[11] The Playboys began on the corner of Pico Boulevard and Fedora Street in Los Angeles County, in the mid 1950s.

Since then, members have moved to different parts of Los Angeles County like Burbank, North Hollywood and other cities in the San Fernando Valley.

In the beginning the gang was predominantly Hispanic, but in recent years, even though it is rare, other ethnic groups have been able to gain membership making them multiethnic.

Originating in the 1990s in Santa Ana and Garden Grove, the Orange County Playboys have established a presence and garnered respect both within and outside of prison over the years.

Despite efforts by law enforcement to dismantle the organization, the Playboys continue to grow in size, with an approximate 360 active gang members solely within Orange County.

[17] The Westside Playboys have cliques in Burbank, North Hollywood, Palmdale, Canoga Park and Lancaster, California, while the Southside Playboys have cliques in Ensenada, Mexico; Eugene and Portland, Oregon; Omaha, Nebraska; and Tacoma, Washington.

[15][25] They also engage in murder, drive-by shootings,[15][26] assaults and arms trafficking,[27][28] but most of their criminal activity is around the sale of marijuana.

All other cliques outside of Los Angeles engage mostly the street level distribution of narcotics as their main source of revenue.