Base game
- Platinum Trophy Earn all of the other trophies to unlock the platinum trophy 11.2%Very rare
- Classic Completionist Complete a full game of classic Pictionary 35.5%Rare
- Pictionary Maniac Complete a full game of Pictionary Mania 22%Rare
- Fun with the Family Complete a full game of Family Fun Mode 27.4%Rare
- Persistent Picturist Play 50 games of Pictionary any mode 11.3%Very rare
- Clue Master Create 20 Custom Clues 12.5%Very rare
- Gallery Showing Create 15 Free Draw images and view them in the slideshow 12.1%Very rare
- Figure Artist Create 10 Pictionary Man drawings 12.5%Very rare
- Put me in Coach! Use a customized Pictionary Man in a game 24.9%Rare
- Mind Reader Correctly guess the clue in record speed 64%Common
- Slow Poke Fail to guess a clue before time runs out 62.9%Common
- Bookworm Go through each page of the tutorial 57.8%Common
- Shutout Win every All Play square within one play session 15.1%Rare
- Stingy Win without letting the other team play 14.9%Very rare
- Come on Already Change the clue type a lot within one round of play 27.5%Rare
- Mega Maniac Land on 15 Mega Mania squares and correctly guess the clue 11.3%Very rare
- Committed Complete a full length 4 Team game without continuing 12.6%Very rare
- Picasso's Understudy Use every tool and color in one Free Draw session 11.8%Very rare
- Handy Man Use every tool and color in one Draw Round 11.5%Very rare
- Mine, mine, mine! Steal a clue from another team 16.1%Rare
- Picasso spend at least an hour on one Free Draw image 12.8%Very rare
- Prosperous Cheater Cheat through the game quickly 12.5%Very rare
- Quick hitter Play Family Fun with 10 minute time limit, low Draw Timer, and Tempus Fugit 11.9%Very rare
- Resourceful Play Family Fun with Ink Limit mode, Random selections, and All Clue Categories 11.6%Very rare
- Easy Peasy Play Family Fun with Junior Clues, bonuses on, penalties off, and Picturist Chooses 11.8%Very rare
- See no Evil Play Family Fun with the No Peeking modifier and the Lights Out Draw Mode 11.7%Very rare
- Expert Play Family Fun with low Draw Timer, Difficult Clue Category, Tempus Fugit, Penalties, and Rivals Choose 11.7%Very rare
- Hands On Guess 10 clues in Finger Painting mode 12.6%Very rare
- Reverse Engineer Guess 10 clues in Eraser Only mode 12.6%Very rare
- Sight Beyond Sight Guess 10 clues in Lights Out mode 11.9%Very rare
- Topsy Turvy Guess 10 clues in Which Way is Up mode 11.9%Very rare
- Cant Stop Wont Stop Guess 10 clues in Conveyor Belt mode 11.9%Very rare
- Switch! Guess 10 clues in Tool Confusion 12%Very rare
- Pointillism Guess 10 clues in Dots Only mode 11.8%Very rare
- Vertigo Guess 10 clues in Rotation Frustration 12%Very rare
- Blinded Guess 10 clues with the No Peeking modifier 11.9%Very rare
- Waste Not Want Not Guess 10 clues with the Ink Limit modifier 11.9%Very rare
- Switch Hitter Guess 10 clues with the Off Hand modifier 12.1%Very rare
- Shapeshifter Guess 10 clues using nothing but the Shapes Tool 11.6%Very rare
- Brushless Guess 10 clues using nothing but the Finger Paint Tool 12.9%Very rare
- Just Add Water Guess 10 clues using nothing but the Watercolor Tool 11.5%Very rare
- Guess What? Guess 10 Custom Clues 11.6%Very rare
- Minimalist Win a game using only one tool and one color 23.3%Rare
- I Meant to do That Win an entire game without using the eraser or undo 28.6%Rare
- Challenge Accepted Guess 10 clues using mixed Draw Modes 11.4%Very rare
Trophy names, descriptions and rarity come from PlayStation. Guides open on their authors' own websites.