The following guide details how to easily unlock all achievements in the game in chronological order. Nothing is missable; you can redo all achievements through chapter select. Also, unless written otherwise, both players earn the achievement at the same time. This game can only be played with two players (offline and online) -- there is no single player mode. Note: The times listed below corresponds to the time the achievement is covered in the video below.
1. The Dip - 0:05 - Chapter: Escape - The Yard: Leo must do 20 dips in a row in the prison yard.
2. Freedom - 2:00 - Chapter: Escape - Prison Escape: Free the caged parrot in the warden's office.
3. Take A Breather - 2:38 - Chapter: Fugitives - Breather: At the start of the chapter, walk to the right. There is a rock both players need to sit on to enjoy the view.
4. Take It For A Spin - 3:45 - Chapter: Fugitives - The Farmstead: Climb the windmill and interact with it a few times to spin it up.
5. In Sync - 5:00 - Chapter: Fugitives - The Farmstead: Go into the house of the old couple. Vincent must play the piano and Leo the Banjo. Each player must hit 20 notes in a row without missing a single one. If one player messes up, you have to get another 20 correct notes.
6. Timeless Treasure - 6:40 - Chapter: Fugitives - The Farmstead: Go into the house of the old couple. On the ground floor is a clock; both players must interact with it at the same time. This opens a secret door upstairs; go into that hidden room to collect a sword from the chest.
7. Home Run - 7:48 - Chapter: Preperation - Reunion: At start of the chapter, go to the right. There is a guy with a baseball bat. Talk to him and then try to hit a home run. Swing the bat as soon as the pitcher starts the throw-animation. You must hit the ball in a straight line over the fence really far away. This only unlocks for the player getting the home run; the other player has to do it again.
8. You Started It - 8:41 - Chapter: Preperation - Reunion: Both players need to sit on the swing set at the same time.
9. No Cheating - 9:45 - Chapter: Preperation - Reunion: Talk to the woman with the baseball bat in the starting area of the chapter. Then, go to the trailer to her right side to find her husband. Talk to her again to get the achievement.
10. Backseat Mechanic - 11:50 - Chapter: Preperation - Reunion: Vincent must bring a wrench to the woman repairing a bike. Then, help her start the bike. Leo should stay inside the trailer until the achievement unlocks and not progress any further.
11. Managed Anger - 13:04 - Chapter: Preperation - Violent Questioning: Talk to the guy on the chair and choose to push back the chair. Leo must then pick the purse from the table, drop it on the floor, and lean over the table. Vincent must then use an object to torture the guy, which triggers a dream sequence.
12. Live the Dream - 14:51 - Chapter: Preperation - A Nie Life: After riding the elevator, both players must sit on the couch in front of the TV. Watch TV until Leo falls asleep.
13. Break From Reality - 16:46 - Chapter: Vengeance - Lift Off: Both players must play the arcade at start of the chapter.
14. Mayday! - 17:15 - Vengeance - Lift Off: Leo must interact with the helicopter at start of the chapter.