Numerous videos have been released by Playboy Enterprises, the publishers of Playboy magazine. They are largely made up of music-video-style vignettes featuring Playboy Playmates and other models in various stages of nudity and, on occasion, softcore sex scenes.

The last Playboy home video to be released was the 2008 DVD 2009 Playmate Video Calendar.

The first videos released under the Playboy banner were issues of Playboy Video Magazine (also known as Playboy Video and Playboy Video Collectors Edition). Twelve issues were released in this series, from January 1983 to 1987. Early volumes on CED, laserdisc, and Japanese VHD, while all volumes appeared on Betamax and VHS. Issues contained content similar to the magazine; in addition to video pictorials of the Playmates, celebrities, and other models, segments on music, interviews with celebrities, comedy sketches, and other material was included (the format being similar to Electric Blue, a UK video magazine that aired on the Playboy Channel). Total running time of an issue is longer than other Playboy videos (80–90 minutes versus 35–60 minutes), but with a similar total amount of running time devoted to model pictorials.

Issue #1 is the first Playboy video to feature a Playmate of the Year (PMOY) (1982's Shannon Tweed), and the first Video Centerfold (Lonny Chin, Playboy's January 1983 Playmate). Other segments in the first issue are an interview with John and Bo Derek, an erotic fiction short, a documentary look at historic moments in Playboy, a pictorial of actress Barbara Carrera, a look at the Playboy Jazz Festival, comedy shorts from Michael Nesmith, and a pictorial of the Crazy Horse Saloon dancers.

In 1986, the Playmate calendar series began with a volume for the coming year, 1987. This series focused on the Playmates themselves and did not try to imitate the content of the magazine. Although the months assigned to the Playmates in the videos are not the same as the months in which they appear in the magazine, nearly all Playmates from 1987 on have appeared in a Playmate video calendar. Playmates of the Year have also appeared in a special individual video profiles.

Each video begins with the voice of Neil Ross, the narrator for most of Playboy's productions, saying:

The video profile of a Playmate is shot at the same time that her magazine centerfold and pictorial are photographed. These usually consist of three or four vignettes reflecting the personality and persona of the Playmate and an interview is also conducted at the same time to serve as in introduction to her viewers. Two of the vignettes are then chosen to be included as part of her video Playmate profile. The very first Playmate to appear in a Playmate video calendar was Cherie Witter, Miss January 1987 (Miss February 1985 in the magazine).

In the early video Playmate calendars, a significant amount of time was given to each Playmate to introduce herself, two or three minutes were spent on describing her aspirations and goals. This was then followed by a nude profile.