Andy Cohen explores the major pop culture moments of 2008 from Britney Spears' epic breakdown to the Octomom scandal. With celebrity guests RuPaul, Wendi McLendon-Covey, and Rosie Perez, Andy and friends look at how Barack Obama's election led to our current political climate, and how the housing market collapse gave birth to today's sharing economy. Plus, Meghan McCain tells the never before heard story of the day Trump questioned her father's heroism.

Andy Cohen dives into the opulent 1980s to explore how the wealthy spent their fortunes on everything from limos and jets to extravagant weddings, and how that's influenced the ways the mega-rich spend their money today. With celebrity guests Susan Lucci, Jill Kargman, Amber Rose and more, Andy looks at how the gilded mega-mansions of the 80s created today's high-tech minimalist homes, and how the pricey plastic surgery of yesterday influenced the anti-aging treatments of today. Plus, the Real Housewives spill their pre-nup secrets!