This July will mark the 15th anniversary of the premiere of Entourage, a moment after which the world would never be the same. Or it would. It definitely would. Although for those people who watched the show, at the very least, talking on the phone would forever be more entertaining.
I don’t know about you, but whenever I watched an episode of Entourage, I wanted to talk on the phone and make deals and strongly suggest someone fix it, whatever “it” might be.
I wanted to make plans and say things like “That sounds excellent” or “I would love to be a part of it” or shout out a string of numerous expletives I don’t feel comfortable sharing because who knows, maybe my mom is reading this.
I also wanted to both drive around with friends or be driven by someone while in the car with those friends. To this day I still think having a driver would be pretty sweet.
Entourage was pure fantasy for those who will never come close to the kind of life the show portrayed, hence the idea of it being “lifestyle porn.” It was a form of escapism, and for the most part, endlessly enjoyable.
The show got a little dark there as it rounded the back nine, which I found problematic (although, in hindsight, that wasn’t the only thing that was problematic about the show). I wasn’t interested in Vincent Chase struggling or coping with something. If I was down for him going to struggle with anything, it was him trying to convince James Cameron to let him be Aquaman.
I wanted my Entourage struggles to be as absurd as the show itself. When rifts started growing within the crew and substance abuse issues started emerging, that popped the balloon. A popped balloon is a useless balloon. Just ask a toddler.
Yet regardless of that late series shift in tone, Entourage has endured and is still a fun rewatch. One of the big reasons is that the show’s characters—mainly the main four dudes—have always seemed like a good hang.
However, let’s ask ourselves: which one would be the best one to be drinking buddies with? And for the hell of it, let’s throw some of the other series regulars in the mix.
Gary Busey is not included, but if he was, he’d be number one.
10. Scott Lavin
Lavin, played by Scott Caan, came along during the show’s sixth season, positioning himself as a foil and nemesis to Eric, as he was a rival when Eric signed on with a major agency. For the most part, Lavin was fine but let’s not forget this dude’s enabling of Vin sent both Vin, the dudes, and ultimately the show down a dark hole.
Not cool, Scott Lavin. Super not cool.
When it comes to drinking, I want nothing to do with heading down a dark and troubling hole. That sounds terrible. I want my holes to be…nope, never mind.
I don’t trust Scott Lavin and if I’m doing any kind of drinking, I would prefer to be in the company of someone I trust. I don’t feel like this is a big ask.
9. Vincent Chase
A fun fact about Entourage is that the show’s main character was also it’s worst. Crazy, I know. But it’s true.
Think about it. How many times did the show turn it’s attention to something ol’ Vinnie Chase was doing—especially on his own—and you found yourself getting bored? You might have forgotten because it’s been a while but I would bet you a Ducati motorcycle that it was at least a handful of times.
The pros if you’re out with Vinnie—and this is peak Vincent Chase we’re talking about, not spiraling and troubled Vincent Chase—is that you’d be able to get into any club you’d want, would have no problem getting a table at a restaurant, would be surrounded by ladies and hey, the drinks would probably be free. He’s a celebrity. On a basic level, going out partying with a celebrity sounds fantastic.
However, let’s not sleep on the cons.
You’d be able to get into any club he’d want because he’s definitely not going someplace you want to go and the same goes for a restaurant you’d have no problem getting a table at. I’d like a say in where we’re going to eat but that doesn’t seem like something Vin would want to hear.
He’d want to go where he’d want to eat and probably wouldn’t care too much if you don’t feel like eating sushi at the moment. The ladies you’d be surrounded by most certainly wouldn’t be interested in you and the drinks might be free, but there’s a damn good chance that they’d only be free for him and not you.
Oh, uh, just a PBR for me then.
You can’t get distracted by the shiny objects, kid. Vincent Chase is a shiny object.
8. Melissa Gold
Ari Gold’s wife was very nice, seemed like a delight to be around, and would probably be a pretty fun drunk. I don’t know about you but that sounds like a winner to me. An added bonus would be we could probably meet up with Bobby Flay at some point and he could whip up some killer burgers for late night.
I would also be super interested in learning more about what life is like on the set of a soap opera and back in the day. Before the events of the show happened, Melissa starred on The Young and the Restless. Perfect! Let’s have a couple vodka tonics and talk about that.
They do so many shows! How do people memorize lines? Do PAs just shout lines out all day and the stars repeat them? I have so many questions about soap operas that I didn’t even know I needed answers to. Fascinating stuff.
Let’s get into, Melissa Gold.
7. Ari Gold
Provided you could stay on Ari’s good side (which is pretty questionable) Ari would probably be great to hang out with. If you want stories, he’d have stories. If you want gossip, he’d have gossip.
Oh, I also can’t imagine how much fun it would be to be there when Ari loses it on someone! That would be awesome. There are few joys more pure in life than standing behind someone who is mercilessly going after someone and you can just sit back and enjoy it.
Here, watch this now legendary scene.
Now, watch it and imagine that instead of Ari being at his kid’s birthday party, he was out drinking with you. You’re listening to Ari tell stories about the time he got this actor to do this part despite this director’s objections when he gets that call from Eric. Now you get to roll with him as he storms the beaches and tears little Josh Weinstein apart. You get to hang back while he destroys that dude and you get to just enjoy the show. And what a fantastic show it is.
