Way before Sydney Sweeney and Glen Powell’s on-screen magic had people scratching their heads about why they were not a couple, Jennifer Aniston and Jason Sudeikis were already in the crosshairs of Hollywood dating detectives. Despite their relationship remaining strictly platonic, ongoing speculation gained traction from their silver-screen sparks. Throw in any random topic, and Jennifer Aniston and Jason Sudeikis kick off a comedic banter as if reciting lines from a classic and wholesome sitcom.

Aniston and Sudeikis’ synergy shone brilliantly in the cinematic gems that make up this collection of the best movies featuring the two.

The Bounty Hunter (2010)

The Bounty Hunter, a 2010 action romantic comedy directed by Andy Tennant, featured Jennifer Aniston as a divorced journalist on a chase and Gerard Butler as her ex-husband turned bounty hunter pursuing her. This marked the first on-screen pairing of Jennifer Aniston and Jason Sudeikis, with the latter playing Aniston’s co-worker, who secretly had feelings for her. Despite critics giving it the cold shoulder and landing it nods for Hollywood’s worst, the film laughed all the way to the bank. 

The movie grossed $136.3 million against a production budget of $40-45 million. At that time, many fans could not help but wonder how Jennifer Aniston’s character could resist the charm of Jason Sudeikis’ character, echoing a sentiment that seemed to spill into real life. Nevertheless, little did anyone know back then that this pairing would later become a smash hit in Hollywood.

Mother’s Day (2016)

Mother’s Day assembled an all-star cast, featuring luminaries such as Kate Hudson, Sarah Chalke, Julia Roberts, Jennifer Aniston, and Jason Sudeikis, with a special cameo by Jennifer Garner. The holiday-centric film delved into the meaning of Mother’s Day for women in different situations and life stages. Aniston took on the role of a single mom adjusting to her ex-husband’s new, younger wife, while Sudeikis played a single dad navigating life with two daughters. 

This film marked the fifth time Aniston and Sudeikis collaborated on screen. One of the most interesting aspects of the movie was the awkward flirtation between Jennifer Aniston’s character and Jason Sudeikis’ character. Their on-screen chemistry brought a delightful energy and left viewers hoping for a romantic connection. 

Horrible Bosses 1 and 2 (2011 and 2023)

Boasting an all-star comedy lineup including Kevin Spacey, Jason Sudeikis, Jennifer Aniston, and Jason Bateman, Horrible Bosses was a comedy gem that demanded attention. The storyline revolves around three pals- Bateman, Charlie Day, and Sudeikis- who plan to eliminate their oppressive bosses, portrayed by Spacey, Aniston, and Colin Farrell. While the movie may be a bit rough around the edges and lacking originality, the clever cast turned it into a winner, capitalizing on a strong premise.

In Horrible Bosses, Aniston took on the role of Dr. Julia Harris, a boss known for her overtly sexual advances. On the other hand, Sudeikis played an account manager dealing with a new, drug-addicted boss after the demise of his beloved former boss. Despite the movie’s high entertainment value, the plot did not center on uniting Aniston and Sudeikis’s characters or her well-known pairing with Jason Bateman on screen, as her character primarily revolved around Charlie Day’s character.

The magic of Jennifer Aniston and Jason Sudeikis’s incredible chemistry truly came to life in their third project together. 

We’re the Millers (2013)

Even eight years later, We’re the Millers remains a timeless watch. Social media has immortalized its most quotable lines and meme-worthy moments, with “Wait, you guys are getting paid?” standing out as an all-time favorite. The storyline followed a small-time pot dealer who recruited his neighbors to pose as his family for a daring drug-smuggling operation from Mexico to the United States. Jason Sudeikis took on the role of David Clark, the mastermind behind the Millers.

Meanwhile, Aniston portrayed Rose O’Reilly/Sarah, a stripper hired to play his wife and the mother of his faux family. As the mismatched mom and dad in the movie, Jason Sudeikis and Jennifer Aniston brought a lot of improvised wit to their verbal sparring. The creators disclosed that the real challenge was keeping a straight face during takes. Sudeikis and Aniston, being genuine friends in real life, naturally translated into their on-screen chemistry in the flick.

Which on-screen pairing of Jennifer Aniston and Jason Sudeikis is your favorite? Let us know your thoughts in the comments below!