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Mafia 2 Playboy Magazine Locations - Chapter 9 and Chapter 10
Chapter 9: There are four playboys hidden in Chapter 9. Thankfully they're all along the main paths.
Playboy #23 is inside the sewers below the slaughthouse. You walk right past it during the slaughterhouse mission. Look into the short tunnel on the left after the pipe dumps a bunch of sewage onto Vito.
Playboy #22 is just inside the first part of the slaughterhouse. When you enter the furnace room with the sleeping worker, look to the left in the coal piles for this playboy.
Playboy #24 is found during the sneaking portion. After you go through the freezer and reach the butcher room (the one with the two butchers, some hanging pigs and a counter that you use for cover) look in the back corner past the hanging pigs for a magazine in a basin thing.
Chapter 10: There are another playboys in this chapter.
Playboy #25 is hidden in the laundry area. Once you go through, look for a room on the left side that says "Daily Room." Go through to find a desk with a playboy on it. You need to get it before you dress up in the uniform. If you get lost, then go forward until you find the guy that opens the gate. Instead of grabbing the uniform right away, back track past the elevators and look for the room on the back wall.
Playboy #27 is pretty easy to find. After you set up the bomb for Room Service and get into the staircase with Joe, go down the stairs. If you go down a few flights you'll find a cage looking thing. The playboy is lying next to the closed door inside.
Playboy #26 is literally in your path. It's by the window washing machine. Pick it up while you're waiting for the lift to come up.
Playboy #48 is inside the master bathroom (the one of the bedroom, not the one off of the hallway). It should be there after you finish the mission.
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Mafia 2 Playboy Magazine Locations - Chapter 11
Chapter 11: There are five playboys in this chapter and they're fairly spread out.
P layboy #47 is inside Leo's home. From the starting point, don't go further back into the house. Go back into the main hallway and look out through the front windows (you should actually see Henry coming in). Grab the playboy off of the windowsill.
Playboy #29 is right after #47. After you grab it off the ledge, walk through the door into the bedroom. Turn to the right to reach the laundry room and turn to the left to enter his bathroom. Grab the playboy while you're here.
Note that you might just want to grab the playboys on a repeat playthrough, since this method usually conflicts with getting "Wake Up Call." Henry usually found me if I took the logical route.
Playboy #28 is at Eric's party. When you enter, don't turn to the left for the real party. Just walk through and enter the bedroom. The playboy is right next to the guy on the floor.
Playboy #49 is available once you go to Joe's apartment after the attack on your home. It's lying next to Joe's new bed. Pick it up while he's talking to his contact.
Playboy #30 is at the Irish bar (Hill of Tara). After you clear the first room, run over to the bathrooms. Walk through the doors and pick up the playboy.
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Mafia 2 Playboy Magazine Locations - Chapter 12 and Chapter 13
Chapter 12: This has three very easy ones to find once you know that they're there. They're all in the Chinese warehouse area.
Playboy #32 is near the front of the yard. It's to the right as you walk through the gate (if you drove then you passed it. Go to the tanker and then look for a delivery truck over to the left. The playboy is on the ground behind it.
Playboy #31 is also in the main yard. As you go into the back alley with the guys, look to the right for a short side alley with a few dumpsters and a disgruntled worker. Walk to the far back corner and look behind the dumpster. The playboy is wedged behind it.
Playboy #33 is available after you make the deal. After you make it away from the first ambush, you'll cross a ramp and enter the lackluster cover of the side office. The playboy is on the ground on the right side. If you know to look for it as you go through, then it's easy.
Chapter 13: There are another three easy to find playboys in this combat mission.
Playboy #34 is on the upper level of the restaurant area. After you clear it out, go up the stairs but turn to the left. It's on a seat to the far back left.
Playboy #36 is in the large opium den that you reach after the fight through the kitchen. Look into the first little room to find it on a table.
Playboy #35 is right before the drug lab. If you're sneaking, then it's the spot where Joe beats up the guy quietly. It's in the side room with all the grenades and molotovs on a crate to the side.
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Mafia 2 Playboy Magazine Locations - Chapter 14 and Chapter 15
Playboy #44 is on the starting level of the construction site. After you escape and take out the guards, look for it in the back right corner of the site. It's in a little area by the second elevator space, close to the guard that moves around and doesn't just wait for you to push him off the building.
Playboy #37 is close to the second floor of the construction site. After you go down the stairs and trigger the fire that seals off the main entrance, look to the left for a playboy on the ground. Grab it before you slide over the obstacles with Joe.
Playboy #38 is just past #37. After you jump over the obstacles and take out the bulk of the guards, move over to the right side of the site. The playboy is lying on the ground in a corner of the side room.
Chapter 15: All four of the last playboys are at the planetarium. Pick them up as you go through the fight.
Playboy #45 is at the first spot where you enter the building. There's a chandelier and a man on the roof who will fire through the glass at you. After you take out the first group of guards, the resulting damage of the man falling should move the obstacles aside. Go down the steps until you reach a little room before. Grab the playboy.
Playboy #39 is on the rooftop just after #45. Once you go up to the roof and clear out the guards, approach the door to the real planetarium, but turn to the right. There's a little hidden niche in the corner at the front of the building that has a playboy on the ground. Grab it.
Playboy #43 is just past #39. After you enter the room with the giant telescope, walk around it and look for a playboy on the ground behind it. It's by the wall that prevents you from dropping off onto the stairs, if that helps.
Playboy #42 is in the real planetarium where you fight Falcone. After you kill Falcone, walk up to the projector in the center and enter the box. The playboy is on the ground right next to it. Grab it and walk out with Joe.
Congratulations! With this playboy, you should get the Ladies Man achievement (it takes a second for it to come up, so don't panic.