With ‘Entourage’ arriving soon, we examine classic films about boys being boys

A few nights ago, Warner Bros. hosted a very canny event that our own Louis Virtel attended at the Playboy Mansion, a screening of “Entourage” that may have felt like virtual reality for those who attended. While I doubt being surrounded by scantily clad bunnies influenced Louis one way or another on the film, it's likely you'll see a number of reviews that are perhaps more enthusiastic than they would otherwise be, and it'd be hard to blame anyone who fell for it.

One of the reasons the setting seemed so right for that particular film is because much of the charge of “Entourage” is watching the core ensemble swagger their way through Hollywood, doing whatever they want and rarely if ever facing any consequences as a result. It's always presented with a wink and a smile, just a case of boys being boys. We live in a world right now where that doesn't really mean what it used to, and I wonder how much longer this sort of movie is viable.

Warner Bros. certainly has a vested interest in getting this right. Look at how much money they made around the world with the “Hangover” series, which is pretty much the perfect big-studio of one of these films. The entire promise of that series is “these guys got so ruined that they don't even remember the night they had, and they have to put it back together.” It's an irresistible premise, and it's amazing how much mileage they got out of it. I'm sure they would love to see “Entourage” turn into a film franchise, and if this first one performs the way the first “Sex and the City” film did, then they may well get their wish.

In the meantime, if you're interested in seeing more films in the same vein, then we've got some suggestions for you, some of which are fairly similar to “Entourage,” some of which might stretch the general idea, but all of which depend on ensemble casts and that one basic idea: left to their own devices, boys will be boys.

“Very Bad Things” (1998)

Peter Berg has managed to build a fairly respectable career as a filmmaker, but his kickoff to his directing career is about as far from respectable as possible, and by design. The film jumps off from the “joke” that is so often made about killing hookers, something that should probably be explored at some point. There is some seriously dark pathology at work in any society where people can routinely joke about that particular thing because of the value we place on the lives of sex workers. The reason “Very Bad Things” works as well as it does is because it doesn't try to downplay how horrible all of these people are, and it doesn't try to redeem them. Instead, Jon Favreau, Leland Orser, Christian Slater, Jeremy Piven, Daniel Stern, and Cameron Diaz are all taken on a guided tour of Hell by their own making. They earn every terrible thing that happens to any of them, and it serves as a nice refutation of the basic idea that boys behaving badly is a good thing or excusable as a simple part of human nature.

“Swingers” (1996)

Two years before “Very Bad Things,” Favreau wrote and starred in a movie that helped define young male swagger for at least a decade afterwards, making stars of both Vince Vaughn and Faveau in the process. What made “Swingers” so canny was the way the film put real value on the bond between young men and the also deflates the empty bluster of Vaughn's character. It is a movie that respects the importance of having your group of friends and the danger of buying into conventional roles blindly. It's an inviting world that Doug Liman paints with this one, and even today, its place in pop culture remains prominent. Just say “Vegas, baby, Vegas” to a room full of dudes and watch the reaction. It's downright Pavlovian. Or Favreauvian, as the case may be.

“Super Troopers” (2001)

Here's how you know you've made a lasting impact with one of these movies. If any phrase or action from your film becomes commonly quoted by guys, then you've done it both right and wrong. I'm aways amazed by how things get recontextualized as they enter the lexicon, and some of the worst behavior of these boys being boys becomes downright celebrated over time. One of the reasons I like “Super Troopers” so much is because even though the lead characters in this comedy have a healthy disregard for authority, there is a playful silliness to most of it that keeps even the most potentially distasteful thing seem downright charming. Whether they're having a maple syrup chugging contest or playing the “meow” game or offering stranded motorists mustache rides, there's something downright joyous about this misbehavior.

“A Hard Day's Night” (1964)

Richard Lester brought a great rowdy energy to this film, but the undeniable appeal of it is simply watching The Beatles at the absolute height of their fame goof around and play and be silly. It's a reminder of just how young they were, and it was also an unusual response to the sort of instant iconography that they encountered. They could have steered into celebrity and made themselves unknowable and removed from the public, protected, but they went the other direction. “A Hard Day's Night” made them seem human and accessible and audiences felt a connection to them that, real or not, made the Beatles into so much more than just a band for an entire generation or two or four.

“National Lampoon's Animal House” (1978)

Delta House may be disgusting and crazy, but they are loyal, and they take care of one another. Part of what I found so appealing about the boys of Delta House the first time I saw the film was the sense that they had each other's backs, and whatever bad ideas one of them had, they would all do their best to realize those ideas and join in. There's something celebratory about that kind of friendship, and it's little wonder the somewhat dying Greek system came blazing back to life after this film was released. The movie made fraternity (the idea, not the organization) look fun, no small task.

“The Wild Bunch” (1959)

Boys will be boys, even if they're dangerous old cowboys in their 70s. The outlaws in “The Wild Bunch” have spent their lives living by their rules, refusing to bend to anyone else's will. It's the thing that defines them, and when the modern world threatens to take their version of the Old West from them, they react the only way they can, by burning it all to the goddamn ground. The last third of this movie is a long sustained howl of pain and anger, an existential line in the sand drawn in blood and tears, saying “This is who we are, and this is how we live, and you can kill us, but you can never change us.”

“Reservoir Dogs” (1992)

Quentin Tarantino burst onto the scene with his ferocious debut, and so much of the appeal of his entire filmography can be summed up in the first scene in his first film. As a group of professional thieves and killers sit around a table, killing time, their conversation reveals each of them and how they deal with the world. It's tremendous character writing, and an example of how clearly men reveal their natures when they are at their most relaxed. At the end of the scene, as the guys walk out in slow-motion in one of the most iconic shots of the '90s, they cut the exact figure that any group of guys walking together believe that they are presenting, coiled danger and calculating machismo incarnate.

