- Some people really do read it for the articles: Playboy is actually one of the magazines that The Library of Congress funded having printed in Braille. In 1985 it was dropped from the list. In 1986 the funding was restored when it was argued in court that blind readers who use the Braille edition really do get it for the articles since the Braille edition contained no ads or pictures.
- Marge Simpson's November 2009 appearance on the cover makes her the first animated character to do so.
- From 1999 onwards, Playboy usually featured a WWE Diva posing nude. If she posed for the magazine it become tradition for her to have a match at WrestleMania. Upon WWE going PG in 2008, this was dropped. Divas who posed were:
- Sable was the first to do so in 1999. She appeared on a second a few months later. A magazine dedicated to her two pictorials was released later, making her the first woman in Playboy history to have three covers in one year.
- Chyna in 2000. She posed again in 2002 after she had left the company.
- Torrie Wilson in 2003.
- Torrie again in 2004 with Sable, becoming the first Divas to pose together.
- Christy Hemme in 2005.
- Candice Michelle in 2006. Candice had also posed back in 2002.
- Ashley Massaro in 2007. She had previously posed twice in 2003 and 2004 under the pseudonym "Ryan McKenzie".
- Maria Kanellis in 2008.
- Maryse and Taryn Terrell had posed before they were in the company.
- Trish Stratus, Lita and Stacy Keibler were all asked to pose but turned the offer down.
- Stacy Carter (The Kat) claims that she was asked to pose in 2001 but the deal was scrapped when she was abruptly released.
- A contestant on the first season of WWE Tough Enough Bobbi Jo stated that her main goal was to pose for Playboy.
- Banned In China: Plus India, Myanmar, Malaysia, Singapore and Brunei, and most Arab countries.
- Best Known for the Fanservice: The naked ladies were what the magazine was best known for.
- Dueling Products: With Penthouse, leading to the "Pubic Wars". And then came Hustler and its overtly graphic pictures.
- Fountain of Expies: As probably the most famous men's magazine of all time, there have been innumerable expies (with titles like "Playpen") throughout almost all media. Likewise, whenever the publisher of such a magazine is depicted, it will almost always be a pajama-wearing, martini-drinking knockoff of Hef.
- Idiosyncratic Cover Art \ Easter Egg: The Playboy bunny icon is hidden somewhere on every cover.
- It's Not Porn, It's Art: A common justification... including during the early days, with several lawsuits trying to ban the magazine as obscene content. (and considering how raunchy equivalents such as Penthouse and Hustler get, the magazine got a pass with this trope).
- Mundane Utility: That sample image test known as Lena originated from a centerfold.
Trivia / Playboy