NETWORK: HBO
AIR DATE: September 7, 2008
STARRING: Adrian Grenier, Kevin Connolly, Kevin Dillon, Jerry Ferrara, Rex Lee, and Jeremy Piven
CREATED BY: Doug Ellin

The boys are finally back and ready for what could be the most important season of their show's career. The interesting thing about Entourage is that the show's initial success and a lot of its charm was centered around being hip and new. There was nothing on the air that felt like Entourage. Hot young stars, the hippest places in Hollywood, and the show's fresh take on the cult of celebrity helped make the first four seasons of Entourage some of the most interesting television of the last ten years. But how does a show based on being fresh and new get older? We're in the FIFTH season of Entourage here. As Chris Rock says, "No one wants to be the oldest guy at the bar." There's still a lot to like about Entourage but a stale and overly familiar quality is definitely starting to seep into Doug Ellin's once-brilliant creation. Like a band who tries to release the same album one too many times, the team behind Entourage are going to have to learn a new tune very soon. This is still one of the best ensembles on television and there are enough funny moments in the first two episodes of the fifth season of Entourage to warrant viewing but it's hard to shake the feeling that Entourage is revving its engines and preparing to jump the shark. This Entourage may need an intervention.

The writers of Entourage open the fifth season, a year after the last one, and everyone is STILL talking about Medellin, the doomed project that brought down both the careers of Vinny Chase (Adrien Grenier) and arguably the show itself. They spent way too much time on Medellin. But it looks like we're finally moving on. In the premiere, Vinny and Turtle (Jerry Ferrara) are hanging out in Mexico, drinking tequila and banging beautiful women. Not a bad life. Eric is trying to financially get over the failure of Medellin, which we see getting ripped in half by Roeper and Phillips in the premiere episode. (There's a bitter irony in the fact that the two Chicago critics are no longer on the air that adds to the "stale" nature of the premiere, even if Ari's reaction to Roeper is hilarious.) Meanwhile, Drama gets a plotline that feels like one that was discarded in season one or two about how he only likes to be photographed from one side. A script offer comes in that could save Vinny's career. The problem is that the script is horrendously titled "Danger Beach", which everyone claims is just a working title. Ari, Eric, and Drama head down to Mexico to try and talk their boy into coming back and taking what could be his last chance at a career. Beautiful babes, gorgeous sunsets, and enough tequila to kill a horse...or "Danger Beach"? It's a tough sell.

Let me make something clear - I still love Entourage. The critical edge in this review is the same kind of tough love that Ari gives his favorite client. The fact is - the first two episodes of the fifth season of Entourage do not live up to this show's potential. Drama, Turtle, Ari - their acts are all getting stale. Ironically, Sex and the City suffered a similar "boredom by character familiarity" around this point in its series' trajectory and there's always been a direct parallel between the four gents in Entourage and the quartet of SATC. (Maybe we'll get an Entourage movie around 2012.) Entourage really needs to shake things up in the fifth season. By the end of episode two, Vince seems to be confident again, having met a cute girl (the great Leighton Meester of Gossip Girl fame), Eric is chasing down a couple of promising screenwriters (Lucas Haas and Giovanni Ribisi) who happen to be rednecks, and Turtle, Ari, and Drama are up to typical hijinks. Wouldn't it have been great to watch Vinny truly suffer through a career crisis instead of bouncing back so quickly? What if the foursome actually split for a while? What if Drama had a girlfriend for a while? What if Turtle had his own plotline? Just like Vinny's career, Entourage is at a turning point. You can never count out writers and actors this talented and, like I said, there's more than enough quality acting and writing here to recommend the fifth season of Entourage, but you should also expect more from people who produced something that was once one of the best shows on television and now feels like a shadow of its former self.

Note: If you want to see how the boys got to this point, check out the fourth season of Entourage, which was released in a very impressive HBO set on August 26th. The 12 episodes that aired in 2007 and focused on the production of the always-doomed Medellin are presented in a 3-disc set with perfect 1.78:1 anamorphic widescreen and 5.1 Dolby Digital Sound. HBO has always been a pioneer in television and it does seem like a mistake that they're not quickly jumping on the Blu-Ray bandwagon, but these episodes look as good as standard TV on DVD can be. Special features inclue a panel of the cast from the US Comedy Arts Festival, a making-of Medellin featurette, a Medellin trailer, and three commentary tracks.