If you’ve already binged your way through Paramount+‘s fantastic new docuseries The Real Wolf of Wall Street that we included in last week’s roundup, then now is the perfect time to take a dive into the streamer’s vault as we unearth some juicy and controversial shows from not too long ago that still make for compelling weekend viewing.
This weekend’s picks, in order from most to least sensational, include a page-turning look into tabloid history from those who made it what it is, helicopter cops chasing bad guys through Florida swamps, and a devastating cultural reckoning with a fallen icon.
1
Gossip
Tabloid history from the queen of dish herself
As a still-recovering celebrity journalist for Hello! Magazine (a thousand years ago), I have firsthand experience with the gross and grimy world of gossip rags, so a lot of this four-part Showtime docuseries was a bit triggering, but still fascinating.
Before TMZ and Deuxmoi, there was the New York Post’s legendary celebrity gossip column Page Six. Gossip, from director Jenny Carchman (The Fourth Estate) and executive produced by none other than Ron Howard and Brian Grazer, charts just how digging up celebrity dirt became such big business. Through its hand-wringing, hour-long episodes, Gossip examines the rise of tabloid media, hinged on Rupert Murdoch’s purchase of the New York Post in the mid-’70s. It addresses America’s (and the world’s) insatiable appetite for “love, lust, money, crime, scandal, and death,” anchored by the Post’s legendary columnist Cindy Adams. The unapologetic firebrand—still gossiping at 91 when the series aired—gets the lion’s share of screen time through archival clips dating back to the 1960s and new interviews from her home office, alongside a who’s-who of fellow columnists and media insiders.
The celeb-stacked four episodes—featuring long-stale, but still iconic scandals involving everyone from Paris Hilton and Britney Spears to Donald Trump—trace the industry’s arc from Murdoch’s Post takeover through the tabloid TV era to the internet age, when bloggers like Perez Hilton rewrote the rules entirely. Guilty-pleasure gossip hounds will find this insatiable.
Gossip
- Release Date
-
2021 – 2021-00-00
- Network
-
Showtime
- Directors
-
Jenny Carchman
2
Chopper Cops
Real airborne pursuits over Central Florida, no reenactments needed
Your true crime pick this weekend trades shootouts and interrogation rooms for high-altitude awe-inspiring aerial footage, courtesy of the Marion County, Florida, Sheriff’s Department’s elite helicopter unit.
Chopper Cops follows that unit, known as Air One, as they respond to high-action, real-life emergencies across Central Florida, in helicopters equipped with all kinds of kit—from infrared cameras to augmented-reality mapping tech that let officers on the ground see in the dark. Led by Sheriff Billy Woods, the flight crews serve as the eyes in the sky for SWAT teams and ground units below. The action in each episode is captured and packaged using in-chopper cameras, radio comms, and first-person interviews with the officers and support personnel involved—no reenactments, just amazing raw pursuit footage.
Quiz
Summer 2026’s hottest new documentaries
Trivia challenge
From Wall Street scandals to pop legends — how much do you know about this
summer’s must-watch docs?
True CrimeMusicSportsHollywoodFinance
Paramount+’s The Real Wolf of Wall Street focuses on which convicted fraudster at
the center of the Stratton Oakmont scandal?
Correct! Jordan Belfort, the self-styled ‘Wolf of Wall Street,’ ran
Stratton Oakmont and was convicted of fraud and money laundering. The Paramount+ documentary revisits
his story beyond what was depicted in Martin Scorsese’s famous 2013 film.
Not quite. The documentary centers on Jordan Belfort, the notorious
stockbroker whose Stratton Oakmont firm bilked investors out of hundreds of millions of dollars. Bernie
Madoff and Ivan Boesky were separate high-profile Wall Street criminals.
In The Real Wolf of Wall Street, Stratton Oakmont was notorious for using which
illegal sales practice to inflate stock prices?
Correct! Stratton Oakmont used a classic pump-and-dump scheme,
artificially inflating the price of penny stocks through aggressive sales tactics before selling their
own shares at the peak, leaving investors with near-worthless holdings.
Not quite. The firm’s signature crime was the pump-and-dump scheme, in
which brokers hyped up cheap penny stocks to unsuspecting investors, drove the price up, then sold their
own shares for enormous profit. Ponzi schemes and insider trading are distinct types of securities
fraud.
The Real Wolf of Wall Street documentary on Paramount+ includes testimony from which
type of key sources to help reexamine the Stratton Oakmont story?
Correct! The documentary draws on accounts from surviving victims of the
fraud, former Stratton Oakmont brokers, and law enforcement investigators, giving a fuller and more
grounded picture of the scheme than Belfort’s own self-promotional memoir.
Not quite. The film incorporates perspectives from victims who lost
money, former brokers who worked at the firm, and the investigators who brought it down — offering a
counterpoint to the glamorized version of events that Belfort himself has often promoted.
HBO Max’s Marc by Sofia is a documentary about fashion designer Marc Jacobs directed
by which filmmaker?