“Fandango” (1985)

Five guys. A road trip. An uncertain future. That's all it took for Kevin Reynolds to make a powerful first impression with a movie about a group of friends struggling to make peace with the future they're fairly sure is going to crush them all. Told in the shadow of Vietnam, there's a great easy energy to the ensemble here, and this is where Reynolds first encountered Kevin Costner, who has been the source of great success and great distress throughout the course of his entire career as a filmmaker. While the film isn't great, what makes it work and what gives it lasting power is the easy chemistry Reynolds captured, and the very knowing insight into the way friendship can give you strength but also make you vulnerable in ways you wouldn't expect.

“Anchorman: The Legend Of Ron Burgundy” (2003)

The greatest secret to this film's success is the casting of the action news team working around Will Ferrell's Ron Burgundy. Steve Carrell, Paul Rudd, and David Koechner are all absolutely perfect for their roles, and their chemistry as a group explodes in one of the greatest moments of the film, the rumble they have with all the other news teams in San Diego. These guys feel like actual friends, and I think it's easy for people to see themselves and their friends in these guys. I just wish I didn't have the nagging feeling that I am every group's Brick Tamland.

“Deliverance” (1972)

John Boorman was fascinated with films about people who were tested by some extraordinary circumstance, and “Deliverance” may well be his masterpiece. Even if they hadn't run into a couple of unfortunately randy rednecks, this trip down the Cahulawassee River would have pushed Ed, Lewis, Bobby, and Drew to the breaking point. Jon Voight, Ned Beatty, and Ronny Cox are all great in the film, but as their alpha, Burt Reynolds practically melts the cameras. He is pure animal power in the film, and it's small wonder he became a huge movie star as a result.

“Bottle Rocket” (1995)

When I walked out of “Bottle Rocket” the first time, I was convinced that Owen Wilson would never top his performance as Dignan, who is practically a Bad Idea Generating Device. I look back at it now, and there's such a sunny sweetness to this film that it almost doesn't feel like the same Wes Anderson who's been making films since then. Dignan is the perfect embodiment of that friend we all have who is always coming up with terrible ideas, but who is able to explain them in a way that makes it all seem perfectly normal and reasonable.

“The Last Detail” (1973)

Hal Ashby and Robert Towne collaborated to spectacular effect on this film about two Navy men who are charged with delivering a young recruit to military prison. Before they do that, though, they decide they're going to give him one perfect night of manhood to remember. Jack Nicholson and Otis Young are awesome as Buddusky and Mulhall, the MPs, and as soon as they get a look at Meadows, played by Randy Quaid, it's clear that he needs the guidance of more experienced men. We learn our own individual definitions of manhood from the men in our lives, and when your guides are this profane and this caustic, it's a rough ride.

“Down By Law” (1986)

I'm not sure there is any stranger group of men on this list than the stars of “Down By Law,” Jim Jarmusch's crazy story of the bond that is formed between three men in a Louisiana prison. Roberto Benigni, Tom Waits, and John Lurie are the guys, and they each have such a radically different comic persona that it's sort of like getting whiplash listening to the conversations between them in this film. That's the charge of it, though, and despite seemingly originating on three different planets, eventually these guys find some common ground, and that recognition of the things that bind them is what makes this comedy work.

“The Hot Rock” (1972)

Donald Westlake's books should have generated way more movies than they did, but every now and then, someone got it exactly right and realized that his crime novels aren't about plot… they're all about behavior, and this Peter Yates film perfectly nails that. With a cast including Robert Redford, George Segal, Ron Liebman, Paul Sand, and Moses Gunn, this story of a whole bunch of thieves all chasing the same diamond is very wise in the way men measure themselves against one another, and the lengths that will drive them to.

“Ocean's 11” (2001)
“Ocean's 12” (2004)
“Ocean's 13” (2007)

The real appeal of this series isn't the heists, but rather the notion that you're getting a chance to hang out with this big fun group of movie stars, the same notion that drove the original film. In that case, the Rat Pack were already thought of as a celebrity group of friends, but here, that friendship was basically whipped up by Steven Soderbergh. People were willing to show up every few years to watch George Clooney, Brad Pitt, Matt Damon, Don Cheadle, Elliott Gould, and Bernie Mac hang out and plan some bad behavior. And, yes, in the case of this series, Julia Roberts is absolutely one of the guys, and that is part of the appeal. Watching how the films would shift to make room for new people in each movie was part of the fantasy, because anyone can imagine themselves becoming the new member of the group, joining them for the jokes, the good times, and the grand-scale larceny.

“Diner” (1982)

Finally, no list like this would be complete if it did not pay due respect to Barry Levinson's ode to a group of friends fighting as hard as they can to hold adulthood at bay. While it may have been set in 1959 Baltimore, “Diner” felt universal to me as soon as I saw it, and as I've gotten older, the film only seems more and more true, more and more accurate about the shifting sands of friendhood, especially when people are on the cusp of something as profound as the end of adolescence. I would urge people to seek out the far less well-known “Tin Men” by Levinson as a great portrait of the ugly side of male competition, but “Diner” will always be his gold-standard classic. Steve Guttenberg, Daniel Stern, Mickey Rourke, Kevin Bacon, Paul Reiser, and Tim Daly are all great in the film, and the friendship between them feels completely real. No matter what the year, no matter how things change in the fine details, the truths of “Diner” remain true, and Levinson's movie echoes through any group of guys you've seen since, arguing over inanity, exchanging insults as currency, and busting balls for the sheer sport of it.

“Entourage” arrives in theaters June 3, 2015.