‘Entourage’ Deserves More Credit for Its Dynamic Female Characters

I recently decided to rewatch Entourage, when I needed something that was fun and comforting and wouldn’t require too much thinking. And fully aware that it’s 2019, I went into this rewatch completely understanding that this show might not hold up, might not pass our current PC standards, and certainly might not be #MeToo friendly. Today marks the 15th anniversary of Entourage’s premiere on HBO, and in that time, much has been critiqued about the show, especially when it comes to the female characters. But I was quite pleased to discover that really it was always the women who were in control on Entourage.

Sure, the comedy series focuses around five straight white men (the entourage plus Ari), but the female characters are much more complex than one might expect. They’re executives (at least three of the women on this show hold high-ranking entertainment industry positions, which feels like a higher number than women who actually filled those positions IRL at the time), they’re loyal wives and girlfriends that are in control of their relationships and sexuality, and overall they simply take no BS from the men around them.

Okay fine, that Perrey Reeves is credited as “Mrs. Ari” isn’t the most feminist move, but we later learn her real name is Melissa and she has got Ari (Jeremy Piven) by his balls every step of the way. She comes from money so she’s not with him for his, she lives her own fabulous life, and she punishes him when he flakes on date night or family obligations. This is a woman who can show up and smile as his plus one and later drag him to couples therapy. She’s not a pushover, she puts her foot down when it matters, and when she left him in the later seasons it was savage but necessary. Ultimately, Ari needed a match that was no-nonsense, honest, and challenging and she proved to be all of those things instead of just a nodding housewife (oh my god, what an amazing Real Housewives cast member this character would’ve been though).

The same goes for Emmanuelle Chriqui as Sloan, Eric’s (Kevin Connolly) on-off girlfriend, a woman who held her own job, despite coming from money, and was never one to hold her tongue. She was supportive and encouraging of E, who, let’s be honest, had to be a frustrating boyfriend at times. Sloan could be both thoughtful and sexy while still demanding what she deserved, and that’s only part of the reason she quickly became dream girl of so many viewers.

In fact, many of the girlfriends on this show called the shots when it came to their relationships with the guys. Jamie-Lynn Sigler initiated her relationship with Turtle (Jerry Ferrara) by giving him a handjob on a plane, and it turned into a sweet and supportive romance — and just one of MANY where the women were in a much different (read: better) league than their male partners. There was a respect and admiration for these women, along with a healthy dose of disbelief that they would ever want to be linked to one of the guys. The Mandy Moore-Vince relationship was enthralling, and not the only time the mega-famous Vince (Adrian Grenier) was portrayed as a less than smooth Lothario. From his flirtation with the famously virginal Justine (Leighton Meester) to his relationship with Sasha Grey, Entourage may have even been sex-positive before that was a term we knew existed.

This also applies to studio executives Dana Gordon (Constance Zimmer) and Amanda Daniels (Carla Gugino): they knew how to make deals in boardrooms and bedrooms. It would be easy to limit them to simply “sex things” but this show actually gave them so much more to do. They were in charge of the production of films, the deals made behind the scenes, and the reason Ari frequently found his blood pressure rising. Talk about a genius move to make them frenemies of the power agent. It was sweet when they worked together, and even sweeter when he (and it was always him) that burned a bridge, usually by metaphorically setting himself on fire. It was Ari who recommended Dana as a studio head — yes, so that Amanda didn’t get the job. But that a woman, hell, TWO women were even being considered for a high-ranking position is quite progressive of the time.

And those weren’t the only women excelling at their jobs and even better at putting Ari in his place. The co-head of his own company Barbara (Beverly D’Angelo) was never afraid of giving him the shit he deserved, as was publicist Shauna (Debi Mazar) whose sailor mouth never allowed her to sugarcoat a single thing she said. These aren’t people-pleasers. They’re businesswomen. The same goes for Autumn Reeser’s Lizzie Grant, an up-and-coming agent who unwisely begins (and ends) an affair with Andrew (Gary Cole), but very intelligently argues her value to the company. She’s not just competent — she’s damn good at her job.

A quick glance at Entourage will provide you with plenty of shots of unnamed models strutting around a pool with limited clothing on, yes. But these women were also owning their sexuality, sleeping with members of the entourage when they wanted to — and passing on several opportunities as well. And it wasn’t just the young ladies using sex to their advantage, it was women of all ages, including infamously, Melinda Clarke with Eric. In fact, Entourage employed more women over 30, hell, over 40 than you’d probably even realized.

This is not to say Entourage and its characters, specifically Ari, were respectful of women at every turn. The character of Ari was designed to be crass and provocative and in all honesty, his rude remarks directed at women were nothing compared to the homophobic and terrible words spewed in his assistant, Lloyd’s (Rex Lee) direction. But we as an audience were supposed to recognize Ari as a monster and appreciate the women for rarely stooping to his level.

If it’s been a few years since you’ve revisited the HBO comedy series, I encourage you to do so. You might be surprised exactly how meta and insightful and ahead of its time the show proves to be. But for sure, watching these dynamic female characters (and portrayed by such a great crop of actresses) in leadership roles has been the most pleasant surprise of Entourage. They pushed back on the men, stood up to them, and yes, when they wanted to, even straddled them. They’re powerful decision-makers in their personal and professional lives, and they consistently prove to have bigger balls than many of the male characters they dealt with on a regular basis. Let’s hug it out, boss bitches.

Where to stream Entourage