Correct! Sofia Coppola, the acclaimed director behind films like Lost in
Translation and The Virgin Suicides, directed Marc by Sofia, offering an intimate portrait of her
longtime friend and fashion icon Marc Jacobs.
Not quite. The documentary is directed by Sofia Coppola, the
Oscar-winning filmmaker known for her visually lyrical style. Her personal friendship with Marc Jacobs
gave the film an unusually candid, behind-the-scenes quality.
Marc by Sofia on HBO Max primarily explores Marc Jacobs through which lens?
Correct! The documentary offers an intimate look at Marc Jacobs’
creative process and personal journey, including his struggles with addiction and recovery, his
identity, and what drives his singular artistic vision in fashion.
Not quite. Rather than focusing on business or legal matters, Marc by
Sofia takes a deeply personal approach, exploring Jacobs’ inner world, his sobriety journey, and the
emotional fuel behind his influential career in fashion.
Netflix’s Chris & Martina: The Final Set documents the legendary rivalry between
Chris Evert and Martina Navratilova. How many times did the two face each other in their careers?
Correct! Chris Evert and Martina Navratilova faced each other an
extraordinary 80 times over their careers, making it one of the greatest rivalries in tennis history.
The Netflix documentary revisits their competitive and personal relationship as both faced serious
health challenges.
Not quite. The two icons met a remarkable 80 times in their careers,
with Navratilova holding the edge in their head-to-head record. The Netflix doc frames their rivalry
through the lens of friendship and mutual support as both women confronted cancer diagnoses.
Netflix’s Michael Jackson: The Verdict examines public and legal reactions to the
allegations against Jackson. What major legal moment does the documentary reference as a turning
point in his legacy?
Correct! Jackson’s 2005 criminal trial, in which he was acquitted on all
counts of child molestation, is a central legal moment the documentary examines. The film explores how
that verdict shaped public perception and the ongoing debate about his legacy.
Not quite. The documentary focuses heavily on the 2005 criminal trial
acquittal as a defining legal moment, while also weighing it against the renewed allegations brought by
the 2019 documentary Leaving Neverland and the court of public opinion.
Peacock’s documentary Lorne is a profile of which legendary television producer?
Correct! Lorne Michaels, the Canadian producer who created Saturday
Night Live in 1975 and has shepherded it for nearly five decades, is the subject of Peacock’s
documentary simply titled Lorne. The film digs into the enigmatic figure behind one of TV’s most
enduring institutions.
Not quite. The Peacock documentary profiles Lorne Michaels, the famously
private and influential creator of Saturday Night Live. Despite shaping American comedy for generations,
Michaels has rarely spoken openly about himself — making this documentary a rare glimpse behind the
curtain.
Your Score
/ 8
Thanks for playing!
I’m stunned it took me this long to find Chopper Cops, but it’s made for some highly entertaining evenings watching fleeing criminals lit up by night vision and on camera as they try to hide under boats, scramble through swamps, and even escape through wildfires. Chopper Cops has two seasons and 20 episodes total, each around 30 minutes
Chopper Cops
- Release Date
-
June 18, 2024
- Network
-
Paramount+
3
We Need to Talk About Cosby
A filmmaker’s unflinching reckoning with a fallen icon
If Netflix’s recent wave of celebrity-reckoning docs like Michael Jackson: The Verdict and Sean Combs: The Reckoning hooked you, this one from 2022 still belongs at the top of the pile. With a Rotten Tomatoes score sitting at 99%, director W. Kamau Bell’s We Need to Talk About Cosby has been widely praised for letting the conversation get uncomfortable, resulting in a deep examination of the disgraced legendary entertainer and the culture that enabled him.
Broken up into four parts, Bell, a comedian and TV host, weighs Bill Cosby’s groundbreaking accomplishments against the more than 60 women who accused him of drugging and sexually assaulting them. But Bell doesn’t take the typical chronological route through true-crime territory—this isn’t a tracing of a career from rise-up to fall-down, like so many other bio-docs. We all know who Cosby is and what he did, and the series lets us start from there.
Building the story through interviews and his own voice-over, Bell uses archival footage that reveals a man at odds with his “America’s dad,” Cliff Huxtable persona. Most compelling are the firsthand accounts from several of Cosby’s accusers—including survivor Victoria Valentino, whose harrowing and emotional account closes episode one. Comedians, cultural commentators, and journalists round out the interviews. The series was nominated for four Primetime Emmy Awards. It’s heavy, but essential viewing.
Real stories for the weekend
Whether you’re in the mood for old-school tabloid gossip and its origins, a tough but necessary conversation, or sirens at 500 feet, you’ve got a few solid picks for your weekend documentary viewing. For more picks across every service, check out the How-To Geek streaming section.
- Subscription with ads
-
Yes, $8/month
- Simultaneous streams
-
3
- Live TV
-
Select live sports (NFL on CBS & UEFA Champions League)
- Price
-
Starting at $8/month or $60/year
Stephan is the sports journalist for the Maple Grove Report.