Then you get to get back in the car and have some more fun.
I’d say Ari should be higher on this list but remember how this started. Ari would be great to hang out with, provided you are able to stay on his good side. Ari flips moods like a skater flips boards at the X Games.
It’s risky, but the risk may be worth it.
6. Johnny Drama
Oh boy. What to do with this maniac?
Johnny Drama could either be the best drinking buddy or the worst. There is no in-between here. Johnny Drama doesn’t do in-betweens. Johnny Drama looks at a gray area and laughs at it. He is a man of polar opposites, of opposing sides in a conflict.
As far as being the best drinking buddy, we have to give credit where credit is due. Johnny Drama is a loyal effin’ dude. If he has your back, you know that he has your back.
Case in point: the Seth Green fight.
My dude came flying in without really even knowing what was going on, but sensing trouble, he immediately jumped in to back up his boys. I’m personally not the confrontational type and if I was in that situation, I’d be much more like Vin or Ari than Drama or Eric or Turtle.
I was in a fight once. It was in third grade. That’s all I remember. Life is about knowing your strengths. My strengths lie much more in giving moral support than engaging in physical altercations.
However, it’d be nice knowing that if things got heated while you were out with Drama, you had a god damn berserker on your side.
Of course, that leads us to Johnny Drama as the worst drinking buddy and it’s mainly because he’s a wildcard, and with any wildcard, there are inherent dangers involved. There are ups but there are also downs. If we’re going to appreciate the ups, e.g. the loyalty, then we need to appreciate the downs, e.g. the recklessness.
A night out with Johnny Drama might result in a lot of fun or it might result in you going to jail.
Again, there is no in between.
5. Lloyd Lee
Lloyd is loyal but with none of the baggage that comes with Johnny Drama’s brand of loyalty. He endured so much shit from Ari—SO MUCH SHIT—and kept on keeping on. Lloyd is a true warrior.
There might be more fireworks hanging out with Ari or Drama but sometimes you don’t want fireworks. Sometimes fireworks are a bit much. Lloyd is a safe alternative and there is absolutely nothing wrong with a safe alternative.
4. Sloan McQuewick
Sloan and Lloyd could be flip-flopped on this list, and truth be told, there really isn’t a solid reason why Sloan is ranked higher.
Well, there might be one reason.
Beyond that, though, Sloan was wonderful and as per personal policy, I like to try and make it a point to spend as much time as possible with wonderful people.
3. Billy Walsh
So, for the most part, characters are being ranked by how we generally remember them, not how they might have been when the series ended. For example, Ari is ranked as if it’s the Ari Gold we know and love, not the humbler version of Ari who was there when the series ended. Vince is ranked as Peak Vince, not the Vince who was on drugs or was being weird for whatever reason at various times throughout the final season. We’re going with the way we remember these characters overall, not how we remember them at the end.
With that being said, Billy Walsh is typically remembered as the ultimate loose cannon, the dude who went nuts while in Colombia shooting Medellin and had to fall off the radar for a couple years to get his head right. That Billy Walsh would be ranked much lower on this list.
Instead, I’m going with the Billy Walsh from later in the series, the version of Walsh who had mellowed out, becoming both a family man and an ordained minister. I’ve also become a family man and as a result, I enjoy the company of other family men (i.e. other dads with whom I can make jokes about not sleeping and endlessly watching Paw Patrol with.)
That version of Billy Walsh is someone I could see myself hanging out with.
Would the whole ordained minister thing possibly get in the way? Perhaps.
But it’s nothing a few shots of tequila can’t resolve.
2. Eric Murphy
First off, Eric would have to leave his phone at home. Or in the car. I don’t care. But either way, no phone dude.
He would be on it the entire time and then I’d be on mine the entire time and then for crying out loud, why are we even out? I could be scrolling through Instagram at home and drinking beers that are significantly cheaper instead of doing it at a bar. Plus we’d look like assholes sitting there, two grown men, just scrolling through our phones.
No phones Eric. No phones!
So we ditch the phones and the tug and pull of Vince’s needs (or Ari’s) and I think Eric would be a quality hang. We could talk sports, movies, and probably even some television. He’s a New York guy. I’m a Boston guy. That’s always a bit of fun.
Of everyone on this list, Eric seems like the safest bet to do some drinking with.
PROVIDED HE LEAVES HIS PHONE BEHIND.
Eric may very well be the safest bet, but Turtle is both safe and interesting. Turtle is like Eric but with more style. If they were ice cream, Eric would be vanilla, whereas Turtle would be some cool flavor like sea salt caramel latte. There’s nothing wrong with vanilla. Vanilla is fine. But given the choice, you’re not picking vanilla.
However, you’d need to keep the phone in the car too, Turtle. Vince can wait.
I want to hang out with Turtle because Turtle seems like a good dude, isn’t high maintenance, and is generally pretty chill. This list is essentially comprised of personal preferences and nowhere is that more evident than this pick of Turtle at number one.
I’ve known dudes like Turtle and have always enjoyed my time with them, whether it’s hanging out watching basketball together or just chilling and shooting the shit. Turtle seems like the kind of dude who could talk about anything and those kinds of people are prized commodities.
He—like Eric—would just really need to leave the phone in the car.