugget" as one of your words during this step. This step will get you Word Spud: Group Hug and Word Spud: Golden Nugget.
Step 3: Play three more rounds and intentionally reject one of the other player's words every round so that WINNER wins them all. This step will get you Word Spud: Spud Stud.