The BEST episodes of Generation Hustle

Every episode of Generation Hustle ever, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Generation Hustle!

How far would you go for power, fame and fortune? Featuring outrageous, high-stakes stories, each episode follows a brilliant and brazen young entrepreneur who uses cunning and creativity to pull off the most wildly inventive high-stakes gambles of the new millennium.

Last Updated: 12/30/2023Network: HBO MaxStatus: Ended
Hollywood Con Queen
46 votes

#1 - Hollywood Con Queen

Season 1 - Episode 1 - Aired 4/22/2021

Dreams and deception collide when a brilliant con artist impersonates high-profile Hollywood producers to scam aspiring young artists. After the FBI teams with a dogged investigator to hunt this fraudster across the globe, a twisted tale, reminiscent of classic caper movies, ensues.

Directors: Yon Motskin
Watch Now:Amazon
Frat Boy Ponzi
22 votes

#2 - Frat Boy Ponzi

Season 1 - Episode 7 - Aired 4/22/2021

Shortly after pledging his college fraternity, Midwest math whiz Syed Arbab uses funds raised from fellow students, alumni, and high school friends to start a hedge fund. Flush with cash, Syed becomes a campus legend, until a market crash causes his hedge fund (and life) to implode. As this stereotypical “good kid” breaks bad – trafficking cocaine, packing heat, and defrauding investors – the feds close in.

Directors: George Plamondon
Anna Delvey Takes Manhattan
34 votes

#3 - Anna Delvey Takes Manhattan

Season 1 - Episode 4 - Aired 4/22/2021

Aided by a masterful social media presence, the young, awkward Anna Sorokin transforms herself into glamorous German heiress Anna Delvey. But after she sticks her friend Rachel with the bill for their lavish vacation, Anna’s world begins to unravel and she goes on the lam. Convinced her friend is a con artist, Rachel works with the NYPD to piece together clues to track Anna down.

Directors: Martha Shane
Cult of WeWork
30 votes

#4 - Cult of WeWork

Season 1 - Episode 5 - Aired 4/22/2021

Is Adam Neumann a brilliant salesman or a greedy false prophet so charismatic that he convinced an entire generation to follow him to the promised land? The last of Silicon Valley’s so-called “unicorns,” WeWork’s extraordinary rise and fall is told through the eyes of some of the multi-billion-dollar company’s earliest disciples.

Directors: Yon Motskin
The Party’s Over
36 votes

#5 - The Party’s Over

Season 1 - Episode 2 - Aired 4/22/2021

Building a business with nothing but blind ambition, Ian Bick transforms himself from a nerdy teen into a concert promoter almost as legendary as the bands he books. As the teenager’s EDM raves pack houses and feed his emerging VIP lifestyle with first-class trips, high-end shopping, and brand-new jet skis, his fall is as dramatic as his rise – culminating in an FBI raid that shocks his family, friends, and hometown.

Directors: George Plamondon
Watch Now:Amazon
A Scam with a Beat
23 votes

#6 - A Scam with a Beat

Season 1 - Episode 10 - Aired 4/22/2021

A teenager reinvents himself as scam rapper Teejayx6, using his songs to teach others how to con. When his music takes off, the master of deception manages to scam his way into a record deal with one of America’s biggest labels before the age of 20. But as Teejay ascends, the real-life stakes increase.

Directors: Yemisi Brookes
The 23 Lives of Jeremy Wilson
29 votes

#7 - The 23 Lives of Jeremy Wilson

Season 1 - Episode 3 - Aired 4/22/2021

Jeremy Wilson channels his good looks and effortless charisma to assume many identities: a decorated Special Forces Captain, a swanky Scottish music journalist, the love child of an infamous IRA bomber, and more. While this master of deception travels the country seducing, manipulating, and cheating friends and family, he manages to evade law enforcement for decades – until he’s finally outsmarted by a New York City cop.

Directors: Jeremiah Crowell
Watch Now:Amazon
The Prince of Fraud
22 votes

#8 - The Prince of Fraud

Season 1 - Episode 8 - Aired 4/22/2021

An orphan born in Colombia and raised by his adoptive parents in Michigan, Anthony Gignac developed a taste for the finer things – and to get them he assumes the persona of a Saudi Royal prince. Whether flying high with real-estate moguls or convincing banks to extend him lines of credit, Gignac earns his reputation through a combination of wit and bravado… but how long can he sustain the delusion before the authorities catch on?

Directors: Jeremiah Crowell
Watch Now:Amazon
The Alabama Exit
19 votes

#9 - The Alabama Exit

Season 1 - Episode 9 - Aired 4/22/2021

When self-proclaimed Google alum Kyle Sandler bursts into the tiny town of Opelika, Alabama to launch the Round House business incubator, he promises to turn the town into the “Silicon Valley of the East.” The enchanted residents throw themselves into the project, until a local 14-year-old inventor gains nationwide press for reportedly rejecting a $30 million outside buyout offer. Spooked Round House investors are left wondering: is Kyle who he says he is or were his promises built on lies?

Directors: Martha Shane
Watch Now:Amazon
20 votes

#10 - Baekeland

Season 1 - Episode 6 - Aired 4/22/2021

Young, aristocratic billionaire William Baekeland charms his way into an exclusive group of wealthy world travelers – only to disappear with their money. Is he a brilliant imposter who spins fabulous lies and invents fictional personas to con the rich or just a kid who went too far trying to escape his past?

Directors: Yon Motskin