Society & Culture

Characters

by Cloud10

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Latest episodes

Jill Ann Spaulding's Scandalous Mansion Tell-All

October 20, 2026 · 1 hr 0 min

Jill Ann Spaulding wanted nothing more than to grace the pages of Playboy magazine - and she was willing to do almost anything to make her dream come true. After committing to perfecting "the Playmate look," Jill Ann becomes a Cyber Girl…
Anna Nicole's Final Years - Part 2

October 13, 2026 · 1 hr 2 min

After years of legal battles, financial uncertainty, and being made into the butt of late night talk show jokes, Anna Nicole had the opportunity to reinvent herself once again. The Anna Nicole Show allowed audiences to fall in love - until…
Anna Nicole Smith's Rise to Stardom - Part 1

October 6, 2026 · 41 min

Nearly 20 years since her passing, the life and legacy of Anna Nicole Smith continues to play in the public's imagination. In this part, we're discussing the conflicting stories of her upbringing (was she really born in Mexia, Texas?) and…
Jo Collins: the Playmate sent to Vietnam

September 29, 2026 · 25 min

After a soldier on duty in Vietnam purchased a lifetime subscription to Playboy, the brand had to follow through on an offer made years prior - that the first issue of a lifetime subscription would be hand-delivered by a Playmate. Jo…
Shannon Tweed's Playboy Mansion experience

September 22, 2026 · 27 min

Shannon Tweed lived 14 months at the Playboy Mansion, 1981-1982, as Hugh Hefner's girlfriend. Her story begins on a mink ranch in rural Canada, and a string of odd jobs in her youth, that led to her winning Miss Ottawa beauty pageant and…

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what Izabella St. James really thought being Hugh Hefner's girlfriend

September 15, 2026 · 1 hr 1 min

Book club!! We're recapping and reflecting on Izabella St. James' memoir, Bunny Tales: Behind Closed Doors at the Playboy Mansion. As one of the girlfriends in the final group of seven, leaving just before the Girls Next Door era, Izabella…
The truth about Gloria Steinem's time as a Bunny

September 8, 2026 · 33 min

Gloria Steinem's 11-day undercover stint as a Bunny in Playboy's New York City club was the subject of a bombshell essay that changed her career. The impacts of her exposé absolutely impacted the Bunnies working across clubs - from the pay…
The Seven Girlfriends Era: a comprehensive guide

September 1, 2026 · 43 min

Hugh Hefner publicly dating multiple women was a smart way to get the public talking about him (and the Playboy brand) after his marriage to Kimberly Conrad. We're are overviewing the transition from the Brande/Sandy/Mandy group to the…
Elle Woods was everyone's friend

August 25, 2026 · 16 min

Legally Blonde is, on some level, a film about friendship - showing up for people in the way you'd want them to show up for you. As Elle Woods is navigating a new world that doesn't respect her, she is continuing to show up fully ... and…
Ultimate Girls Trip with Jill Badlotto

August 18, 2026 · 23 min

Jill Badlotto joins us to discuss the first two episode of Real Housewives Ultimate Girls Trip: Roaring 20th! We share opinions on the casting choices, confessionals, and drama we've seen so far. You can find Jill Badlotto across platforms…
Vanna White's forbidden Playboy cover

August 17, 2026 · 24 min

Vanna White, national treasure best known as the longtime cohost of Wheel of Fortune, had to pay her bills pre-fame with some jobs she isn't particularly proud of (like many aspiring stars!). In 1982, just before she landed her role on…
The Bentley Twins + the deadly jewel heist

August 11, 2026 · 23 min

Sandy and Mandy Bentley were two of the most iconic women of the late '90s, early 2000s - brought into the public eye as twins dating Hugh Hefner at the same time, during his first group of multiple girlfriends. We'll overview how Sandy…

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About the show

Diving deeper on the characters we love to consume! Laura Diez hosts guest conversations and shares stories exploring the portrayals of real people on reality tv, fictionalized women that stay in our memories, and pop culture legends. New episodes Tuesdays and Fridays.