Diving Bored Podcast
The podcast recorded from the rabbit hole. Take a break from reality and join Jill as she goes beneath the surface and deep dives all of your favorite pop culture moments from Y2K, the 90's, and beyond! Follow the podcast on Instagram @divingboredpod
Tue, February 18, 2025
Deep Dive: Spencer and Heidi
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. What will happen next? Well, the rest is still unwritten. Follow the podcast on Insta @divingboredpod Ways to Support LA Fire Victims: FireAidLA Global Empowerment Mission Los Angeles Regional Food Bank California Fire Foundation World Central Kitchen American Red Cross California Community Foundation
Mon, December 23, 2024
Holiday Deep Dive: Mariah Carey
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, because all I want for Christmas is a deep dive on the Diving Bored Podcast! Follow the podcast on instagram @DivingBoredPod! Happy Holidays everyone and a peaceful and prosperous New Year!
Mon, October 28, 2024
Deep Dive: Nicole Richie
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 party invitation. You are cordially invite to the deep dive of Nicole Richie! Follow the podcast on instagram @divingboredpod
Tue, May 21, 2024
Diving Bored Interview: Flavor Flav
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 and dive in with the greatest hype man of our time. Follow the podcast on Instagram @divingboredpod
Tue, May 14, 2024
Deep Dive: Mischa Barton
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 partying ways, and the trials and tribulations she's had to go through to become the women she is today. Dive into the twists in turns of another iconic It Girl of the early 2000s. Follow the podcast on @divingboredpod!
Tue, April 16, 2024
Deep Dive: Tara Reid
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 entering a second renaissance. #JusticeForTaraReid
Sun, February 04, 2024
Deep Dive: Jon & Kate Plus 8
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 dive touches on Jon and Kate's divorce, the haircut that launched a thousand Karens, Jon's party girl era, and so much more. So buckle that car seat, because this wild story may have you asking to the see manager. Follow the podcast on instagram @divingboredpod
Tue, December 12, 2023
Deep Dive: The Rise and Fall of the "Of Love" Dynasty
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 until everyone wanted off the ride. Join Jill as she deep dives the meteoric rise and crashing downfall of some of the shows that shaped our childhoods. So get your New York reaction gif ready, because you may be at a loss for words. Join the podcast on instagram @divingboredpod!
Tue, October 31, 2023
Diving Bored Halloween: The Unsolved Mystery of Natalie Wood
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 Walken might be hiding, and what Natalie may be trying to tell us from beyond the grave. Follow Diving Bored on instagram at @DivingBoredPod Special thank you to the multitalented Kyle Parker! Check him out on instagram at @kyleparkr
Thu, October 05, 2023
Deep Dive: Celebrity Feud: Holly Madison & Kendra Wilkinson
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's subsequent Twitter tirade, and so much more. Jill also releases a call to action that may change Diving Bored as we know it. So let's climb out of the rabbit hole and into the ring, because we're going multiple rounds discussing the decade long feud of our favorite girls next door. Follow the podcast on Instagram @divingboredpod
Thu, August 03, 2023
Deep Dive: Tom Cruise and Katie Holmes
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 probably even X*nu himself. We'll also discuss Jill's cyber feud with Perez Hilton as she unearths unfinished business to avenge Suri Cruise's honor. So join Jill as she dives into one of Hollywood's most infamous tales, and it just may leave you with more questions than answers. Follow the podcast on Instagram @divingboredpod!
Tue, June 06, 2023
Deep Dive: The Olsen Twins
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 DualStar empire, and how they've collectively built one of the biggest contemporary fashion labels of the last 20 years. You're Invited to Mary Kate and Ashley's deep dive on the Diving Bored podcast! Follow Diving Bored on instagram @divingboredpod!
Sat, May 06, 2023
Deep Dive: Brangelina
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 discuss the origins of the couple, their ever growing family, and the events that eventually led to the couple's demise. We also solidify our spot on #TeamAniston, and give a current update on Brad (let's just say it hasn't been his day, his week, his month, or even his year). "There are no regrets in life, just lessons" -Jennifer Aniston Follow the podcast on instagram @DivingBoredPod!
Sun, March 26, 2023
Bonus Deep Dive: Kate Moss
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's finally time for a deep dive on our favorite British icon.
Sun, February 05, 2023
Deep Dive: Janet Jackson Super Bowl Halftime Show
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 language, a groundbreaking website, and a new trajectory in Janet Jackson's career. We don't remember who won the game that day, but we do know we're #TeamJanet forever and ever. Follow the podcast on Instagram @divingboredpod!
