The first season of Entourage chronicles Vincent Chase's adventures as he climbs the celebrity ladder after his first successful movie: Head On. At the forefront of the first few episodes is the conflict between Vince's best friend "E" and his agent Ari, who are both working to get the best for Vince, but often differ on how to accomplish this.
Vince's next project is decided halfway through the season: Queens Boulevard. Signed on is indie director Billy Walsh, who comes into immediate conflict with E. Eventually their differences are put aside and the season ends with the start of production on Queens Boulevard, with E formally becoming Vince's manager.
Running subplots include: Turtle's laziness and quest for marijuana; Drama's attempt to follow in his younger brother's footsteps; E dating Ari's assistant Emily (Samaire Armstrong); and Vince's many and varied girlfriends.