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Carefree and easy-going, Vincent Chase (Adrian Grenier) is easily considered one of the most likable characters on the HBO series Entourage. His devil-may-care attitude toward his life, career, and finances all make him seem like a fun guy to be around, despite his habit of making poor decisions.

However, upon a closer look, it becomes clear that Vince has some serious issues with his ego, and may even have narcissistic personality disorder. He loves the attention of women, can’t stand rejection of any kind, and often feels entitled to anything his heart desires. 

Even though he’ll always be remembered as one of the most charming playboys to ever grace the screen, he may be toxic than viewers dare to admit.

Vince manipulates Eric Murphy whenever he wants something done

Vince is an extremely charismatic guy and knows how to get what he wants. His good looks and winning smile make him hard to resist, and viewers realize this early on in Entourage. During the entirety of season 1 and several episodes after, his best friend and manager, Eric Murphy (Kevin Connolley), is subjected to all sorts of degrading and inappropriate tasks. 

Whenever Vince is required to do something that he doesn’t want to do, he forces Eric to do it for him. When it’s time to meet with their accountant, Marvin, he makes Eric do the talking. When they need to discuss important issues with his agent, Ari Gold (Jeremy Piven), he sends Eric instead. In the most extreme case, he even forces Eric to set him up with his celebrity crush, Scarlett Johanneson. 

From having Eric sign important documents for him to making Eric wait outside a woman’s house while he hooked up with her, Vince never seems to take much accountability for Eric’s feelings or what he wants. At the conclusion of season 1, their relationship is in dire straits as Eric grows tired of constantly being forced to service Vince with no formal business arrangement. They finally come to an agreement, but only after Vince manipulates Eric into meeting him at the airport by claiming he forgot his wallet.

He feels entitled to whatever project he’s feeling at the moment

Vince is a notoriously difficult client to work with, Ari would tell anyone that. His ego gets in the way of a lot of business and almost ruins his career. Only interested in working on projects he’s interested in, Vince passes on Matterhorn and Aquaman 2, two films that would have set him up for superstardom early in his career.

Although passing on Matterhorn proves not to be that big of an issue, his dismissive attitude toward starring in Aquaman 2 puts him at odds with the studio and its head, Alan Gray (Paul Ben-Victor). To make matters worse, he opts to produce and star in Medellin, an underdeveloped biopic about Pablo Escobar, disregarding the advice of Ari. 

The ensuing damage that’s done to his career is almost irreversible, and he nearly loses everything due to his arrogance.

Vince can’t handle being rejected by women

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‘Entourage’: Quitting ‘Aquaman 2’, ‘Medellin’, and More of Vincent Chase’s Worst Career Moves

Vince has an interesting relationship with women; on the surface, it seems like Vince lives the lifestyle that many men glorify, with many casual flings and tons of women throwing themselves at him. However, his inability to commit to relationships and intense overreaction to women rejecting him shows that he’s got some major intimacy issues. 

When Mandy Moore dumps him and returns to her fiance in season 2, Vince falls into a deep depression and nearly quits Aquaman. In the final season, Vince becomes infatuated with a journalist, Sophia Lear (Alice Eve), who has no interest in him. After she rebuffs his empty advances several times, it appears that he only grows more attracted to her because she doesn’t want him. She eventually gives in and marries him, but it’s revealed that they break up after just 9 days of marriage, further confirming that his feelings weren’t genuine. 

Although there’s no denying that Vince has a good heart and means well, it’s clear that he’s got some flaws as well. Truthfully, beyond the charm and looks, he’s actually quite problematic.