Midsummer Night's Dream Playboy Mansion Party 2014

- During the early 2000s, ESPN began broadcasting live boxing bouts from the large backyard. Vassiliy Jirov and David Haye are some of the notables to have fought there. Sugar Ray Leonard, in his capacity as boxing promoter, has held boxing cards there.
- In addition to numerous Playboy features and pictorials, the Playboy Mansion has been the subject of a coffee table book (Inside the Playboy Mansion, 1998, ISBN 1-57544-044-X), a video game (Playboy: The Mansion, in which the player must build the Playboy "empire"), and inspired the U2 song "The Playboy Mansion" on their 1997 album Pop. The Nightwatchman's song "One Man Revolution", contains the lines: 'On the streets of Havana/I got hugged and kissed/At the Playboy Mansion/I wasn't on the list'.
- The mansion featured in music videos including "Playmate of the Year" by Zebrahead, "Work It" by Nelly featuring Justin Timberlake, "Rockstar" by Nickelback, and "Beverly Hills" by Weezer. MTV aired a special in late 2000 where Limp Bizkit threw an album release party at the mansion to coincide with the release of their album Chocolate Starfish and the Hot Dog Flavored Water.
- In the 1987 Eddie Murphy movie Beverly Hills Cop II, his character, Detroit police detective Axel Foley, crashes a party at the mansion.