In the fifth and final season of “Hacks,” it’s revealed that it’s always been DJ’s (Kaitlin Olson) dream to go on “The Amazing Race” with her mother, Deborah Vance (Jean Smart). In real life, the HBO Max comedy’s crossover with the long-running CBS reality series was a dream come true for the creators of “Hacks.”
“I love ‘The Amazing Race.’ I’ve been a huge fan of the show for a long time,” Lucia Aniello, one of the show’s three creators, told TheWrap. “We’ve always flirted with the idea of what it would be like for Deborah to go an ‘Amazing Race.’”
“The Amazing Race” got a shoutout on “Hacks” before. In Season 2, Deborah watched the show with her writing partner and eventual best friend Ava (Hannah Eininder). And after Variety’s Michael Schneider introduced the “Hacks” team to “Amazing Race” co-creator Elise Doganieri, the dream crossover morphed into a reality.
Directed by Jeff Rosenberg and written by Pat Regan, “D’Amazing Race” follows Deborah and DJ as they partner up to compete on a celebrity edition of the beloved series, alongide reality stars like Property Brothers Jonathan and Drew Scott, “I Love LA” star Jordan Firstman and social media star Trisha Paytas. Host Phil Keoghan also made an appearance. Though Deborah is hesitant to participate at first, only using the reality show appearance to boost sales for her Madison Square Garden show, over time she comes to appreciate her daughter’s commitment to the game. By the episode’s end, Deborah and DJ’s relationship is the healthiest it’s ever been with Deborah admitting she’s been too critical of her daughter and standing in awe of DJ’s fearlessness.
“Kaitlin Olson is truly the funniest person on God’s green Earth. She’s so funny, such a good dramatic actor, and she’s so lovely to be around. Her talent is endless,” Aniello said. “For us to be able to mostly end DJ’s story through her going on ‘Amazing Race’ and Deborah coming to terms with the fact that she has misjudged some of DJ’s best qualities … It felt like, weirdly, the perfect match.”
It’s a heartwarming conclusion to Deborah and DJ’s story that required roughly three years of work, multiple filming locations and a dangerous stunt that involved a massive cheese wheel on a steep hill.
“They talked me down because I wanted to do a whole season of 10 [‘Amazing Race’] episodes,” Aniello joked.
“We could have had six seasons — ended it where we ended up but threw in a 10-episode arc,” series co-creator and star Paul W. Downs told TheWrap.
When production designer Rob Tokarz was approached about the episode, he knew his job was to make it look as close to an installment of “The Amazing Race” as possible. The “Hacks” team borrowed several elements from their production, using the actual envelopes and blue clue boxes that appear in the CBS series. The team also made sure the on-screen graphics matched those you would see on an episode of “The Amazing Race,” and a producer from the show consulted with the HBO team to ensure everything was accurate.

“What made it really great is that Jeanine Ringer — my art director — is a huge superfan of ‘Amazing Race,’ so we had our own little internal quality testing to make sure we were right,” Tokarz told TheWrap.
The episode even shows some of the people who are integral to making “The Amazing Race.” The camera operators who repeatedly appear throughout the episode actually work on the CBS series.
“They’ve never been on screen because they’re usually shooting the show,” Tokarz said. “It just made everything move in a very real way.”
Though Deborah and DJ’s leg of the journey is set in Mexico, all of the filming took place around Los Angeles and Canada. Most of the scenes were filmed in Santa Clarita and on the Universal Studios lot; the clown challenge was filmed in Riverside. As for the airport scenes, those were filmed in Ontario.
But there was one element that threatened to turn this dream-come-true into a nightmare — the cheese hill. One of the challenges that appears in the “Hacks” episode requires the in-episode “Amazing Race” contestants to rush down a steep hill while carrying massive wheels of cheese on their backs. DJ volunteers for the challenge, and at first it seems like she’s nailing it. But when Paytas (who plays herself in the episode) drops her wheel, her loose cheese trips DJ, gravely impacting DJ and Deborah’s chance of winning.
“The cheese hill was probably the biggest challenge. It was a matter of finding the right location that had a hill that was visually steep yet manageable for all of our stunt people, camera crew and everybody involved. We probably looked at at least a dozen hill locations. It was a very heavy hiking scouting episode,” Tokarz said.
Olson’s schedule made the time-intensive episode even more challenging. Between her leading roles on ABC’s “High Potential” and FXX’s “It’s Always Sunny in Philadelphia,” Olson is one of the busiest actors on the cast of “Hacks.”
“It was scheduled around her to make sure that she was able to do all the work that we needed to get done,” Tokarz said.
Then there were the logistics of the cheese hill challenge. The team had several conversations about what kind of cheese should appear in the episode, even researching Mexican cheeses so that what appeared onscreen would be accurate. Production settled on large wheels that looked like parmesan, using both real wheels of parmesan cheese and hollow ones that were filled with sand so that they would properly roll down the hill. As for the cheese carriers the contestants wore, production made three different kinds: custom-made real cheese holders, rubber ones so that actors wouldn’t hurt themselves while repeatedly carrying the wheels and breakaway carriers for Olson’s stunt.
“The director of that episode, Jeff Rosenberg, told me he took something like 28,000 steps that day,” Tokarz said.
But ultimately, tackling the episode proved to be a triumph for both Olson and Smart. In a way, these two stars felt a bit of the excitement the average “Amazing Race” contestant feels.
“I was afraid I wouldn’t be able to do the physical things that were demanded,” Smart told TheWrap, noting she had just had knee surgery before shooting an episode that involved climbing several stairs and hills. “I just didn’t want to disappoint the director. But it worked out OK. Lots of times Kaitlin was helping me without trying to look like she was helping. It was fun.”
“We were out in the middle of nowhere. It was like 95 degrees. It was appropriately miserable at times and just so much fun. It was incredible,” Olson told TheWrap. “I’ve watched ‘The Amazing Race’ on and off for years, so I was super excited to be a part of it, in a weird way, and also meet [host Phil Keoghan].”
“Hacks” releases new episodes Thursdays on HBO Max.


