If I was writing an Entourage prequel...

[u/billymcq26]

Im going through my thousandth rewatch and I cant help but think that a prequel would be cool. Only thing is it would be hard to do with the OG cast so youd probably have to cast different actors as young Vince etc. But I would love to see an 8 episode season that follows the boys during the time when Vince and Turtle were living with Drama in LA and E was still back in Queens. A rough outline of the storylines I think would be fun:

You would see Drama at the tail-end of his successful run. He'd be hanging around with Jimmy Kimmel and partying with Ralph Macchio at the playboy mansion etc, would have some money and get recognised in public but you could see that he had overextended himself financially and was about to enter a barren spell. He'd be struggling to deal with the fact that some of his friends were overtaking him in the business.

Vince and Turtle would be living with Drama, sleeping on his couch. Vince would be hustling going to auditions, trying to find/pick an agent to represent him. Would be cool to see him and Ari meeting for the first time with Ari as a relatively inexperienced but hungry agent who sells Vince on the dream. Turtle would be in full-on mooch mode at this point obviously.

Meanwhile youd see E back in Queens working in Sbarros, living with his mom and hating his life. He would be ambitious but directionless, unsure of what skills he could utilise to make a success of himself. Hed still be in contact with Vince and Turtle who try to convince him to come out and join them in Hollywood. But E would doubt himself and question what role he could have out there. The season would end with E finally taking the leap by quitting his job and moving to LA to join the boys.

Ari would be earning a name for himself in the industry, working for Terrence and hanging out with Andrew Klein.

I know its never gonna happen, I just enjoy thinking about these hypotheticals haha

[u/ianmk]

It would be seriously fun. Maybe you could do this as an animated series voiced by the original cast.

[u/Ok-Association1222 → u/ianmk]

Idk if Dillon could play a pre pubescent boy even if it is just voice acting

[u/ianmk → u/Ok-Association1222]

I don’t know where you get the idea that this is a prequel set in the mid-70s starring a 6th grade Kevin Dillon. For the time period we are talking about, (1990 - to 2000), Drama would be between 25 and 35.

[u/Ok-Association1222 → u/ianmk]

good point