Diving Bored Podcast

Naomi vs. Tyra: genuine feud or media fueled conflict? Join Jill and she deep dives one of the most notorious feuds in the history of the fashion industry. We discuss the "cat fight on the catwalk" that set Paris ablaze, the infamous sit down on the Tyra Show, how the press fueled the tension, and EVERYTHING in between. We also continue to ponder the question that rocked daytime televisi...

In 2003, Demi Moore and Ashton Kutcher sent shockwaves through Hollywood when they debuted their unlikely romance. What was originally thought of as a cougar publicity stunt, turned into one of the most serious celebrity couples of the 2000s. Join Jill as she deeps dives all the twist and turns of one of the most notorious couples of the 21st century. From "MOD" to Kabbalah, we cover eve...

Before fashion influencers, before Instagram, before sponsored posts...there was Rachel Zoe. Rachel Zoe didn’t just style celebrities, she helped shape how fame, fashion, and visibility worked in the 2000s. Join Jill as we unpack Rachel’s rise from behind-the-scenes stylist to cultural power player, the paparazzi era she mastered, the Zoebots, the weight-scandal scapegoating, and how her clients b...

This is a story about a girl named Britney...and Kevin. Join Jill for Part 2 of the Britney and Kevin saga. No stone goes unturned as we discuss Britney's journey through 2007 and 2008, her conservatorship, and how she persevered to gain freedom. She's stronger than yesterday, and now it's nothing but her way. We also ask Kevin to put his thinking fedora on to answer some hard hitting questions! D...

It's getting hectic in here, it's getting chaotic. Diving Bored is back! And to commemorate the momentous occasion we're diving into two of the biggest star crossed lovers of our time: Britney Spears and Kevin Federline. In this two part series, we will dive into everything. From the Chaotic era, to the conservatorship, no stone will go unturned. Join Jill as she dives into the relatio...

Feel the rain on your skin, we are officially deep diving one of the most infamous couples of our time: Spencer Pratt and Heidi Montag! We discuss it all. From their individual backstories, to them wreaking havoc all over Hollywood together, we pay homage to two of reality TV's original villains. We also discuss their recent redemption arc and how friends of the past are rallying in support. W...

Check underneath the tree because a new gift awaits, in the form of a deep dive on one of the biggest icons of our time, Mariah Carey. There are no reindeer games on this holiday episode, as we unpack it all. From Mariah's humble beginnings, to the Glitter fiasco, to one of the greatest comebacks of the 21st century, she is truly the gift that keeps on giving. So make your list and check it twice,...

In 2003, Nicole Richie premiered on our television screens in The Simple Life and became a household name sooner than you could say "sanasa". But as Nicole's fame grew, life became not so simple. Join Jill as she dives into Nicole's early years, her meteoric rise to fame, 2000s toxic tabloid culture and so much more. Jill also does several dramatic reads including one on the iconic Memorial Day pa...

Let me hear you say "yeahhhh boi!!" We have our first ever interview on the Diving Bored podcast and we're starting off as strong as ever with the iconic and legendary, Flavor Flav! Join Jill as her and Flav kick back and discuss everything from Public Enemy to Taylor Swift. We also discuss hip hop's early days, Flavor of Love, the US Women's Water Polo team and so much more! Get your clocks ready...

We've been on the run, driving in the sun, looking out for number one, Mischa Barton here we come. In 2003, Mischa Barton launched into superstardom when she starred as Marissa Cooper in the uber popular teen drama, The OC. On the outside it looked she had it all, but in reality it wasn't all sunshine. Join Jill as she deep dives Mischa's rise to fame, how art imitated life with her LA...

In the early 2000's, Tara Reid was the ultimate girl next door and It Girl. But when she wasn't ruling the silver screen, she was ruling every club in Hollywood. It wasn't long until Tara got the reputation of the party girl and things soon turned into Taradise Lost. We'll discuss Tara's rise to fame, her party girl image, how the press owes her an apology, and how she may be e...

Join Jill for the ultimate Jon & Kate Plus 8 deep dive! In the 2007, Jon and Kate Gosselin became reality TV pioneers with their first-of-its-kind family reality television show, Jon & Kate Plus 8. The couple and their eight children quickly became a gold mine for TLC, but it wasn't long until the cracks started to show. We'll discuss...literally everything. This insanely thorough...

