An investigation of Jennifer Aniston’s mid-Friends movie career

We need to talk about Jennifer Aniston. No, not her upcoming Apple TV series opposite Reese Witherspoon; the level of secrecy surrounding that project will drive even the most stable person insane. And no, not her hair, or the fact that no amount of Aveeno use or SmartWater consumption will make even the slightest difference in our appearance. And no, not her divorce from Justin Theroux, because, duh!

We’re going to talk about her mid-Friends movie career. It’s a period that’s often overlooked due to both the massive popularity of the Greatest Sitcom of All Time (yes, we said it) and her appearances in more recent big-budget flicks. But today, on the 20th anniversary of The Object of My Affection, it’s time to pay tribute to that very specific era of the late ’90s that was so fruitful for the actress both on and off-screen.

Our story begins, of course, with Friends. It put Thursday night television on the map — and don’t let anyone tell you differently — and Jennifer Aniston was, of course, the breakout star of the show — again, don’t let anyone tell you differently. Right around the time that the entire country was requesting “The Rachel” haircut and breaking out their adult overalls, the actress was doubling down on her success by branching out into film.

Her first big-screen gig came with Picture Perfect, which also happened to be her first official foray into rom-com territory. She played opposite Jay Mohr — perhaps the most 1997 casting of all time — as Kate, a (what else?) young advertising executive who is (what else?) unlucky in love. After catching increasingly more heat from her mother about her single status — Kate was 28, in case anyone was wondering what it was like to be a woman in 1997 — she lies about being engaged in order to impress her boss. Naturally, complications arise.

It wasn’t the most creative of concepts, but for Friends fans it felt like being able to spend 90 minutes straight with a slightly more together Rachel Green, slip dresses and wispy bangs included. Watched from the slightly more woke perspective of 2018, Picture Perfect is also a pretty solid argument for the necessity of the women’s movement. Practically every single thing that happens to Aniston’s Kate is maddeningly sexist — she’s stuck in the boys club of the ’90s advertising industry, she gets passed up for a promotion because she’s not stable enough (!), her boss is constantly commenting on her wardrobe, and the only way for any of the men in her life to notice her is to pretend she’s engaged. #JusticeForKate.

The following spring brought The Object of My Affection, more solidly nostalgic rom-com fare. Aniston played Nina, a social worker who offers her extra bedroom to George, a first-grade teacher who quickly becomes her best friend. Everything is going great until Nina gets pregnant with her boyfriend and quickly realizes that she’s actually in love with George. To make matters even more complicated, George is gay. It’s kind of like My Best Friend’s Wedding meets I Love You, Man meets that one season of Friends when Rachel has Ross’ baby but also accepts a proposal from Joey.

The most important thing to know about The Object of My Affection is that it boasts one of the most impressive casts ever. To start, Paul Rudd stars opposite Aniston as George, marking the first of their onscreen collaborations. Allison Janney plays Nina’s stepsister and Alan Alda plays Janney’s husband (power couple!). Tim Daly and Steve Zahn round out their group of friends, and there are even cameos from a very young Sarah Hyland and Hayden Panettiere.

Completing Aniston’s late ’90s movie trio is, of course, Office Space. Sure, the narrative focused mostly on the incredibly disgruntled employees of Initech but it would have been nothing without Joanna and Chotchkie’s. The flick allowed Jen to show off her drier comedic chops and, most importantly, her flair. Here’s to your flair, Jen.