Playmate 9: After the brief shootout in the little book store, follow Joe through the door and up a tiny set of stairs. At the top of those stairs, you’ll find the next centerfold on the floor among a couple of boxes full of Playboys.
Playmate 2: Immediately after collecting Playmate 9, Joe will yell at you to follow him up a much larger staircase. Instead, head to the left of the stairs.
Turn right when you reach the entrance area, and you’ll see the next issue hiding next to the wall.
Playmate 8: After the shootout with the cops on the roof, follow Joe through this door:
Hang a left at the door and run straight ahead. The next issue is on the floor next to a set of shelves.
Playmate 7: After returning to Joe's apartment building, don't enter his place just yet. Instead, go down the stairs to that creepy-looking gate in the lobby. The next issue's waiting for you on the floor next to it.
Playmate 11: When Joe and Henry start charging downstairs at the beginning of the firefight, don’t follow them just yet. Instead, head upstairs.
You’ll find the next Playboy at the top of the stairs, next to an apartment door.
Playmate 10: As you reach the end of the first floor of the warehouse/distillery, you’ll see a little office on the left. After you’ve dealt with any nearby threats, go inside, because you won’t be able to do so on the way down.
Once you’re in, look to your right. The next issue is lying on a shelf.
Playmate 12: As you’re leaving the floor where Henry got wounded, keep an eye out to your right. The next issue is on the floor next to a couple of wooden chairs.
Playmate 13: After you’re finally set loose to explore the prison yard, take a look over to your right and you’ll see some bleachers set into an alcove.
Head around behind them and you’ll find a prisoner taking a nap. Your first piece of prison contraband is next to his feet.
Playmate 14: Head away from those bleachers and across the basketball court, and you’ll see a shed off to the left of the guard tower. Head toward it.
Walk over to the far side of the shed, and you’ll see the next issue:
Playmate 15: The next issue doesn’t show up until much later in the chapter, after you’ve fought your second real match in the laundry room.
Face the room's entrance (shown above), and then turn left. You’ll see the next issue sitting on top of one of the machines. Grab it before you go off to meet with your visitor.