Despite being passed over twice by Flavor Flav on the hit VH1 show Flavor of Love, everyone could see Tiffany Pollard, aka 'New York,' was a star. The self-proclaimed "HBIC" went on to have a slew of shows of her own and is central to some of the most memorable memes in history. Sydnee Washington, Marie Faustin, and Columbia University Professor Racquel Gates get to the bottom of why we STILL love New York. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In 2004 rapper Flavor Flav and actress Brigitte Nielsen confused everyone when they fell in love in front of cameras on VH1's absurd reality show, The Surreal Life. The romance gave rise to the spinoff, Strange Love. But once the couple broke up Flav went looking for love, competition style. The dating game show, Flavor of Love, saw 20 women vying for Flav's attention week after week and spawned an entire genre of D-list celeb-reality dating shows. Sydnee Washington, Marie Faustin, and culture writer Madeleine Davies re-examine what was so entertaining about dating D-list celebrities like Bret Micahels and Flavor Flav. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In the 80s and 90s the rap music scene was dominated by the East and West Coast. But in the early 2000s the Dirty South began to gain national attention, and in Houston, Texas, rappers created a unique sound of their own. Sydnee Washington, Marie Faustin, and Houston native Brandon Caldwell slow it way down to understand how chopped and screwed music made its way into the mainstream. Learn more about your ad choices. Visit podcastchoices.com/adchoices

For a long time supermodel Tyra Banks was known as the first Black woman to grace the cover of Sports Illustrated. She was a trailblazer in the modeling world. But Tyra had television aspirations and went on to host the now cringe-worthy America's Next Top Model and The Tyra Banks Show. Sydnee Washington, Marie Faustin, and Buzzfeed culture writer Michael Blackmon smize while unpacking the problematic television era of Tyra Banks. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In the 2000s a hit music video could make you a star. And for a time, the shows TRL and 106 & Park were THE places to see the most popular videos. Sydnee Washington, Marie Faustin, and co-host of NPR's Pop Culture Happy Hour Aisha Harris reminisce about the most memorable celebrity appearances, mishaps, and videos on TRL and 106 & Park. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In the early 2000s blogs were brand new, and one celebrity-obsessed troll combined the intrusiveness of the paparazzi with the nastiness of a burn book to create one of the most infamous gossip blogs of all time. Sydnee Washington, Marie Faustin, and the host of the Senior Superlatives podcast, Greta Titelman, unpack how Perez Hilton went from internet hater to hated on the internet.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

At the turn of the millennium, if you wanted an artist’s newest album, you almost certainly had to buy it from a physical record store. But by the early 2000s, two guys in their twenties upended the music industry with one of the most iconic peer-to-peer file-sharing services, Napster. Sydnee Washington, Marie Faustin, and the host of Broken Record podcast Justin Richmond go back to that strange time and question whether users were stealing music or just sharing it. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In 2004 during the halftime show of Super Bowl XXXVIII Justin Timberlake proclaimed he’d have you “naked by the end of this song,” and he wasn’t lying. No one remembers the outcome of the game because all anyone could talk about for weeks, months, and even years to come was how Justin Timberlake’s halftime performance resulted in 144 million viewers seeing Janet Jackson’s right nipple. Sydnee Washington, Marie Faustin, and comedian and host of the podcast Inside the Closet Matteo Lane break down how a millisecond of boob changed the world and Janet’s career. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Paris Hilton was “that girl” in the early 2000s. As an heiress and reality star, she helped give rise to the popularity of trucker hats, Juicy Couture tracksuits, purse-sized dogs, and the catchphrase, “That’s hot.” Sydnee Washington, Marie Faustin, and the host of the history podcast Not Past It, Simone Polanen, dissect how Paris Hilton became famous for being famous. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Back in the 2000s the aspiring dancer with a penchant for bad boys was a vibe… at least in the movies. Sydnee Washington, Marie Faustin, and The New York Times pop culture reporter Kyle Buchanan all hit the dancefloor to unpack Save the Last Dance, Honey, and Step Up. Learn more about your ad choices. Visit podcastchoices.com/adchoices