Entourage (2004 — 2011)

Entourage (2004–2011), an American comedy-drama series, debuted on HBO in 2004 and concluded in 2011 after eight seasons. Created and mainly written by Doug Ellin, the show follows Vincent Chase – a rising film star – and his childhood friends from Queens, New York City, as they navigate their burgeoning careers in Los Angeles. Mark Wahlberg and Stephen Levinson served as executive producers, drawing inspiration from Wahlberg’s personal journey in the film industry.

Season 1 (2004). In its first season, Entourage follows Vincent Chase’s rise in the entertainment industry after his debut film, Head On. The initial episodes revolve around the tensions between Vince’s friend ‘E’ and his agent Ari, who often clash over methods while still having Vince’s best interests in mind. Midway through the season, Vince begins work on his next project, Queens Boulevard, with indie director Billy Walsh. However, Billy and E immediately butt heads before eventually reconciling. The crew travels to New York for production. Notable side stories include Turtle’s laid-back attitude and search for weed; Drama’s struggle to live up to his younger brother; E dating Ari’s assistant Emily; and Vince’s various romantic relationships.

Season 2 (2005). During season two of Entourage (2004-2011), Vince’s excitement peaked when he received an offer to portray Aquaman in the movie adaptation. However, due to Ari’s inability to secure the contract, Vince found himself in a challenging position. To prove his worth for the role, he needed to impress renowned director James Cameron. This became even more difficult when his ex-girlfriend and co-star, Mandy Moore, announced her engagement during filming. Despite their initial chemistry, Mandy ultimately chose her fiancé over Vince. Although heartbroken at first, Vince found determination to continue with the film. Meanwhile, Ari faced his own struggles as he dealt with Terrance McQuewick’s attempts to steal Vince from him. As their rivalry intensified, Ari was eventually fired from his agency after false allegations were leaked by another agent named Adam Davies.

Season 3 (2006–2007). As Entourage enters its third season, the Aquaman storyline takes center stage as the highly-anticipated movie garners record-breaking success in its opening weekend. However, complications arise when Vince’s passion project Medellin, based on Pablo Escobar’s life, interferes with his commitment to Aquaman 2. Consequently, Vince is axed from both projects by Warner Bros. Meanwhile, E’s romantic involvement with Sloan becomes complicated when he engages in a threesome with her and her friend Tori, whom E finds attractive. The situation escalates when Sloan’s stalker Seth Green confronts E and claims that he had a history with Sloan. But Sloan assures E that Seth was ‘creepy’ and their relationship never went beyond friendship.

Season 4 (2007). During the fourth season, Medellin’s story progresses as production finally commences. Tensions arise when E expresses discontent with the initial cut after Walsh reluctantly agrees to a late-night screening. This leads to clashes between Vince and E regarding creative vision and financing for the film, which escalate throughout the season. Additionally, there is much unease surrounding the ending of the script, resulting in a brief appearance from Stephen Gaghan before Walsh devises what he considers a strong conclusion. When the Medellin trailer is leaked on YouTube, an opportunity presents itself to use the resulting excitement to secure a deal for Vince’s involvement in a new high-budget project.

Season 5 (2008). After enjoying a well-deserved break in Mexico with Turtle, Vince comes back to Los Angeles ready to dive into work. Unfortunately, his movie Medellin did not live up to expectations and received harsh criticism, including Vince’s own performance. However, Eric receives a promising script from two aspiring writers called Nine Brave Souls. Seeing its potential, he gets actors Edward Norton and Carla Gugino on board and renames the film Smoke Jumpers. Ari sees an opportunity to secure the lead role for Vince and encourages Eric to start a bidding war for the movie. Initially hesitant, Amanda eventually joins in on the bidding. But they are outdone by Alan Gray, who fired Vince from Aquaman’s sequel. Determined to get his client the part, Ari challenges Alan to a golf match.

Season 6 (2009). In its sixth season, Entourage (2004-2011) follows individual storylines. Vince, now an A-list actor thanks to Gatsby, is set to star in a biopic about Enzo Ferrari under the direction of Frank Darabont. With little support from his friends, Vince spends most of the season taking it easy. Meanwhile, prompted by his ex-girlfriend Sloan, Eric moves out on his own and eventually shuts down his company to work for veteran manager Murray Berenson. This move angers colleague Scott Lavin who resents Eric’s involvement in the company. Although he starts a relationship with neighbor Ashley, Eric still longs for Sloan and makes attempts to win her back. Turtle also has aspirations of entrepreneurship and begins attending college while maintaining a relationship with Jamie-Lynn Sigler. However, he catches the attention of Brooke, who tries to seduce him during this time at school.

Season 7 (2010). During the filming of The Takeover, directed by Nick Cassavetes, Vince defies the disapproval of Eric and Ari by performing a dangerous driving stunt, resulting in a crash on set. Surprisingly, this setback only fuels Vince’s fearless nature, causing him to seek out more excitement in his life. He impulsively gets a shorter haircut, goes sky-diving, buys a Harley-Davidson, takes Vicodin pills, and even starts a relationship with porn star Sasha Grey. Though initially causing tension between Eric and Vince due to Scott Lavin’s introduction of a new project called Air-Walker, they eventually reconcile and team up to advance Vince’s career.

Season 8 (2011). After a successful stint in rehab, Vince is eager to jump back into his work. Excitement fills him as he presents his new film idea to his circle of friends. Unfortunately, their reaction is not as enthusiastic as he had hoped. Meanwhile, Eric and Sloan’s relationship had ended due to disagreements over a prenuptial agreement. Taking advantage of the situation, Eric and Scott have teamed up to create the ‘Murphy Lavin Group’, taking over Murray Berenson’s agency. While Johnny’s latest project, ‘Johnny’s Bananas’, seems promising for success. In the midst of all this drama, Ari still harbors hope for reconciliation with his wife, only to discover her romantically involved with chef Bobby Flay. This news leaves Ari feeling hurt and seeking solace from Dana Gordon. Adding to the chaos, Turtle carelessly starts a fire in their home with a joint, forcing them all to temporarily relocate to a hotel until the damage can be fixed.