Entourage is the type of movie in which a line such as “I may have to jerk it before we even get there!” is almost guaranteed to be foreshadowing. Those words—the first in the film—are spoken by the bit actor Johnny Drama (Kevin Dillon) as he perches alongside his friends Eric (Kevin Connolly) and Turtle (Jerry Ferrara) aboard a boat in the territorial waters off Ibiza, Spain. They are speeding toward a luxury yacht on which the movie star Vincent Chase (Adrian Grenier) is partying with scores of bikini-clad girls. Drama is Vince’s half-brother/gofer; Eric (“E”) his best friend from the old neighborhood, now his manager; and Turtle his onetime driver, currently a Tequila mogul. The exact professional roles these characters fill, however—and the particularities of the crises and triumphs they’ve experienced over the course of the eight seasons Entourage aired as a half-hour-long series on HBO—could not matter any less. The only thing that counts, the movie seems to imply, is moments such as this one, an eternal present in which the boys can share a pair of oversize binoculars, sporting simultaneous boners—literal, metaphorical, and/or both—for the svelte, tan girls dancing on the yacht, the sort of girls American Psycho’s Patrick Bateman might have referred to as “hardbodies.”

The kind of bacchanalian spring breakish scene with which Entourage, the movie, opens was endemic to Entourage, the series, when it began airing in the impetuous pre-recession days of 2004. The popular imagination in the mid-aughts, as the aging among us will remember, was enthralled not just with an entity called “Young Hollywood”—a term that at that time included traditional entertainers as well as newly self-branding, reality-TV-famous rich kids such as Paris Hilton and the girls on MTV’s The Hills—but also with its close corollary, the apparatus of increasingly-Internet-driven gossip journalism.

It was an era of vulgar, cheerfully exaggerated gender roles, in which the perennially thong-flashing Britney Spears and her backup dancer Kevin Federline’s ill-fated nuptials (celebrated in September 2004, just two months after Entourage’s debut) featured bridesmaids and groomsmen wearing Juicy Couture tracksuits whose backs were emblazoned, respectively, with “maids” and “pimps.” Spears’s mental breakdown was a still-unimaginable three years off, the financial market’s collapse four. Yes, there were a couple of wars, but they were far away. Life was good.

Entourage reassured viewers that they, too, could be part of this dolce vita bubble. The joshing, loose tone of its fictional universe, in which young It-boy Vince brings over his “boys” from Queens to share in his newfound Hollywood fortunes, positioned its characters somewhere between the Rat Pack and the Pussy Posse—not as iconic as the former, certainly, but also not as gross as the latter—and contained just enough tongue-in-cheek to make the show palatable to critics. Vince’s agent, Ari Gold (Jeremy Piven), a rageful Jewish Napoleon forever on the brink of an operatic, wheeling-and-dealing-induced meltdown, was many viewers’ special favorite. One of his catchphrases, “Let’s hug it out, bitch,” became popular not just with lascivious finance bros but also among bespectacled, $13,000-a-year-stipend-receiving Victorian literature female grad students. (Alas, as I was at the time.) Everyone, it seemed, could be invited to the party.

As the years passed, however, Entourage became harder to stomach, and its inclusiveness less convincing. This was partly the fault of context. Post 2008, life turned more difficult for a lot of people, and the happy-go-lucky, Teflon quality of the show’s protagonists, with their effortlessly achieved Maseratis and mansions, began to grate. The “bros before hos” ethos fell out of general vogue, as did the notion that a group of horny white men fucking their way through Hollywood could count as an arrangement in which we’d all end up the victors, no matter our gender, race, or sexual orientation.

This is a lesson that some of the most successful recent navigators of popular culture, too, have grasped. Nowadays, our male celebrities can still have a bro squad in tow, but the carousing has to come with a twist, which is why Drake, for example—the half black, half Jewish rap superstar from Toronto, whose famously hangdog quality complicates an otherwise swaggery persona—is a genius worthy of his moment. Entourage, however, continued virtually unchanged. Years into its run, we could find the boys still metaphorically strutting around The Grove mall in Los Angeles, a somewhat worse-for-wear Horatio Alger with a Yankees cap, Ed Hardy shirt, and Seven for All Mankind jeans. By its 2011 finale, however, everyone seemed to understand that it was time to pack it up and move on. Vince was off to Paris to wed a British journalist; Eric was planning a move to New York to follow his pregnant on again/off again girlfriend Sloan; and Ari had left the agency he built to move to Florence and save his marriage to “Mrs. Ari.” As the credits rolled, Led Zeppelin’s “Going to California” played, and the song’s mournful lilt suggested the truth of the matter: The Golden State wasn’t being approached, it was being abandoned, the dream of a bro utopia deferred.  