In 2006, Flavor Flav screamed "yeahhh boiiii" outside a limo window and into our hearts when vh1 launched the wildly successful "Flavor of Love". The show launched and revitalized careers alike, as millions of viewers tuned in each week. Like they were the teacups at Disney World, the shows kept spinning, producing dozens of spinoffs with no end in sight. But it wasn't long...

It's Diving Bored Halloween and to observe the occasion Jill is telling the story of one of Hollywood's most notorious unsolved mysteries. In 1981, Natalie Wood had it all: fame, fortune, Robert Wagner. That all came to an untimely end one unfortunate night on the Splendour when Natalie disappeared. Join Jill as she discusses that night on Robert Wagner's boat, what him and Christopher...

Come on to my house, to my house, I'm gonna give you the longest episode ever of the Diving Bored Podcast. Join Jill as she submits her dissertation to earn her PhD in the Girls Next Door. No stone goes unturned discussing the complicated dynamics of two of our favorite Playboy bunnies. We'll discuss their life and times inside the mansion, Holly's bombshell tell-all memoir, Kendra&#39...

In 2005, Katie Holmes jumped on the back of Tom Cruise's motorcycle and straight into Scientology when they embarked on their whirlwind celebrity romance. What Katie didn't know, was that she may have bitten off way more than she could chew. We'll discuss their quick journey to the altar, their eventual divorce, and how Katie Holmes was able to outsmart Tom Cruise, Scientology and prob...

What ever happened to predictability? The milkman, the paperboy, the Olsen Twins on our TV? Mary Kate and Ashley hit the scene in the late 80's and over the next 20 years became megastars that shaped millions of childhoods worldwide. Join Jill as she deep dives the story of two of the biggest icons of our time. We'll discuss their Full House beginnings, their road to building their DualSta...

While Sydney Sweeney and Glen Powell gallivant under the Australian sun, we can't help but feel a scandal is afoot. After all, we're experienced veterans with this type of situation, which came in the form of one of the biggest Hollywood Scandals of the 2000's: Brangelina. Join Jill as she deep dives the origins of the one of the most infamous celebrity couples of our time. We'll d...

London is calling and so is the next pop culture deep dive! This week we cross the pond to discuss one of the biggest scandals to ever hit the fashion industry, and that is the story of C*caine Kate. We'll discuss Kate's groundbreaking career, nose candy scandal, and how she rebounded to make one of the greatest comebacks we've ever seen. So flag down the double decker bus, because it&...

It's officially Super Bowl Sunday and we are throwing a hail Mary pass to one of the most infamous Super Bowl moments of all time: the 2004 Janet Jackson Halftime Show. J*stin T*mberlake crooned "I'll have you naked by the end of this song", and in this case, he meant it literally. We'll discuss how 1/3 of a second worth of #Nipplegate spawned new terms in the English languag...

Happy Holidays everyone! There is no room at the inn, and while the three kings bring gold, frankincense, and myrrh, I deliver to baby Jesus what I do best: a story on a Hollywood scandal. For today's bonus episode we discuss the prince of Christmas movies himself, Macaulay Culkin, his incredible career in the 1990s, and the fortune he amassed as a result. However, even though he is one of Hol...

Semisonic once crooned "every new beginning comes from some other beginnings end" and it is now apparent they were referring to the Diving Bored Lindsay Lohan series. As we enter into the final part of the Lindsay series, we chronicle Lindsay from 2020 till now and how true comeback is only beginning. We'll discuss her new music and movie, upcoming projects, and where we want to see Lindsay go in...

On Part 4 of the Lindsay Lohan series, Lindsay officially enters her Valerie Cherish era and starts to plan her comeback. But instead of buckling down, she wreaks havoc on a Paul Schrader film and tries even Oprah's patience. We'll discuss the attempted comeback, her relocation to Europe, her strange new accent, viral dance moves, and even the time she tried to kidnap a child. Grab yoursel...

In part three of the Lindsay Series, we find LiLo in the midst of tailspin. Her career is flailing, her sobriety is questionable, and her sticky fingers are landing her into even more hot water. We'll discuss Lindsay's various strange projects during the late 2000s, her tumultuous relationship with DJ Samantha Ronson, and her many, many, MANY arrests. Get the bail money ready, because we're still...

Jill is back with Part 2 of the Lindsay Lohan series and things are heating up for LiLo. With her incessant club hopping and late nights, we soon find Lindsay's career is in danger. We'll discuss Lindsay's lifestyle as the top LA party girl, her times at the Chateau Marmont, the scolding letter from a movie producer (including a dramatic read), and a chronicle of her very first arrest. So sit down...