I think the most important thing about being a member of an entourage is the responsibility to not only make the "star" look important, but to make them look "powerful" as well. Promotion through bad behaviour is the key to success for the professional "hanger-on". The more "interest" that you can generate for your "star", the more "opportunities" will emerge for them. As a result, this will ensure that you remain in the lifestyle that you have since grown accustomed to.
The larger the entourage means the more frequent these self-preservating acts of "promotion" must be (in order for the group to survive). If Snoop Dogg travels with a 30 man entourage, that means his team has to work 15 times harder than Ryan Seacrest's entourage of 2 (including himself) to not only make sure that Snoop Dogg makes it into the newspapers, but that he can generate the kind of "celebrity status" which allows him to afford the 30 man entourage. Slugging it out with police officers at London's Heathrow Airport is an excellent way to accomplish both.
Hey! For all of you keeping score, this is cartoon number 100 for me :) I really hope that you are (still) enjoying them as much as I am enjoying making them.