Of all the HBO series, Entourage might have been the series that has aged the worst. Popular at its time, the years since and critical revaluation have not been kind to Entourage. Focusing on a young movie star, his childhood friends, and his superstar agent, Entourage features a lot of dated comedy, insensitive jokes, and plenty of misogyny. The series was a boy’s show and one that in 2023 certainly doesn’t seem as harmless as it once did.
Set in Hollywood, the series was also known for its celebrity cameos. Some of these cameos were great from acclaimed filmmakers and actors to athletes and musicians. Yet others have dated the series in horrible ways, as many of the cameos feature celebrities who in the years since have had horrible truths revealed about them. Two of the series’ stars, Kevin Connolly and Jeremy Piven, have been accused of sexual misconduct and inappropriate behavior, and the series seemed to court similar company. These are the Entourage cameos that have aged the worst.
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Brett Ratner
Warner Bros.HBO
Brett Ratner plays a “fictionalized” version of himself when Drama comes in to audition for a part in Rush Hour 3. Fictionalized is a bit of a stretch because what the audience sees is very similar to what has been reported about the director. He is surrounded by women dressed in bikinis doing a photo shoot, and seems to be both aggressive and rude. In 2011, Ratner was selected to produce the 84th Academy Awards but stepped down following the use of homophobic language.
In 2017, during the early days of the MeToo movement, six women, including stars Olivia Munn and Natasha Henstridge, accused Ratner of sexual assault and harassment. Elliot Page revealed Ratner harassed them as well on the set of X-Men: The Last Stand. In 2018, star Brendan Fraser revealed that Ratner misled him to pose for pictures that would be part of the director’s book Hilhaven Lodge: The Photo Booth Pictures, even though Fraser never gave permission for the photos to be part of the book. Ratner has since lost his production deal with Warner Bros. and has not directed a movie since 2014.
James Woods
James Woods is a controversial figure, to say the least. The actor guest starred in season three, playing a version of himself who was attending the premiere of the Aquaman movie, as he was the fictional film’s main villain. Woods has not only called himself a vocal Trump supporter but has backed the administration on many controversial views. In 2022, researchers with the University of Washington’s Center for an Informed Public and the Krebs Stamos Group found that the actor was the top purveyor of election misinformation on Twitter at the end of 2020.
In 2017, actress Amber Tamblyn accused Woods of preying on her and her friend when she was underage, and the actor denied it. Funnily enough, in real life James Woods was dropped by his talent agency in 2018 for his political views, so one wonders if his fictional agent Ari Gold would have also.
Jeffrey Tambor
20th Century Fox
Jeffrey Tambor appeared multiple times on Entourage as one of Ari’s more needed clients. The acclaimed actor is known for his work the casts of Arrested Development and Transparent, but in November 2017 the actor was accused of sexual misconduct. Then in 2018, it was reported that while filming Arrested Development in the show’s early years, he blew up in a fit of rage at co-star Jessica Walters. This incident, combined with his sexual harassment on other projects, makes his first scene on Entourage all the more troubling as he references an “incident” on Arrested Development that people did not hear about. Intentional or not, this is an inappropriate joke that did not age well.
Dean Cain
ABC
Dean Cain appeared in season six of Entourage as an actor competing with Johnny Drama for a role. The joke is a swipe at his career, that like Drama, he is a television actor from the ’90s who is still slumming it, yet much of the goodwill Cain had for playing Superman on Lois and Clark: The New Adventures of Superman is now gone.
Not only has Cain been a vocal supporter of the Trump administration, but he has made controversial comments regarding immigration. He has become such a controversial figure that he was killed off-screen on Supergirl, at what seemed like a jab at the actor — his character died helping literal alien immigrants seek safe passage.
Armie Hammer
20th Century Studios
The Entourage movie was highly anticipated by fans, and in keeping with the series, the film featured plenty of cameos and a good number of them have not aged well in the six years since the movie hit theaters. Armie Hammer kicks off one of three troubling cameos. In 2021, Hammer was accused of rape and physical abuse. Hammer has been accused of sexual abuse disguised as a BDSM fetish which includes disturbing comments about cannibalism. Hammer was dropped from multiple film and television projects and has stepped out of the public spotlight.
Piers Morgan
Piers Morgan kicks off the Entourage movie, with his series being used to provide exposition to the audience about who all the characters are. Morgan was already a controversial figure by the time of the film, and in the years since he has only invited more controversy. Morgan has been a vocal supporter of Donald Trump and criticized the Women’s March on Washington after Trump’s inauguration. Morgan has been hypercritical and downright hostile to Meghan, Duchess of Sussex. During his time on Good Morning Britain, he was the subject of thousands of complaints including racist comments. According to a study done by The Sunday Times (via The Hollywood Reporter), Morgan is considered the most hated U.K. personality on Twitter.
Matt Lauer
NBCUniversal
Matt Lauer appeared as himself at the end of the Entourage movie, covering the fictional version of The Golden Globes. Lauer was a staple on television as the host of The Today Show in 1997. In 2017, two years after the release of Entourage, Lauer was terminated by NBC following multiple sexual misconduct complaints filed over the years during his time on The Today Show. Lauer was accused of sexual assault and abusing his position of power over his employees for sexual favors. Reportedly, Harvey Weinstein knew about Lauer’s sexual misconduct and used that knowledge to kill stories about his own sexual assault stories.
Kanye West
Kanye West appeared as himself in season four of Entourage when the popular artist was really only known as a talented if not eccentric musician. In the years since though Kanye West has certainly gone off the deep end and lost a lot of public goodwill. From his controversial feuds with other celebrities like Taylor Swift and Pete Davidson to his support of controversial former president Donald Trump, and recently his anti-Semitic comments that have cost him a great deal of sponsorship. In 2008, a Kanye West cameo felt like a nice surprise; in 2023 it yields a big groan.
Danny Masterson
Netflix
Danny Masterson appears in season two of Entourage, towards the end of That 70s Show tenure. In the years since, Materson’s career has gone downhill quickly. In March 2017, three women filed sexual assault allegations against Masterson, and he was quickly dropped from the Netflix series The Ranch. By the end of 2017, a woman Masterson dated accused Materson of rape, and he was dropped by his agency.
On June 17, 2020, Masterson was charged with raping a 23-year-old woman in 2001, a 28-year-old woman in early 2003, and a 23-year-old woman in late 2003. On November 30, 2022, the trial was declared a mistrial due to the jury being deadlocked in a decision. A new trial is set for March 2023. Masterson is one of the worst-aged cameos on Entourage, and is so disliked that he is the only cast member of That 70s Show not to return for That 90s Show.
Paul Haggis
When Paul Haggis appeared on Entourage, he was an acclaimed filmmaker known for his work on projects like Million Dollar Baby and Crash. He was playing off that image in Entourage, as he was featured as a fictionalized version of himself set to direct a movie about Pablo Escobar that Vince wanted to star in. Haggis was a filmmaker who lent the series a level of credibility that has now been tarnished.
In 2017, Haggis was accused of sexual assault for an incident that occurred in 2013. In 2022, the director was arrested in Italy and charged with aggravated sexual violence and aggravated personal injuries. Haggis has not worked since 2018, and with the charges against him, there is a good chance he won’t, and any luster to his previous films is now forever tainted by his previous actions.