But here we are in 2015, and we’re back on a yacht. What’s more, in the Entourage timeline, a mere six days have passed since the culminating events of the series took place. Vince’s quickie marriage didn’t work out (“I just separated from my wife. Give me a few hours,” he tells one of the bikini hotties on the boat); E hasn’t yet made it up with Sloan; Ari has reneged on his word to his wife, having been lured back to Hollywood with the promise of running a major studio; and Drama and Turtle are, as usual, up for anything.

The mildly animating conflict of the movie presents itself in Vince’s desire not just to star in Ari’s first movie as studio head, but also to direct it. Is he up to the challenge? And more importantly, will his boys rally around him to overcome the many obstacles that’ll arise along the way? That these questions require no answer is a given. What is more important, from an Entourage-centric narrative perspective, is that the plot begins with the guys still fully open to the possibilities derived from sex and money, the show’s evergreen catalyzers. The problem is that, as Drake has by now taught us, nothing was (or could, or should be) the same. What we’re seeing in the movie—and this is about as contemporary as it gets—is a portrait of men in crisis. While it’s true that Johnny Drama has always been the butt of Entourage’s jokes, his oversize bravado rendering him the fool—all the better to highlight the more staid, but still alpha, manliness of Vince and E—this time around the handsome but anodyne Vince barely registers, while the rest of the main male characters are, to a greater or lesser extent, messes, and not very smart ones at that.

Drama ends up the victim of a revenge porn plot after an ill-fated encounter with a sexting partner; a video of him masturbating is leaked and shared on TMZ as millions jeer. (A penis that is yearning to be jerked in the first act will, God willing, ejaculate by the third.) E is flailing, his attempt to get over Sloan by having random sex with starlets ending with the girls banding together to get back at him for his profligacy. Turtle is dating the MMA champ Ronda Rousey, playing herself, who challenges him to a fight and easily bests him, crushing his comparatively tiny head between her impressive thighs. There is also a new player, Travis, a horrible, dumpy Texas rich kid (the rather good Haley Joel Osment) whose billionaire father (Billy Bob Thornton) is financing Vince’s movie. Travis puts a spoke in the wheel of the production for a while, his sexual insecurity getting the better of him after the alluring Emily Ratajkowski (she, too, plays herself) chooses Vince over him. Ari, now running the show at the studio, listens hysterically to motivational “you are the master of the universe”-type affirmations in his car.

All of this isn’t to say that Entourage is subversive by any stretch of the imagination. There are still big bucks involved, almost all of them held in the hands of men, a lot of super-straight sex, and a lot of worked-out-to-within-an-inch-of-their-lives nude female physiques. The women are, for the most part, still hot young things—placeholders in triangulation plots—or, more rarely but no more expansively, studio hardasses and ball-busting wives.

And yet, after all this is said and done, it should be acknowledged there is some enjoyment in the movie. First, it’s appropriate for a film so obsessed with one of its character’s masturbation practices (Drama, in case you’re curious) that watching it recalls, to some extent, the viewing of porn. If you turn off your brain and put your ethics on hold, you can while a way a not unpleasant stretch of time, after which you might feel only slightly dirty. Who doesn’t like watching hot girls and big houses and shiny cars? After all, most of us have been trained from birth, to a greater or lesser extent, to adopt the acquisitive male gaze as our own.

But there is also something else. A few months ago, TMZ published pictures of Leonardo DiCaprio on New Year’s Day on a beach in St. Barts, partying with a score of much-younger-than-himself bikini-wearing women. A bit chubby, sporting a beard, his signature manbun, and smoking a vape pen, Leo was declared, as per TMZ’s gleeful slideshow headline, “King of the World!” DiCaprio is no has-been, and is still considered to be at the very top of his game as an actor. But what was igniting most of the readerly enjoyment here was the situation’s ridiculous over-the-topness. This very rich, very successful, palpably older man was, we could see, a major stud, sure. Just look at those young, beautiful girls, three or four to each arm! But also: What an idiot! What dim consciousness of mortality stamped out by delicious un-self-awareness! Entourage is similarly positioned, hovering worriedly over the cul-de-sac of masculinity on the verge of collapse. It’s almost enough to make you want to quote Plath: “Daddy, I have had to kill you. You died before I had time.”