Green’s Dictionary of Slang

1. anyone who uses wit, charm, intelligence to gain objectives, whether honestly or (more usu.) dishonestly; also attrib.

1997–2000		College Sl. Research Project (Cal. State Poly. Uni., Pomona) 🌐 Playa (player/playette) (noun) 1. A person who can manipulate people or things to his/her advantage. [...] 2. A person with one or more relationships with a different person at the same time. [...] 3. Male or Female that kicks wit someone else even while goin’ wit someone. [...] 4. Usually a male with many girlfriends.
1999		Guardian Rev. 23 July 13: I’m not lookin’ for no arrogant egotistical playa shit!
2000		Guardian Guide 22–28 Jan. 28: I’m The One Tru Playa.
2000		W. Shaw Westsiders 231: There is a fashion for making ‘R’-rated videos now [...] they project an appropriate ‘playa’ image.
2010		A. Steinberg Running the Books 175: Arlo, man, you’re okay [...] You’ an undercover playa - I like that.

2. a womanizer.

2001		Eble Campus Sl. Fall 8: playa – person, usually a male, who dates or sleeps with a lot of different people at once.
2003		50 Cent ‘In da Club’ 🎵 If you watch how I move you’ll mistake me for a playa or pimp.
2004		Eble Campus Sl. Apr.