The BEST episodes of Dark Side of the 2000s season 1
Every episode of Dark Side of the 2000s season 1, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Dark Side of the 2000s season 1!
Dives into the unseen histories of the 2000s decade, revealing dark secrets and personal insights from the people who observed it all firsthand.

#1 - Charlie Sheen: Addicted to Winning
Season 1 - Episode 8 - Aired 8/29/2023
"Two and A Half Men" is a huge success until Charlie Sheen self-destructs; in a plot twist no one sees coming, he wages a public, hateful, and violent war against his producer.
Watch Now:Amazon
#2 - Shock Jocks Part 2: The Fall
Season 1 - Episode 6 - Aired 8/15/2023
Radio king Howard Stern continues to draw attention with his on-air antics; when Opie and Anthony resurface, their hatred for Howard isn’t enough to save the toxic friendship.
Watch Now:Amazon
#3 - Lindsay Lohan: Star, Interrupted
Season 1 - Episode 3 - Aired 8/1/2023
From child star to punchline, Lindsay Lohan may have lit the bonfire that burned down her life, but it’s the rise of the ravenous 24-hour gossip cycle that nearly eats her alive.
Watch Now:Amazon

#5 - Jon & Kate Plus 8: Family Circus
Season 1 - Episode 1 - Aired 7/18/2023
The Gosselin's marriage dissolves on TV. When the couple weaponize their fame in a messy divorce, they fracture the image of the perfect American family.
Watch Now:Amazon
#6 - Men's Magazines: The Maxim Effect
Season 1 - Episode 9 - Aired 9/5/2023
Men's magazines like Maxim inject new energy into the magazine industry, but they leave a toxic legacy in their wake.
Watch Now:Amazon
#7 - The Bachelor: Every Rose has Its Thorn
Season 1 - Episode 7 - Aired 8/22/2023
Part game show, part reality TV, and steered by producers willing to manipulate the truth and their participants, “The Bachelor” is a ratings machine.
Watch Now:Amazon
#8 - TRL: Last Request
Season 1 - Episode 2 - Aired 7/25/2023
TRL is the daily destination where celebrities and their fans mix, creating an unpredictable media circus where beefs, battles, and breakdowns turn into an awe-inspiring sideshow.
Watch Now:Amazon
#9 - Siegfried & Roy: Magic and Mayhem
Season 1 - Episode 10 - Aired 9/12/2023
Siegfried and Roy transform Vegas, only to have their careers end in tragedy; the truth of the 2003 tiger attack that nearly takes Roy's life is anything but straightforward.
Watch Now:Amazon
#10 - TMZ: Paparazzi Gone Wild
Season 1 - Episode 4 - Aired 8/8/2023
TMZ becomes the celebrity gossip machine; it’s raw, real, and above all, irresistible; success comes at a price that’s too high for some of its content creators.
Watch Now:Amazon