The last series I watched before this was the final season of The Wire. Absolutely brilliant television, but man does it take a lot out of you. Thankfully there wasn't an ambiguous, Sopranos-esque ending, but in some ways it would have been better. Watching the endings for some of the characters was heartbreaking, especially after you've followed them for years.
Anyway, there's not a lot of this in Entourage. If The Wire is about the consequences of actions - both by individuals and institutions - Entourage is about the complete absence of consequences. Vince and his posse run out of money? No problem, through some crazy turn of events, he'll get a multi-million dollar job offer the next episode.
Season five does show the guys struggling a little bit, with Vince's vanity project Medellin struggling to find a buyer, and everyone crashing at Johnny's new apartment. You never really get the feel that it's permanent though, it's just a small speedhump on their way to an even more lavish lifestyle.

What I did like about season five was there was a lot of Billy Walsh, probably the best character on the show outside of Ari. For some reason he always reminded me of my friend Boris Djuric. Anyway, his constant verbal battles with both E and Ari are a definite highlight of the show. The writing seems to be a little below the standard of the first two seasons, there's not quite as many classic Ari lines in each episode, but there's still enough to make it laugh out loud funny every now and then.
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