Mafia 2 Playboy Magazine Locations - Chapter 14 and Chapter 15
Chapter 14: It's surprising, but there are only three playboys in this long chapter and they are all at the construction site.
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.