- O'Neill Gang
- Oak Hill (Mafia)
- Oakwood
- Oakwood (Mafia)
- Oakwood Church (Mafia)
- Office of Price Administration
- Oh Boy!
- Oh Marie
- Oiseaux des Iles
- Old Dockworker
- Old Empirical Beer
- Old Farm
- Old Ford Bridge
- Old Man's Perils
- Old Observatory
- Old Service Station (Mafia)
- Olivia Marcano
- Omerta
- Omerta (Mafia)
- On the Road Again
- On the Trail
- One
- One Bourbon, One Scotch, One Beer
- One Careful Owner
- One Good Turn
- Ooh Baby Ooh
- Open the Door, Richard
- Operation: Deep Sleep
- Operator
- Ordinary Routine
- Ordinary Routine (Mafia)
- Orgy Warehouse
- Oscar
- Otis Redding
- Otis Spann
- Our Good Friend
- Out for Justice
- Out for No Good
- Oyster Bay
- Pablo Duarte
- Pachuko Hop
- Paddy Wagon
- Pagani's Fine Motors
- Page Creation Criteria
- Page Creation Tool
- Paint It Black
- Palermo Club
- Palermo Club (Mafia)
- Palisades Park
- Paradiso Hotel & Casino
- Parish Pride Mobile Homes
- Parry Betting Office
- Parry Bus
- Parry Bus (Mafia: DE)
- Parry Bus (Mafia II)
- Party Pooper
- Pasadena AR30
- Pass the Potcheen
- Paul Ghiringhelli
- Paul Revere & the Raiders
- Paul Scannapieco
- Paul Simmons
- Paul Tassone
- Paulie's Apartment
- Paulie's Apartment (Mafia)
- Paulie (Mafia)
- Paulie Lombardo
- Pearl Diver Motel
- Pedal to the Metal
- Peetie Wheatstraw
- Peggy Lee
- Pennies From Hell
- Pennies from Heaven
- Pennies from Heaven (Crosby)
- Pennies from Heaven (Prima)
- Pepe
- Pepe's Restaurant
- Pepe's Restaurant (Mafia)
- Pepe (Mafia)
- Pepe Gambino
- Pepé Costa
- Per Aspera Ad Astra
- Pere Sanglant
- Perfect Waffle
- Perks in Mafia III
- Perla's Nightclub
- Perla Robinson
- Pete Santini
- Petrol Head
- Phil Idrissi
- Picture Book Connoisseur
- Pictures of Matchstick Men
- Piece of Cake
- Piece of My Heart
- Pierced Heart
- Pinkerton Titan
- Pipe
- Places of Darkness
- Platinum Trophy
- Playboy Magazines
- Playboy Magazines (Mafia II)
- Playboy Magazines (Mafia III)
- Pocket Revolver
- Pointe Verdun
- Police
- Police Bus
- Police Bus Theft
- Police Dispatcher
- Police Officers (Mafia)
- Police Officers (Mafia: DE)
- Police Officers (Mafia II)
- Police Officers (Mafia III)
- Pompeii Bar (Mafia)
- Pop, Pop
- Pops Holland
- Porn Studio
- Port
- Port Bourbon
- Port of Lost Heaven (Mafia)
- Post Cards
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