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Phil Keoghan says ‘Hacks’ star asked to be on ‘Amazing Race’ during crossover episode — then backtracked

May 1, 2026
in News
Phil Keoghan says ‘Hacks’ star asked to be on ‘Amazing Race’ during crossover episode — then backtracked

Kaitlin Olson asked Phil Keoghan to be on “The Amazing Race” when they filmed the “Hacks” crossover episode that aired Thursday night.

“Kaitlin, who plays [Jean Smart’s] daughter, she had expressed some interest in going,” Keoghan told Page Six in an exclusive interview. “And I started talking through it all with her.”

But Keoghan, 58, said the “It’s Always Sunny in Philadelphia” actress backtracked once she heard “what’s really involved” in appearing on the CBS reality show.

Phil Keoghan on
Phil Keoghan exclusively told Page Six that Kaitlin Olson asked him to be on “The Amazing Race” when they filmed the “Hacks” crossover episode. Courtesy of HBO Max and photographed by Kenny Laubbacher
Kaitlin Olson and Jean Smart on
But Olson (seen above with Jean Smart during the episode) backtracked about going on the CBS reality show when she heard “what’s really involved,” Keoghan told us. HBO MAX

And Olson wasn’t the only person on the “Hacks” set who inquired about going on “Amazing Race.”

“Lots of people expressed an interest, even like crew and everything,” Keoghan told us. “And that is always a good sign.”

He continued, “I do get celebrities approach me and say that they want to be on ‘Amazing Race.’ And then I start to go through the logistics of what that is. Then once they hear a little bit more about what’s involved, they go, ‘Oh, really?’ You shoot 12 shows in 21 days?’”

“I’m like like, ‘Yeah, there’s no there’s no trailer. It’s not a lot of pampering,’” Keoghan added.

Kaitlin Olson and Jean Smart on
Keoghan also revealed that multiple crew members expressed interest in going on “Amazing Race” (Olson and Smart are pictured above in a scene from the crossover episode). HBO MAX
Jean Smart on
“Lots of people expressed an interest, even like crew and everything,” Keoghan told us (Smart is pictured above during the episode). HBO MAX

The new episode of “Hacks” features Deborah (Smart) and DJ (Olson) competing on a celebrity version of “The Amazing Race” against “Property Brothers” Drew and Jonathan Scott and influencer Trisha Paytas and her partner.

Keoghan makes a cameo — first to kick off the race at the starting line, and then to eliminate Deborah and DJ after they come in last place on the first leg.

The Emmy Award-winning host told us the idea for the crossover event came from “Hacks” creators Paul W. Downs, Lucia Aniello and Jen Statsky, who are all superfans of “The Amazing Race.”

Jean Smart and Carl Clemons-Hopkins Jr. on
The Emmy Award-winning host also said that the “Hacks” creators came up with the idea for the crossover episode (Smart and Carl-Clemons Hopkins Jr. are seen above). HBO MAX
Phil Keoghan on
Keoghan (seen above on “The Amazing Race”) said creator and star Paul W. Downs “was very keen on making it happen.” CBS via Getty Images

“The producers of ‘Amazing Race’ and ‘Hacks’ were at the same event, and that’s where the discussion was first had,” Keoghan explained. “The idea was floated out there, and then conversations started to happen. Paul was very, very keen on making it happen.”

Keoghan said when producers sent him the script, he gave them notes to make sure the “Hacks” episode was faithful to “The Amazing Race.’”

“I realized there were some things that I wouldn’t say. So I was a bit hesitant in the beginning to be like, ‘Do you mind if I change this?’ But they opened it up to being a collaboration. So I tentatively, with respect, [told them] ‘Could we change that?’ And they were like, ‘Oh, please!’”

Phil Keoghan attends the CBSFEST 2026-2027: Fall Schedule Announcement
Keoghan (pictured above at the CBSFEST 2026-2027: Fall Schedule Announcement) also confirmed that the “Hacks” producers let him edit the script for the episode. CBS via Getty Images
Kaitlin Olson attends The Walt Disney Company's Emmy Season Toast to TV
Keoghan added that his favorite part of shooting the episode was getting to work with Smart (Olson, who plays Smart’s daughter in “Hacks,” is seen above at DIsney’s Emmy Season Toast to TV event). Getty Images

But the “best part” for Keoghan was getting to interact with Smart, 74, when the cameras stopped rolling.

“Once we got a take done of any of the scenes that I was in, Jean would just start to riff,” he told us. “And I used to do improv theater. So I suddenly found myself just going back and forth with her.”

Keoghan added, “And it was a real thrill to just be in this surreal moment of having fun.”

The fifth and final season of “Hacks” airs new episodes on Thursdays at 9 p.m. ET on HBO Max.

The post Phil Keoghan says ‘Hacks’ star asked to be on ‘Amazing Race’ during crossover episode — then backtracked appeared first on Page Six.

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