BIGGIE'S PLACE

HBO’s Entourage originally aired while I was in my mid-late 20’s, a perfect time for someone with big Hollywood dreams. This was appointment television for me. It drove me nuts that each episode was barely 25 minutes long, even though that was actually the perfect length for a cable comedy. Selfishly, I wanted more, especially from the episodes that featured our protagonist, Vincent Chase, being on a set or anytime Ari and/or Eric were interacting with big-name filmmakers. My primary goal with the show was to glean some, ANY insight into how the business really worked. And it frequently delivered.

It’s funny because the parts of the show dealing with relationships and the guys trying to get laid every day were the parts that interested me least. But that stuff never bothered me because even though I didn’t really care, they presented those situations in funny, unique ways that could only happen in Hollywood. I was watching to gain industry insider knowledge, but it was certainly fun to get some insight into the Hollywood lifestyle, and I was always interested in who the show would bring in for cameos from week to week.

My favorite cameos, both then and now, were those by high-profile directors and writers, such as James Cameron (who actually had a short arc over multiple episodes), Peter Jackson, Frank Darabont, Aaron Sorkin, Peter Berg, Nick Cassavetes, Brett Ratner, Paul Haggis, Gus Van Sant, Randall Wallace, a hilariously brief appearance by Stephen Gaghan, M. Night Shyamalan, Sydney Pollack, Penny Marshall, and Martin Scorsese (who was literally in one scene).

There were also cameos by some of my favorite people, including Tom Brady and Larry David. Series co-creator/executive producer Mark Wahlberg also appeared several times alongside his real-life friends that inspired these characters.

There were also several cameos by people who would later be “canceled” in one way or another from various #MeToo allegations, including Danny Masterson, Paul Haggis, Brett Ratner, Tom Sizemore, and Diddy. I suppose that was inevitable given how many cameos the show had in total, but one always wonders who knew what and when about these people while they were actively working in the business.

Then there’s the needle drops. No other show has introduced me to more music that I ended up loving. Every episode ended with a song over the end credits, and I frequently would feel the need to go and find/download those songs. The show had five music supervisors over the course its run, so kudos to all of them.

The best aspect of the show is that it’s character-centric. You know each character and come to anticipate how they’re gonna react to these wild circumstances. They stay consistent while maturing over time. Johnny Drama stumbles along, but continues to try and improve his own acting career to get out of his younger brother’s shadow while remaining proud of Vince at the same time. Turtle starts out satisfied to just be in Vince’s orbit living the good life, but eventually also wants more for himself, as anyone would. Eric is never comfortable fucking around and desperately wants that long-term relationship at all times. Ari is always fighting to climb the Hollywood power ladder but still makes Vince a priority even when he doesn’t have to. Through it all they each remain loyal to Vince and each other, which is why we like them.

I won’t go into the storyline of the entire series because it remains fairly consistent until the later seasons. We get a glimpse of what it’s like to be at the Sundance Film Festival, Cannes, various other industry events, and overall see how the studio system operated at the highest levels, none of which we’d really seen before on a weekly basis. What was it like for an actor who was in a major hit? What was it like for an actor after their movie bombed spectacularly? We see it all. I can imagine the show’s most dedicated viewers lived in Los Angeles, California and worked in the industry in one area or another. I lived in LA during the second half of season 3 (the only season to have 20 episodes), and we would have viewing parties those Sunday nights. It was fun to watch the show with like-minded people, even if for a brief time.

The show finally made a major swerve in seasons 6 and 7. Season 7 ends really strong with Vince having a drug & alcohol problem, and we see how his problem becomes the problem of everyone around him. I did find it odd that Sasha Grey, who plays herself as the porn star Vince is dating who gets him into drugs, would have played this character who embodies many of the worst stereotypes of people in the adult entertainment business. But I suppose a lot of those folks will take mainstream work like this however they can get it. Either way, this season saw the first real turmoil in the relationships between the guys, which resulted in some strong, dramatic character work.

