Troubled 350lbs son of Hollywood icon is forced to humiliating new low… as his movie star brother luxuriates in $7m Montecito mansion

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As a tale of two brothers, the differences couldn’t be more stark.

Josh Brolin, a famous movie star, is enjoying life at his $7.1 million home in Montecito, while his sister, Jess, was recently photographed waiting for a free trolley, according to exclusive photos obtained by the Daily Mail.

Despite both being the sons of Hollywood legends James Brolin, 85, and Barbra Streisand, their children share few similarities, making a family resemblance difficult to see. James and Barbra live together in a $20 million Malibu home.

I often see people struggling with their well-being, and recently I noticed a man named Jess in Ojai, California, who really struck me. He was visibly unwell, with concerning red patches on his legs, and appeared to be carrying a significant amount of weight – around 350 pounds, I’d estimate. He was quietly looking at a simple flip phone while waiting for the bus, and just seemed…lost in thought, a little sad, really. It was a poignant moment, and a reminder that everyone carries their own burdens.

After his money ran out, the 53-year-old man reportedly moved into the Topa Vista Hotel, a local three-star establishment, and is still living there after previously living on the streets.

Okay, so I was scrolling through the Daily Mail, and OH. MY. GOD. It was HIM! Jess! And get this – he was wearing THOSE shorts. You know, the faded blue denim ones from that other photo? I swear he lives in them! Anyway, he was heading to some event at a local school on Sunday, and I nearly lost it. It was the shorts, honestly. The SHORTS!

Jess took a short two-minute bus ride to school, and when he got off, a woman was there to greet him and lead him inside.

The Daily Mail reported previously that Josh Brolin’s brother, who is struggling with personal issues, has been living at the Topa Vista property. This location is on a main highway and is owned by Steve Edelson, a well-known nightclub owner in Los Angeles.

Let’s be real, even if his house isn’t a mansion by Hollywood standards, it’s a huge step up from where he used to live. I always say it’s not about extravagance, it’s about creating a space that feels right for you, and clearly, this does!

By 2011, he had spent the money from the trust fund left to him and Josh by their mother, Jane Agee, and was living in his rundown 1981 Toyota truck.

After three years, the truck finally broke down, and Jess ended up homeless, forced to sleep on the streets. He was even photographed searching through trash for something to eat.

James’s first wife and mother of his children died in a car accident in 1995, ten years after they divorced.

According to his stepmother, Streisand, the family tried to help Jess when he was experiencing homelessness, but he turned down their assistance.

She said in a statement: ‘We love him very much and want only he best for him.’

While Jess was riding the free trolley this weekend, her brother Josh was spotted surfing in Santa Barbara with a large new tattoo on his back.

It is not known if the inked image of a lighthouse framed by topless mermaids is a real tat.

Last month, photos surfaced of Josh on the set of the upcoming thriller, Whalefall, covered in brightly colored, temporary tattoos that looked like artwork.

The brothers grew up with every comfort, first on a ranch in Paso Robles and later in a large mansion in Santa Barbara.

While Josh became a well-known actor in major franchises like The Avengers and Men in Black, his brother appeared in only a couple of films and later worked as a studio runner.

Josh’s success has allowed him to buy a luxurious mansion in Montecito, the same town where Prince Harry and Meghan Markle live, and he enjoys a comfortable life there with his wife, Kathryn Boyd.

Yet despite his gilded background, like his brother he has had his share of drama to say the least.

In his memoir, From Under the Truck, released in November 2024, the actor known for No Country for Old Men described his upbringing as ‘unconventional’.

He shared his battles with addiction and getting clean, which resulted in nine arrests over the years. This included two arrests before he became famous with his part in the movie The Goonies.

The actor, who has been married three times – including to Diane Lane – shared that he lost his close friend to suicide when he was young. He also recounted a difficult experience as a teenager involving a 12-hour LSD trip that went wrong.

Having been sober for years, he recalled a challenging adolescence where he led a double life. He worked as a cook at an Italian restaurant in the evenings and spent his days with a group of friends who were often involved in trouble.

He rode a motorcycle aged four, smoked weed at nine, lost his virginity at 11 and did acid at 13.

While many of his wild companions self-destructed, acting kept him afloat. However, even with those opportunities, he found himself living in a rundown boarding house in Portland, Oregon in 1990, and later, in a small, rented room in New York City in 1992.

His performance in the 2007 film No Country marked a turning point in his career, leading to an Academy Award nomination for Milk the following year and opening doors to major roles in blockbuster movies.

In his memoir, he describes being constantly reminded of his late mother, Jane, who worked as a casting director and later became a wildlife activist. He says she remains a powerful force in his life, even after her death, and he can’t escape her presence.

Maybe if she had survived, who knows where his troubled brother might be now.

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2025-11-25 04:55