The first season of Entourage is a very important season. Without watching it one can be very lost. Vince just got done filming his first leading role in a successful movie, Head On. So now Vince, E, and Ari have to find a new job. The only problem with this is that E and Arie have differing opinions on what is best for Vince. The project that was decided on is Queens Boulevard, a movie perfect for Vince since he grew up in Queens, directed by Billy Walsh. Just like with Ari, E has problems with Billy. They seem to be able to put their problems aside for the movie. Throughout the season E, known for falling in love easily, has relationships with Ari's assistant Emily and a girl named Kristen. Drama tries to recapture his days of a film and television star. Vince lives the celebrity life and has many flings, and Turtle has the easy life of getting high all the time and being Vince's driver. The last episode is when E steps up and tells Vince he wants to be his manager. It does not go so well at first, but before they leave for Queens to begin filming on Queens Boulevard Vince hires E. The first season of Entourage ends with the gang getting on the plane.

All of this sets up for a great season 2 of Entourage.