Sat, December 24, 2022
Holiday Bonus Dive: Macaulay Culkin's Parent Emancipation
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 Hollywoods top actors, his money is in danger of getting stolen. (Spoiler alert: it's not from the Wet Bandits). We'll discuss his amazing films, emancipation from his parents, and where he is today. And we won't forget the milk, eggs, and fabric softener. Follow the podcast on Instagram @divingboredpod!
Sat, December 17, 2022
Deep Dive: Lindsay Lohan Part 5 (The Resurrection)
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 the near future. It is Diving Bored's sincere hope she just continues to share her light with us. Thank you all so much for listening to the Lindsay Lohan series and it has been my biggest joy to finally bestow this to the world. I can't wait to see what is next for our favorite red head. Join the pod on instagram at @DivingBoredPod!
Fri, December 16, 2022
Deep Dive: Lindsay Lohan Part 4 (The Comeback Era (sort of))
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 yourself an Aperol spritz, because this is how we party on the Diving Bored Podcast, bitch! Follow the podcast on Instagram at @DivingBoredPod!
Thu, December 15, 2022
Deep Dive: Lindsay Lohan Part 3 (The Spiral Continues)
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 just getting started. "I'm my own worst enemy, and I know that." -Lindsay Lohan Join us on instagram at @DivingBoredPod!
Wed, December 14, 2022
Deep Dive: Lindsay Lohan Part 2 (The Spiral Begins)
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 and buckle in, because Lindsay is about to take us for a 100 mph car chase down the Pacific Coast Highway and at the end of the day, we're just along for the ride.
Tue, December 13, 2022
Deep Dive: Lindsay Lohan Part 1 (The Early Years)
She's tired of rumors starting and she's sick of being followed. The time has officially come. The deep dive of our crowning jewel is here. Join Jill as she lays the ground work on the first installment of the long awaited Lindsay Lohan series. We'll discuss her early days, her meteoric rise to stardom and the beginning of her descent to becoming one of the most infamous tales in the history of Hollywood. "Normalcy is not interesting." - Lindsay Lohan Join us on Instagram! @DivingBoredPod
Sat, October 29, 2022
Diving Bored October: The Black Dahlia
Diving Bored October is back! This week Jill is deep diving the case of The Black Dahlia. We'll discuss the heinous crime, the tall tales revolving the case, and some of the potential suspects. Jill even says who she thinks committed the crime and what it'll take to solve one of Hollywood's most notorious Unsolved Mysteries. #JusticeForElizabethShort Follow the podcast on instagram at @DivingBoredPod
Tue, October 18, 2022
Diving Bored October: Haunted Movie Sets
Get the sage ready, because Diving Bored October is here! Join Jill as she recounts the most haunted and cursed movie sets of all time. From Poltergeist to The Exorcist, Jill dives into the harrowing stories of what happened while making some of the most iconic horror films of all time. Because after all, sometimes truth is scarier than fiction.
Tue, September 27, 2022
Deep Dive: Martha Stewart
Diving Bored is back! And Jill is ready to talk about the stock market to whoever will listen. Join Jill on Diving Bored's first Businesswoman Special deep dive on the notorious, Martha Stewart. Jill gets a workout in by stepping on several soapboxes while telling the incredible and scandalous story of one of the most successful businesspeople in human history. We'll discuss the rise of Martha's empire, the insider trading scandal, and how at 80-years-old, Martha continues to reinvent herself. This episode is dedicated to Martha's crocheted poncho and of course, businesswomen everywhere. "The more you adapt, the more interesting you are" -Martha Stewart Follow the podcast on instagram at @divingboredpod
Tue, July 12, 2022
Deep Dive Celebrity Feud: Paris Hilton & Lindsay Lohan
The year is 2006 and behind the doors of Hollywood's most exclusive clubs, a feud is a brewin'. Tinseltown's top party girls Lindsay Lohan and Paris Hilton are at odds and the fighting is ringing all through the Hollywood Hills. So let's pile into the front seat of the SLR and take a ride, because the flames of this feud will have you saying "that's hot".
Tue, May 24, 2022
Deep Dive: Anna Nicole Smith
In the early 90's, Anna Nicole sent shockwaves (and cars off the road) when she hit the scene as a model for Playboy and Guess? Jeans. Her beauty took the world by storm, but it was her marriage to a man 60 years her senior that made her an international sensation and the world's most famous "gold digger" gone wrong. Join Jill as she deep dives the origins of the Anna Nicole image, the infamous Marshall v. Marshall court case, the Anna Nicole show, and the subsequent legacy she's left behind.
