Inside Ben Stiller and Jennifer Aniston’s relationship

When you think of Jennifer Aniston’s close circle of friends, actor Ben Stiller probably isn’t the first name that comes to mind. However, the two stars have actually been good pals for more than decades now. They first worked together on a memorable episode of Aniston’s fan-favorite series Friends back in the late ’90s before teaming on the big screen in the 2004 hit Along Came Polly. Stiller even introduced Aniston to her ex-husband, Justin Theroux, who he’s also known for years. (More on that later.)

Although both Aniston and Stiller have had a lot of co-stars over the years, they’ve hit it off to the point where their relationship has blossomed off screen as well. We just hope that Adam Sandler, another funny friend of Aniston’s, doesn’t get too jealous. But considering that Aniston’s Murder Mystery co-star is also friends with Stiller, we’d imagine he just goes with it! Let’s take a look at Aniston and Stiller’s friendship over the years. 

Jennifer Aniston and Ben Stiller had a bad TV date

Ben Stiller guest-starred on the third season of Friends in 1997, playing a man with severe anger issues in an episode titled “The One With The Screamer.” In the episode, Jennifer Aniston’s character Rachel is newly dating Stiller’s character, but she doesn’t witness his angry outbursts until the end of the show when he flips out on a pet chick for peeing in his hand.

Many consider Stiller’s appearance on the classic sitcom to be one of the funniest celebrity cameos of the entire series. Refinery29 put Stiller on a list of the most memorable Friends guest stars. We’d have to agree. The relationship between their characters ends poorly (Stiller’s character dumps Rachel after she catches him berating the pet chick), but they still had enough chemistry that Hollywood executives were eager to cast them together in a big-screen romantic comedy. That movie was Along Came Polly

Along came a Ben Stiller/Jennifer Aniston movie

Ben Stiller and Jennifer Aniston co-starred as a mismatched couple in the 2004 rom-com Along Came Polly. In the movie, Stiller plays an uptight and neurotic guy who runs into his free-spirited ex-classmate, played by Aniston, and she helps break him out of his shell. The movie was a big hit at the box office, earning $178 million worldwide, per Box Office Mojo.

Stiller and Aniston spoke about their on-screen chemistry in an interview with IGN while promoting the film. When asked how two actors get chemistry in a romantic comedy, Aniston said, “I don’t think you get that. I think that just has to be there.” Stiller agreed, adding, “I know that at the end of the day you hope that there is something there that works so it is fun to watch them together and you believe them as two people who would be in a couple or be attracted to each other or are just fun to watch together.” 

Aniston also admitted that their love scene in the movie, played up for comedic effect, was “awkward” and “nerve-wracking.” She added, “There is nothing sexy. But we had fun. We were really proud of ourselves at the end of that day that we made it through somewhat.” Stiller noted, “It’s just a weird experience. I think in this scene in particular, it is a comedic scene, so it makes it easier.” 

Ben Stiller introduced Jennifer Aniston to Justin Theroux

Jennifer Aniston and Justin Theroux first met, thanks to their mutual pal Ben Stiller. According to Us Weekly, the Zoolander star introduced the two in 2007 while Aniston was visiting the set of Tropic Thunder, which Theroux co-wrote. Despite the introduction, Aniston and Theroux didn’t start dating until they reconnected on the set of 2012’s Wanderlust, in which they co-starred.

Both remained close with Stiller, and Aniston and Theroux honored their pal at the 26th American Cinematheque Award Gala in 2012. Aniston made sure to get in a few zingers while honoring Stiller from the stage. Before presenting a video montage of Stiller’s on-screen romances, she joked, “Ben makes sexy smart — I mean smart sexy. His package is surprisingly large. Very expansive, and its lasting power speaks for itself.”

Aniston’s funny speech was one of the highlights of the night and a great example of how the two have supported each other over the years. As for Aniston and Theroux, the pair split in 2018, but maintained “deep respect and love” between them.

Ben Stiller adores his funny friend Jennifer Aniston

Ben Stiller has had plenty of kind words to say about Jennifer Aniston. As reported by Us Weekly, the actor once spoke about why he loves working with his longtime friend and collaborator. “There’s so few — I don’t know, how [to] say it. I don’t want to sound like, ‘Oh there’s so few women who are good at comedy.’ It sounds like a really sexist thing to say. But she really is one of the few actresses I’ve known who has such impeccable timing as a comedian and actress,” he told reporters while promoting Along Came Polly. “She really listens and she has timing… I don’t think it comes out of a premeditated sort of thing, it’s just in her bones.”

Stiller and Aniston have remained pals in real life, despite not having worked together again since Along Came Polly. Perhaps they just haven’t found the right project, but we’re still holding out for Along Came Polly 2. Regardless, it’s clear the two think the world of one another.

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