Inside Hacks’ Amazing Race Crossover Episode w/ Director Jeff Rosenberg

Reality TV meets prestige comedy as Rob Cesternino sits down with Jeff Rosenberg, producer and director on Hacks, to break down the making of the show’s Amazing Race-themed season 5 episode. Rosenberg—himself a dedicated reality TV superfan—shares how the creative team brought the energy and authenticity of The Amazing Race into the world of scripted TV, blending hilarious challenges, familiar production quirks, and genuine fan appreciation.

Rob and Jeff dive into how Hacks’ creators became hooked on The Amazing Race, why the memorable cheese wheel challenge made the cut, and how working with the actual Amazing Race crew—including host Phil Keoghan—helped capture the right spirit. The conversation also peels back the curtain on how the episode built both emotional stakes and comedic beats, using reality tropes to deepen the relationship between Deborah and her daughter DJ.

Highlights from their discussion include:
The story behind selecting iconic Amazing Race challenges like the cheese wheel and goat milking, plus the logistical hurdles of recreating them for scripted TV.
Cameos from the Property Brothers, NBA champs, and more—what went into dreaming up and casting a celebrity Amazing Race lineup.
The process of blending Hacks’ sharp comedy and heartfelt storytelling with classic reality show dynamics.
Real fan moments, including DJ’s tribute to how The Amazing Race helped her through tough times—mirroring the real-life impact these shows have on viewers.
Honest talk about strategy, challenge selection, and near-misses both on set and in the Amazing Race universe.

How does a show like Hacks pay tribute to—and poke fun at—Survivor, Big Brother, and Amazing Race while crafting its own story? Could a future celebrity Amazing Race really work, and would Jeff or Rob survive it? Explore the wild ride behind Hacks’ hit episode and the reality TV obsessions fueling it.

Catch the full conversation for behind-the-scenes insights, fan debates, and more reality TV crossover fun!

Chapters:
00:00 Jeff Joins for Hacks/Amazing Race
06:12 Amazing Race Easter Eggs Revealed
10:30 Shooting Hacks Like Reality TV
12:02 Ava Almost Ran the Race
15:14 Property Brothers and NBA Cameos
18:13 Phil’s Humor Shines On Set
23:08 DJ’s Emotional Race Superfandom
24:18 Iconic Cheese Challenge Chosen
28:05 Kaitlin Olson’s Goat Milking Scene
31:56 Deborah and DJ’s Elimination
37:08 Detour Decision and Fallout
40:19 Would Jeff Run the Race?
44:34 Survivor 50 and Fire Debate
48:33 Five More Hacks Episodes Coming

To pre-order Rob’s book, The Tribe and I Have Spoken, visit www.robhasabook.com

Never miss a minute of RHAP’s coverage!
LISTEN: Subscribe to the podcast feed!
WATCH: Watch and subscribe to the podcast on YouTube
SUPPORT: Become a RHAP Patron for bonus content, access to Facebook and Discord groups plus more great perks!