What were the best performances on the show? That’s easy: Jeremy Piven & Kevin Dillon. Both of them had complete ownership over their characters. Piven won 3 Emmys for playing Ari Gold, all of them deserved. Dillon was nominated in the same category 3 times, and those were the only acting nominations the show ever got. In supporting roles, I always liked Debi Mazar playing Vince’s publicist, Shauna, and of course Rex Lee as Ari’s assistant, Lloyd. Today, the constant gay-bashing jokes thrown at him by Ari would never fly, nor would most of the workplace abuse Ari dished out on a regular basis. Some of that stuff really doesn’t work anymore, but a lot of it is still funny now, because funny is funny. Let’s face it, if Rex Lee had a big issue with the abuse his character took, he probably wouldn’t have participated in the show for that long, would he?

The show was nominated for Best Comedy Series at the Emmys 3 times, and at its best was a truly high-quality show from a writing standpoint. I ended up giving 7 episodes a 9 rating on IMDb. Probably the biggest long-term beneficiary behind the scenes was director Mark Mylod, who shot many of the show’s best episodes (23 in total) and has since gone on to direct for several other high-profile shows (including 16 episodes of Succession, 9 for Game of Thrones and 12 for Shameless) and made his feature debut with The Menu, a movie I absolutely love. He’s one of the best TV directors in the industry today (with 4 Emmys of his own, all for his work on Succession) and can shoot the shit of out of a movie with a good script. It’s a damn shame mainstream Hollywood doesn’t make the kind of movies anymore that would most benefit from his involvement. I digress…

If you’re wondering, easily the worst performance on the show by a regular character was the kid who played Ari’s son, who of course was played by showrunner Doug Ellin‘s real-life son, Lucas Ellin. It’s no surprise he’s done no other acting in the years since. It was clearly a nepotism, “go to work with dad” hire, and he was bad even by kid actor standards. I don’t wanna be mean to the kid, but he was so raw it took away from the scenes he was in where Jeremy Piven and Perrey Reeves playing Mrs. Gold were trying to do real acting as his parents.

There are some recurring tropes I didn’t much care for, most notably that any woman anywhere wants to fuck Vince the second they lay eyes on him. If the boys go to a restaurant, he fucks one of the waitresses that night. If they go to a fashion show, he fucks one of the models. If Vince does a late-night show like Jimmy Kimmel, he’s fucking the actress who also appears on the show that night. If they go to a goddamn martial arts studio, he’s fucking the woman doing the training (this actually happens in one episode). I know there are people who can do this if they chose to, but I have a hard time believing a lot of “hot” actors do, particularly now in the age of social media where they’d be recorded everywhere they went. But I admit that may be utterly naive. I don’t know. I haven’t lived a lifestyle where women are constantly throwing themselves at me. Life isn’t fair. Regardless, a key part of almost any scene in the show is finding out which girl in that environment will be in bed with Vince by the end of the episode. I’m not sure I believe even Leonardo DiCaprio in his prime was behaving like this, but again, that’s just speculation.

The final season (a shortened one at 8-episodes) was kind of a dud, sadly. Of course the episodes were good enough to keep a fan into it, but there was hardly any real story progression or serious character development taking place. Most of the series’ best dramatic conflict hinged around the group desperately trying to make moves to keep Vince on the A-list. Most of the episodes in the early seasons end abruptly with the group receiving some form of bad news that carries into the next episode. That’s good writing. In the final season, his career woes are over, he’s got several offers at any given time, and isn’t struggling at all for money. It kind of removes a lot of the central tension that kept the series moving. In particular, the setup for the series finale is a disaster. Vince is chasing a smart, beautiful journalist who doesn’t date celebrities and clearly wants to be professional (played by the mesmerizing Alice Eve), but after several attempts at wooing her, she’s convinced to finally go on a date with him, and we don’t see this pivotal scene where he turns her. We just cut to the finale where she’s had a one-night stand with him and is ready for a quickie marriage in Paris, completely destroying her character. This is the best plot device they could come up with for a series finale?

