Trivia: Best known for her ongoing association with Playboy -- as a centerfold and as one of Hugh Hefner's paramours -- Holly Madison enjoyed a childhood that witnessed her family moving between Astoria, OR, and a rural island off the coast of Alaska; the clan eventually settled in Oregon, and Madison enrolled in Portland State University, where she majored in psychology and theater. Halfway through school, however, she gravitated to Southern California (where she found the climate more appealing) and transferred to L.A.'s Loyola Marymount University, working as a Hooters waitress and a Hawaiian Tropics model on the side. A friend of Hugh Hefner's soon spotted Madison posing in a Tropics photo session, which prompted Hefner to place her on the guest list for the annual Midsummer Night's Dream party; eventually, Hefner asked her out on a date and made her his "Number One Girl." As such, Madison moved into the famous Playboy mansion and received prominent billing on the popular E! network reality series The Girls Next Door (2005) -- a candid, behind-the-scenes view of mansion life. In terms of big-screen work, Madison also landed a small role in Scary Movie 4. After she and Hefner split, she continued her work on reality TV shows, with her own spin-off on E!, Holly's World, and a stint on Dancing with the Stars. She later took up residence in Las Vegas as the headliner for Peepshow, a burlesque show, where she performed for almost three years. In 2015, she appeared in the TV movie Sharknado 3.

Trivia: A name that carries its own connotations, Hugh Marston Hefner not only founded the billion-dollar Playboy Enterprises, but did much to spearhead the "sexual revolution" -- first by publishing Playboy magazine in 1953, then by expanding his girlie magazine into supper clubs, cable networks, book publishing, apparel, adult-entertainment home videos, and scores of other arenas. Playboy Magazine itself began with a well-known business coup: Hefner purchased nude photographs of an extremely young Marilyn Monroe and published them in his magazine, in December 1953, making the first issue an instant, must-have American phenomenon. This provided the necessary boost to get the publication underway. Whereas other purveyors of entertainment for men, such as Larry Flynt and Al Goldstein, would later hone in on the gritty underbelly of the market, Hefner aggressively (and successfully) attempted to make eroticism and nudity more palatable to average middle-class citizens, gradually bringing increasingly explicit printed material into mainstream America's living rooms and thus reshaping the country's moral and sociocultural landscape. To Hefner's credit, he never failed to underestimate the intelligence of his readers, filling each issue with the finest literary work, criticism, interviews, and nonfiction journalism, alongside his erotic centerfold photographs -- thus giving the magazine some class. Film historians might be intrigued to know that Hefner's cinematic activities are not by any means limited to softcore adult entertainment. He has occasionally produced critically lauded mainstream pictures, such as Roman Polanski's X-rated (for violence, not sex) Macbeth (1971), Arthur Hiller's cult classic The Crazy World of Julius Vrooder (1974), and (as part of a legal settlement) Peter Bogdanovich's extraordinary character study Saint Jack (1979).Hefner was portrayed by Cliff Robertson in Bob Fosse's Star 80, Jack Fitz in American Gangster, and Randall Batinkoff in the telemovie Hefner: Unauthorized. In the 21st century he was the star of the reality series The Girls Next Door, which focused on his relationship with three former playmates, and in 2008 he played himself in the Anna Faris comedy The House Bunny.

Trivia: A native of Southern California who was born and raised in San Diego, Playboy model and Hugh Hefner girlfriend Kendra Wilkinson attended Clairemont High School and then accepted a position as a dental assistant, when her photograph landed on Hefner's desk and caught his attention. A mutual acquaintance subsequently contacted Wilkinson on Hefner's behalf and invited her to attend his exclusive 78th birthday celebration as body-painted entertainment for the party. Not long after, Hefner invited her to move into the Playboy mansion as one of his girlfriends-in-residence, an invitation she promptly accepted. She then appeared as a centerfold in Playboy magazine and starred, opposite Hefner, Holly Madison, and Bridget Marquardt, in the E! network reality series The Girls Next Door. Wilkinson also appeared opposite Madison in the genre parody Scary Movie 4. She got her own reality show, Kendra, in 2009, and competed in the 12th season of Dancing With the Stars in 2011. In 2012, she left the E! network, launching a new reality show, Kendra on Top, on WEtv.

Trivia: A track star and an Olympic champion at the 1976 Olympics, the former Bruce Jenner parlayed athletic success into a career in media, working as a spokesperson and news correspondent and also working in movies for a brief spell. After some time away from the spotlight, Jenner was reintroduced to a new generation in 2007 as a participant in the E! Network reality program Keeping Up With the Kardashians. The program depicted candid events from the lives of Jenner's stepdaughters -- the biological children of third wife Kris Jenner and her first husband, the late attorney Robert Kardashian and eventually followed Jenner's own children with Kris - Kendall and Kylie.In a 2015 episode of 20/20, after months of speculation, Jenner came out as a transgender woman and later made her debut as Caitlyn on the cover of Vanity Fair magazine, with plans to appear in her own reality show, I am Cait, on E!