Boy Movies #73

The Entourage issue

You’re reading Boy Movies, a newsletter about movies for boys. Today’s issue is about a TV show for boys that was eventually turned into a movie for no one.

Ohhhhh YEEEEEAAAAHHHH!!!

My first memory of the television show Entourage involves my mom informing me that “everyone” has made a cameo on Entourage. This was an incredibly glam statement to hear in my youth, coming from the most glam woman I knew. (That’s still true.) My mom watched every episode of this Mark Wahlberg-produced program during its original 2004 to 2011¹ run on HBO (Mom, please tell me if this isn’t true when you read this in two to five weeks) and so I trusted her on this. Before I started watching Entourage, it existed in my mind on a pedestal. I recognize this as an utterly deranged thing to say now, and yet I am saying it to you all in the interest of being fearlessly real.

In October 2010, a few days after my dad died, my mom and I drove to Best Buy. I don’t remember what brought us there; I think sometimes you’re just sad and you find yourself at Best Buy. It happens. I could not tell you what our intention was in going there, but the one thing I do remember is drifting over to the vast DVD section and zeroing in on the first season of Entourage, the impossibly chic TV show I’d heard so much about. I remember asking my mom to buy it for me (I was fifteen and jobless) and immediately popping the first disc in the DVD player the second we got home. I was at a place in my life where I couldn’t remember anything I used to enjoy and I badly needed something to occupy my time, and for whatever reason, I answered the siren call of those four guys from Queens, just trying to make it (and get laid — haha hell yeah, brother) in Hollywood. There’s a direct line that goes from me watching every episode of Entourage as a teenager to me starting Boy Movies as an adult.

Famously, I experienced a major depressive episode this summer (I’m doing better now) and, as I did during the first major depressive episode of my life, subsequently turned to Entourage, kicking off my first rewatch since the show ended. It’s hard to say what got me there, or why I found it so comforting on my many, many low days. Entourage purports to be a comedy, but the jokes are undetectable to modern ears. It is pure chauvinistic white noise, a series that follows a rich actor and his three friends who mooch off of him, none of whom have any problems aside from the fact that they sometimes can’t have sex with the girls they want to have sex with. (They usually end up having sex with her in the end, though.) They drift through Los Angeles with the kind of post-9/11 breeziness that reads like science fiction today. There’s such a strong sense of hedonism to those first six seasons, and it’s not until season 7 that the show even experiments with its first semblance of real conflict. (On Entourage, “real conflict” is Adrian Grenier’s perennial blank slate Vinnie Chase randomly developing a cocaine addiction and dating a porn star. It ends with him losing a fight to Eminem, playing himself, in the season finale.) By the eighth and final season, all that conflict has been scrubbed away. Good: We didn’t sign up for Entourage because we wanted to watch a complicated portrait of a troubled man!

Something funny happened with the timing of my rewatch, as 2024 marks 20 years since the premiere of Entourage, an anniversary that landed with nary a whimper. To put it in perspective, Entourage premiered in July 2004 and Lost premiered in September 2004. These shows overlapped for nearly their entire runs, with Entourage outlasting Lost by a year. While memories of Lost seemed inescapable, I have to wonder who among us was even aware that it was the Entourage anniversary. If you were, there’s a good chance it’s because you’re a member of my inner circle and I cursed you with the knowledge.

Hard as Doug Ellin (that’s the guy who created Entourage) tried, the show has no lasting relevance. It’s special to me because of where I was in my life when I watched it for the first time, but few remember it so fondly. A follow-up movie was released in 2015 for literally no discernible reason — eight seasons of no stakes means there are no loose ends to wrap up, so why bother? That remains a mystery to me, as I’m not sure who was begging for this movie aside from Mark Wahlberg, a man who wakes up at 2am to pray and work out. I saw the Entourage movie in theaters on opening weekend (hi to my friend of forever Mab, who sat and hooted right beside me) and never revisited it, though I’ve thought about the fact that it deploys an I Need My Girl by The National² needle drop in the final hour at least once a week in the almost ten years (?!) since. I started my Entourage rewatch on June 1 (happy Pride) and finished on September 8, and of course no Entourage rewatch is complete without a repeat viewing of the movie, which is essentially one arduously long episode of the show. (Which ranked fairly high on the Boy Movies 100 Best Boy Movies list, one of many accolades the film received. Jk.) Much like when I became the first person on the planet to watch Madame Web twice, I am similarly the first person to watch the Entourage movie twice. This makes me feel nothing. It simply is.

In honor of that nothingness, I will now rank the Entourage movie’s top 10 most baffling celebrity cameos.

10. Mike Tyson

This isn’t that shocking to longtime fans of the series, who are of course aware that Mike Tyson becomes a client of Ari’s (played by the wretched yet highly watchable Jeremy Piven) in season 7. It’s more that you’re rarely expecting to see Mike Tyson in movies in 2024 so when he pops up you’re kind of like, “Whoa, okay.” Anyway, remember The Hangover?

9. Judy Greer

Girl, who the hell put Judy Greer here? She is the only person on this list who plays a character rather than herself, specifically a nameless casting director who laughs hysterically at Johnny Drama when his masturbation tape gets leaked online. (I dare you to ask me what the Entourage movie is about.) I would confidently bet $500 that she has no memory of being in this.

8. Emily Ratajkowski

It is not out of the realm of possibility that a hot model with notable boobs would appear on Entourage — that’s basically every woman on Entourage who isn’t Debi Mazar. What’s shocking about EmRata’s role is that her prominence in the film suggests that the Entourage movie exists outside the constraints of our reality. Entourage the show ended in September 2011, and Entourage the movie picks up just nine days after the events of the series finale, though it was filmed in 2014 and released in 2015. Emily Ratajkowski plays herself, and is spoken about as if she is a prolific actress. At one point, she even asks Haley Joel Osment’s character if he’s seen any of her films. But Gone Girl, her first major acting role, wouldn’t be released until 2014, about three years after the events of the Entourage movie. Not even the 2013 music video for Robin Thicke’s Blurred Lines which catapulted her to infamy (and earned a spot on the Boy Movies 100 Best Boy Movies list…) had stormed the world stage yet. If we’re going by the timeline established in the opening moments of the film, this woman barely existed yet. Which begs the question: What dimension does the Entourage movie take place in?

7. Ronda Rousey

She dates Turtle, whose whole thing is that he’s skinny now.

6. Calvin Harris

In terms of realism, it actually makes sense for Calvin Harris to be in the Entourage movie, but we once again have a case of “I am simply never expecting to see Calvin Harris,” and so he comes at #6.

5. Tom Brady

Now this ranking is getting good.

4. Piers Morgan

Mhm.

3. Kelsey Grammer

Right.

2. Matt Lauer

Yeah.

1. Armie Hammer

Ding ding ding we have a winner. The fictionalized version of Armie Hammer as depicted in the Entourage movie is established to have dated the fictionalized version of Emily Ratajkowski, a detail that factors heavily into his single scene.

Honorable mention goes to Steve Mnuchin, who has a producing credit on this masterpiece. Memba ha?

The Entourage movie is currently available to stream on Netflix.

1. The series finale aired on 9/11 btw.

2. Allison lore: The National is my literal favorite band.