‘Entourage’: Vincent Chase’s Top 5 Worst Financial Decisions

One of the most appealing things about watching the HBO series Entourage was the fantasy it provided for viewers. Although its subject matter was at times problematic, Entourage provided an imaginary glimpse into celebrity life that many people crave.

Movie star Vincent Chase (Adrian Grenier), in particular, lived a carefree lifestyle and took crazy risks that none of us, in reality, would ever dream of. He often spent his money freely and never paid much attention to his finances, much to his accountant Marvin’s (Paul Herman) chagrin. 

Here are some of the most outrageous financial decisions Vince made over the course of the show.

Vince leases a Rolls Royce Phantom to distract himself

In season 1, Vince is still a rising star that’s making a name for himself in Hollywood. Because of this, it’s very important that Head On, his breakout movie, does well. His agent, Ari Gold (Jeremy Piven), is feeling the pressure and encourages his manager Eric Murphy (Kevin Connolley) to take Vince’s mind off of a bad review the film has gotten. 

Eric misinterprets Ari’s request and the guys decide to buy a $320,000 Rolls Royce Phantom to distract themselves. Vince’s accountant berates Eric for the irresponsible financial move, and Ari chews him out for blaming the decision on him. 

By the end of the episode, Vince decides that he doesn’t want the car anymore, but they’ve already signed a 3-year lease on it. Eric makes note of this, but all Vince says in response is “You’ll figure it out.”

He buys a house that costs 4 times his budget

In season 2, Vince has become a more established actor and is looking for better roles. He’s on the shortlist as the lead for a studio’s new Aquaman franchise but doesn’t want to play a superhero and be typecast. 

Meanwhile, he’s looking for a new home and has been given a $1,000,000 budget by his accountant. The home he initially views within that price range doesn’t impress the crew, so his realtor takes them to Marlon Brando’s old home instead, which costs $4,300,000. 

Despite not having a job, Vince decides to purchase the home against Eric’s wishes. Once again, their accountant is not happy. Luckily, he lands the role of Aquaman later in the season.

The unemployed actor spends $20,000 on sneakers for his friend

Adrian Grenier
Adrian Grenier | David M. Benett/WireImage)

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Vince buying things without a job seems to be a recurring theme of the show. In season 3, Turtle (Jerry Ferrara) misses out on getting a pair of limited edition Air Force 1s because Vince refuses to use his star power to skip the line at a store. 

To make it up to him, Vince decides to reach out to the shoe’s designer personally to make Turtle his own pair. In the end, Turtle gets to meet Fukijama, the designer, in person and gets a 1-of-1 pair. 

However, the role in a Ramones project Vince was pursuing falls through due to a blunder by Ari. To make matters worse, he’s already spent $20,000 on Turtle’s new sneakers.

He sells all of his possessions to buy a script

In arguably the worst move of his career, Vince decides he wants to produce Medellin, a biopic about Pablo Escobar, on his own. He gets into a bidding war with a wealthy Hollywood producer, even though—you guessed it—he’s out of work. 

As the bidding war escalates, he puts all of his assets on the line, selling his home and cars, and emptying his bank accounts to buy the script for $5,000,000. 

He gets the script, but the poorly-produced film ends up being a box office bomb that sends his career—and life—into a tailspin.

Vince bets $100,000 on a soccer match—twice

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After shooting Medellin, Vince’s life and career are up in the air as the crew tries to find a studio to distribute the film. Despite this, Vince continues to live without worry.

While taking a trip to Malibu one day, he runs into a random woman who asks him to spend the day at the beach with her. When they arrive at the beach house, she reveals that it’s Dennis Hopper’s, as he’s a friend of her father. 

Upon meeting him, Vince is enamored, and Hopper talks him into betting $100,000 on a soccer match he knows nothing about. Vince still has no money or job, but he sticks it out and luckily loses no money because Hopper’s friend forgot to call in the bets.

Further pressing his luck, Vince bets on the next match, wins the bet, and goes home with $100,000. Only on Entourage.