Pros
Playboy is a worldwide brand, with the rabbithead being recognizable on the level of the golden arches or the Coca-Cola logo. Working there has a certain woo-woo factor that easily impresses people -- it is considered a sexy, interesting company to work for. It is a very easygoing, casual atmosphere with a bred-in-the-bone healthy attitude toward a work-life balance.
Kontras
It has recently gone through an enormous upheaval at the top management level. It may be too little or too late. Playboy puts a premium on being a top-heavy organization and never saw a problem that it thought it couldn't solve with another Vice President, though that may be slowly changing with the new CEO. At the end of the day, Playboy is a family business and has deep idiosyncrasies at the DNA level that other publicly-held companies don't have.