With Entourage done and dusted after almost eight years on our screens, a quick internet search will let anyone know that there are more than a few differences of opinion about the show. Some people loved how it began, others how it ended. The middle worked well for for a majority and others loathed the entire show from its inception. Nevertheless, Entourage definitely has a legacy. I obviously watched the show and have seen every episode (many on more than one occasion), and whilst it comes nowhere near the top of any ranked list of shows that I’ve seen in my life, I’d be hard pressed to say that I didn’t enjoy almost all of it. The extent to which I enjoyed it definitely varies however, and while those who have seen it will have their own opinions, those who haven’t but were considering giving it a go might want some idea of where to dip their beak to get a taste of Sex and the City man-style.
With that in mind, I present to you my worst-to-best list of Entourage...
Season Seven
My oh my, season seven. Where to begin? Season seven of Entourage was what one might equate to being hospitalized after a car crash on your way to a free vacation in Barbados. Not only does it suck that you’re in the hospital and that your car is wrecked, but you’re missing a free holiday. Season seven had no direction whatsoever, it took what was good about season six and got rid of it very quickly. Turtle’s drive to create something by himself the previous season had turned into a luxury limo business, which was fine, until it was killed off almost instantly. Vince’s return to stardom resulted in him being in an action movie, which again, was cool, but after an accident on set, he became an adrenaline junkie and started taking way too much cocaine. Add in dating a porn star and it all just got a bit ridiculous. Drama spent the whole season creating pointless drama and as much as Ari and Eric did their best to save it, the season was just bad.
Season Eight
The final season of Entourage was a mixed bag. Its premiere was actually very good, quickly disposing with the messes of last year and turning Vince into a much more likable guy. Then, the final seven episodes came. With only eight episodes in its run, the eighth season took on way too much to actually get done and the result was a bit of a mess. Ari’s family drama was the only truly consistent theme throughout the season and was probably the highlight, but even with Jeremy Piven delivering some of his best work on the show, it just wasn’t enough. Vince got into a bizarre love affair with a character that came out of nowhere, after another failed business attempt Turtle just accidently became a millionaire and Eric and Drama spent the majority of the season just being annoying. Drama’s story lines are usually pointless, but in this case we were expecting him to make a movie all year that never got made and Eric just had sex for eight episodes. 
Season Four
Season four of Entourage was about one thing: Medellin. Therein lies the problem. The premiere episode was actually fairly clever, taking on a documentary style and following the making of the movie. The remainder of the season was everyone waiting around for the post-production to finish and then selling it to the world. After the trailer leaks online there is a huge buzz around the film and when it gets in to Cannes everything is looking up, until people actually see the film and it completely sucks. The problem I have is that it is just too unbelievable. If it really was as bad as it’s made out to be, how did it get into Cannes in the first place? And if it really is that bad, why does Vince think it’s amazing. Eric sees it for what it is and Ari does his best to sell it, but Vince’s confidence in something so bad kills his career and coincidently, the season. On a side note: Billy Walsh is the stupidest character ever written throughout this season.
Season Six
For a list that is supposed to include the good about Entourage, I bet you’re thinking that things are looking pretty down so far, but fear not, it’s all about to change. Season six is good. Granted there are several parts that don’t quite work, but as a finished product, it definitely works. One of the major differences between the early seasons of the show and the last three are that in the latter, Vince doesn’t do too much. In seasons seven and eight, that doesn’t work too well, but in season six, it’s absolutely fine. With Vince out of the picture, it’s up to his friends to pick up the slack, and that they do. Turtle is probably the stand-out of the season, beginning his aforementioned drive by deciding to go back to college. He also has a girlfriend all season long (Jamie-Lynn Sigler) and their relationship works well. Her decision to leave in the finale was actually almost tear worthy, and they were a big part of why it was a good year. Eric gets himself a real job managing more than just Vince and Drama even has a palatable story arc for the year: losing his job defending honor and then getting a new one in the finale. Ari and Lloyd have some phenomenal moments as Lloyd finally becomes an agent and Ari ultimately becomes the head of the biggest agency in the world.
Season Five
Season five and season six are just about equatable in terms of quality, but season five beats it out for me for one simple reason: Vince. Season five is just about the top of Adrian Grenier’s performance as Vincent Chase as he comes back from the failure of Medellin with a vengeance. After returning from a hideaway in Mexico, he spends the season trying really hard to get back into the business. Constantly being turned down for starring roles, he accepts a supporting role in a film that he absolutely loves and we finally get to see him act. The film ultimately goes uncompleted with budget overruns, but the drive in Vince throughout the season is great. Turtle and Drama don’t do an awful lot throughout the year, but Eric, after the film fails, is fired by Vince. Trying too hard to get him another project, Vince claims that his friend made him look desperate, but when Martin Scorsese drops a call, all is forgiven and the boys are back. 
Season One
Where it all began. It’s really that simple. The first season did a perfect job at introducing the characters at an interesting enough time in their lives to make it more than watchable. We quickly got a sense of what was what and coming in at less than three hours, it’s not difficult to watch the whole thing back-to-back and know where you stand on the show. The season picks up with Vince having just been in a popcorn thriller and making a name for himself in Hollywood. Setting his heart on an indie movie by the name of Queen’s Boulevard, the back half of the season is about the entourage getting Vince into the film. There’s some tension between Vince and Eric and enough celebrity cameos to make it all feel real, creating a very decent (albeit short) season of Entourage.
Season Two
After a pretty great mini-season to kick off the show, the second season is largely more of the same, just on a bigger scale. After returning from making his indie film, Vince is ready for the big time and whilst the group initially struggles to get him a project due to his having fallen off the cool radar, he ends up as Aquaman. The back half of the season is largely pre-production with director James Cameron, and when Queen’s Boulevard makes it into Sundance, the show has one of its best ever episodes. Vince rekindles a love affair with co-star Mandy Moore which works to some extent, but the start of Eric’s relationship with Sloan is the big thing for the season. Ari is not without his screen time either as Lloyd is introduced and when things come to a head in the finale, the two leave mega agency TMA for greener pastures.
Season Three
There are seven other seasons out there, but if you’ve only got time for one, this should be it. Season three has a perfect combination of everything that regularly happens in the show. With Aquaman coming out, there is the rise to superstardom for Vince and, as one of his only clients, it helps Ari quite a bit too. Throughout the season the agent becomes a super agent as he goes from a small office in a broken down building to creating a massive international talent agency. With Ari on the rise, things are looking up, but when Vince sets his sights on Medellin and Ari fails to deliver, the two part ways. The second half of the season becomes all about that and although the resulting project is a disaster, how they got there is very good. Eric fleshes out his relationship with Sloan and Drama gets himself on a hit TV show, with Turtle being the only one not to do much in the way of anything. The fact that the season is almost twice as long as any of the others may be the reason why it’s the best there is, with plenty of time being given to each story, but at only twenty minutes each, twenty episodes really aren’t that hard to get through. 