The finale is well done. I just don’t believe it. They obviously mapped out where they wanted the main characters to be as the show ended, but how some of them got there left a lot to be desired. Reminds me of another famous HBO show that went 8 seasons. Then the show ended and I was sad because there was nothing similar to replace it.

A Major Motion Picture

When it was announced there’d be an Entourage movie, my first reaction was to wonder why? Of all the TV shows that can translate to the big screen, this was not high on my list of possibilities. For fans of the show, we’d gladly see it just to be back in that world for a couple of hours, but there seemed to be little chance of it reaching a broader audience or mattering at all to anyone outside of Hollywood or those who were big fans of the show. This was borne out at the box office, where it grossed just $49 million worldwide off a reported $39 million budget, a misfire by any standard.

I watched the movie the day after I finished rewatching the show, I think for the first time since it came out in 2015. In real life, there were nearly four years between the series finale in September 2011 and the film’s release in June ’15. Just long enough for most people to have moved on. For a show like this, you’d need the movie to come out within a year of the show ending for it to be culturally relevant (as if it were the premiere of a new season), and they badly misjudged how many people were still interested by the time the movie released.

The movie itself is fine. It’s a 7/10. Not bad, not great, and not necessary. It’s a bigger budget version of the show. It’s exactly what you’d expect, which is part of the problem. It centers around Vince making his directorial debut on a very expensive movie. Haley Joel Osment made a nice little comeback as the primary antagonist, the son of a rich Texas financier (Billy Bob Thornton) who gets put in charge of making sure his daddy’s money is being spent wisely, which of course leads to a host of “creative differences” that drive the plot. It’s not a terrible idea, but they could’ve made this a season-long story and probably gotten more out of it that way. Hindsight is fun.

Where Are They Now?

With nearly a decade of hindsight, you can easily make the case that Jerry “Turtle” Ferrara has had the best acting career post-Entourage. He’s worked the most consistently in projects people have actually seen, and been in some major movies. Adrian Grenier never became Vincent Chase and never seemed to want to (he’s mostly been reduced to direct-to-video movies), Kevin Connelly was never anything more than a sidekick, and Kevin Dillon’s career mimics Johnny Drama’s struggles so closely that you have to laugh about it. The biggest success story during the show’s run, Jeremy Piven, has been quietly shunned by Hollywood after having his own #MeToo issues that never really went anywhere. Even the show’s creator, Doug Ellin, has done virtually nothing since the movie in 2015. I do wonder why that is. HBO is a very loyal company. Almost anyone who creates a hit show for them gets another show made there, and he never did.

From the Entourage crew’s perspective, as I detailed earlier, director Mark Mylod easily wins that contest. He’s about to direct several episodes of the Harry Potter reboot HBO is doing for TV, which is going to be huge.

Could This Show Exist Today?

This is tough to answer, and that’s because celebrity itself is an entirely different animal in 2025 then it was 20 years ago. Young people now in the age range that watched Entourage back then don’t really look up to famous actors anymore. Instead, they worship the people they follow and subscribe to every day on YouTube, Instagram or TikTok. I’ve made it clear in the past what I think of that kind of fame, but there’s no changing it. In order to do Entourage now, it would have to be about some big social media celebrity and the people who live in a big rented mansion with them, and that’s not something I’m interested in at all. You’d be following what these people do to stay relevant, how they use modern tech from day-to-day, how they compete for corporate sponsors, the trouble they might get in for livestreaming some of their hijinks, and all that shit. No, thanks.

One of the things I liked best about Entourage rewatching it now is that the characters weren’t on smartphones all day and social media barely existed (there’s literally one reference to early Facebook in one episode). The world was better and more interesting without it. It’s not a coincidence that most of our best filmmakers choose stories not set in modern times…because they don’t want to deal with or even acknowledge all this shit. But I’m on a tangent again. I’m pleased to say that, for the most part, Entourage holds up really well, so long as you aren’t cursed with the modern mindset that nothing is funny if the joke comes at someone else’s expense.