Mon, May 02, 2022
Deep Dive: Ashlee Simpson
On a Monday I am waiting, by Tuesday I am fading, and by Wednesday I'm wondering what the hell ever happened to Ashlee Simpson? In 2004, Ashlee skyrocketed to fame (and out of her older sister's shadow) with her debut album and hit MTV reality show. But as Ashlee's road to fame was seemingly easy, she soon learned that life at the top came with its fair share of challenges. Ashlee went from fighting comparisons to her sister Jessica, to now fighting comparisons to the infamous Milli Vanilli. Join Jill as she deep dives the show, the SNL incident and aftermath, and the many twists and turns of Ashlee's life and career. So if you want her auto, want her autobiography, baby just ask me .
Sat, April 23, 2022
Deep Dive: Newlyweds Nick & Jessica
In the early 2000's, Nick Lachey and Jessica Simpson were the first couple of pop culture. Millions of people invited the couple into their living rooms each week through MTV's Newlyweds: Nick & Jessica. While they seemingly were on top of the world, the power duo soon started to crack. We'll discuss the show, the origins of reality TV and what eventually led to the pair's demise. Was it chicken? Or was it fish?
Tue, April 12, 2022
Deep Dive Celebrity Feud: Lindsay Lohan & Hilary Duff
The year is 2004 and two of Hollywood's biggest starlets are feuding. But what is making these two rising stars hate each other? Well, it's none other than the boy who beat Shaq, Aaron Carter. Travel back in time to one of the early 2000's strangest love triangles and celebrity feuds. The podcast of the month? Nah, the podcast of the year.
Wed, April 06, 2022
Deep Dive: The Girls Next Door
Come on to my house, to my house! The Girls Next Door premiered in 2005 and was an instant runaway hit. For the first time in history, viewers were able to get an inside look at life inside the most iconic party palace in the world, The Playboy Mansion. For years viewers saw Holly, Bridget and Kendra travel, go to mansion parties and live the 24/7 vacation life the mansion afforded them. Or so it seemed. What viewers didn't know at the time was that behind those steel gates, a controlling, demeaning and abusive octogenarian was making life hell. We'll deep dive the show, the three women's experiences at the mansion, and the incredible accomplishments they've made since getting out from under the Playboy thumb. Following @divingboredpod on Instagram!
Tue, March 22, 2022
Deep Dive: Winona Ryder Shoplifting Scandal
It's showtime! In the 1990's Winona Ryder was on top of the world. She was acting in dozens of films and was regarded as one of Hollywood's top actresses. So why on earth did she find herself in 2001 shoplifting at a Saks Fifth Avenue? Join Jill as she deep dives this iconic moment in pop culture and how it affected the course of Winona's career. Jill also dissects Winona's iconic courtroom looks. Because if you're going to commit a crime, it better not be a crime of fashion. #FreeWinona
Thu, March 17, 2022
Deep Dive: Amanda Bynes Part 2
This is the episode where we stop being polite, and start getting real. Join Jill as she takes on the twists and turns of the second half of the Amanda Bynes deep dive. This episode finds us discussing conservatorships, mental health and how changes are hopefully coming. Learn about the past events of Amanda's life and what leads us up to her conservatorship hearing on March 22nd. #FreeAmanda
Tue, March 15, 2022
Deep Dive: Amanda Bynes Part 1
In the 1990's and early 2000's Amanda Bynes had already established herself as the queen of Nickelodeon. With an adorable image and brilliant comedic timing, Amanda was positioning herself to become one of the most famous and longstanding actresses around. By 2010 however, we watched in real time the starlet buckle under the severe pressures of Hollywood. Join Jill as she deep dives all of the details on Amanda Bynes' journey and what led up to the conservatorship that Amanda is currently fighting to be freed from. #FreeAmanda
Tue, March 08, 2022
Deep Dive: Pam and Tommy Tape Saga
In 1995, Pamela Anderson and Tommy Lee were spontaneous newlyweds enjoying life together. Once their private home videos were stolen from their home however, their lives and society were changed forever. Join Jill as she deep dives the Pam & Tommy tape saga and how this little Hi8 tape worked to change the world.
Tue, February 15, 2022
Deep Dive: The Bling Ring
Join Jill on the pilot episode of the Diving Bored podcast and enjoy her inaugural deep dive on the iconic story of The Bling Ring. In this deep dive, Jill will share with you all the details the movies or books never told you. So call up Nancy Jo Sales and strap on your brown BeBe heels, its time dive into the sordid tale of Hollywood's infamous Burglar Bunch.
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