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Charlie Day reveals extremely awkward first day on movie set with Jennifer Aniston

Home> Entertainment> Celebrity

Updated 11:37 4 Apr 2026 GMT+1Published 11:35 4 Apr 2026 GMT+1

Charlie Day reveals extremely awkward first day on movie set with Jennifer Aniston

Both stars previously said they'd be up for revisiting the popular film franchise

Jess Battison

Jess Battison

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Cast your mind back to 2011, Jennifer Aniston is sexually harassing Charlie Day at work and Jason Sudeikis wants to murder Colin Farrell.

Yeah, that was the year of the release of Horrible Bosses, obviously.

Also starring Jason Bateman, Kevin Spacey and Jamie Foxx, the crime comedy film saw three mates conspiring to murder their horrific, abusive bosses.

It became such an iconic movie it was of course followed up by a sequel in 2014 but that did end up being a bit of an arguable flop. However, it seems like the case had a proper laugh during filming anyway, despite a rather awkward first day on set for Day.

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Playing dental nurse Dale Arbus, he’s victim to the sexual harassment of boss Dr. Julia Harris (Aniston).

Can't believe it's been 15 years since this to be honest. (Warner Bros.)
Can't believe it's been 15 years since this to be honest. (Warner Bros.)

Julia blackmails her subordinate quite a bit, making inappropriate advances and forcing him into acts.

As a resolution, Dale and his mates decide to try and kill her with Kurt (Sudeikis) even trying to sleep with her to divert her interest.

So, it’s fair to say, Aniston and Day had to film some rather interesting scenes together and get to know each other fairly well.

And the It’s Always Sunny in Philadelphia actor recently spoke about his time on Horrible Bosses during press for the new The Super Mario Galaxy Movie.

Joined by co-star Chris Pine, he was reviewing photos from previous on-screen roles for Entertainment Weekly when he was shown a snap of Aniston biting his ear.

Day joked that the moment was actually a ‘private photograph’ of the pair snapped by paps. However, it’s of course one of the many bizarre scenes from the film.

And this led Day to think back to one scene in particular; when Julia uses some revealing snaps of Dale as blackmail.

"Our very first day of filming, we actually had to [shoot] the photographs that she bribes me with," he recalled.

What an iconic film. (Warner Bros.)
What an iconic film. (Warner Bros.)

"That was like, 'Hi, how are you. Alright, pardon me, I'm going to take all of my clothes off.' I never felt pastier and doughier and just less attractive,"

Both Aniston and Day previously said they’d be up for revisiting Horrible Bosses.

He told The Hollywood Reporter last year that he’d ‘had some conversations about it with some people involved in front and behind the camera’.

Day added: “We’ll see – hopefully there’s an appetite at the studio.”

And Aniston told People that it’s the project she’d be most interested in revisiting.

“Jason Bateman and I were talking about that, and Charlie Day has been talking about it a lot too,” she said. “So that’s something that we think would be super fun.”

Aniston added: “The characters are hilarious, and we need comedy. I personally think comedy is a necessity. That’s one that we would have a really fun time, I think, going back to, seeing where those crazy cats are today.”

Featured Image Credit: Warner bros

Topics: Jennifer Aniston, Film, TV and Film

Jess Battison
Jess Battison

Jess is a Senior Journalist with a love of all things pop culture. Her main interests include asking everyone in the office what they're having for tea, waiting for a new series of The Traitors and losing her voice at a Beyoncé concert. She graduated with a first in Journalism from City, University of London in 2021.

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@jessbattison_

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