Josh Brolin’s Brother’s Quiet Struggle Sparks Big Questions

Jess Brolin’s life has taken a painful turn that stands in sharp contrast to the success and stability surrounding the rest of his famous family.

While his brother Josh Brolin enjoys a luxury home and a thriving Hollywood career, Jess has spent years battling homelessness, financial collapse, and declining health.

Recent photos of him waiting for a free trolley in Ojai show just how far he has fallen.

His situation has made many revisit the complicated family history that shaped both brothers in very different ways.

The differences between the Brolin brothers are striking and have raised questions about the nature of their relationship.

While Josh Brolin lives comfortably in a $7.1 million Montecito home, Jess was recently photographed sitting slumped on a bench in Ojai, waiting for a free trolley.

In pictures obtained by the Daily Mail, the 53-year-old appeared with red blotches on his legs, weighing an estimated 350 lbs, and wearing the same faded denim shorts he has been seen in before.

He checked his basic flip phone as he stood to catch the arriving bus.

Jess is believed to still be living at the modest Topa Vista Hotel, a three-star property owned by LA nightclub mogul Steve Edelson.

Though simple by Hollywood standards, it is still a major step up from where he once found himself.

After the trust fund left to him by his late mother, Jane Agee, ran out, Jess slipped into homelessness and even lived out of a battered 1981 Toyota truck starting in 2011.

When the vehicle eventually broke down three years later, Jess ended up sleeping on the streets and, at one point, was photographed digging through a dumpster for food.

As Jess moved through another difficult weekend, Josh Brolin was photographed surfing in Santa Barbara, showing off a large tattoo on his back that features a lighthouse surrounded by topless mermaids.

Their different paths are even more noticeable when looking at their upbringing.

The brothers were raised in comfort, first on a ranch in Paso Robles, then in a Santa Barbara mansion.

However, while Josh built an illustrious acting career through roles in “Avengers,” “Men in Black,” and “No Country for Old Men,” Jess appeared in only two films and later worked as a studio runner before his financial and personal decline.

Now, Josh lives in Montecito with his wife Kathryn Boyd, his fame having afforded him a level of stability his younger brother never found.

Despite the differences in their adult lives, Josh’s own history shows how easily things could have turned out differently for him as well.

In his memoir “From Under the Truck,” published in November 2024, the 57-year-old described an “unconventional childhood.”

He wrote about addiction and sobriety struggles that led to him being jailed nine times, including twice before his breakout role in “The Goonies.”

Josh also revealed he lost his best friend to suicide and once endured a frightening 12-hour acid trip as a teenager.

Overall, his early years were chaotic. He rode a motorcycle at four, smoked weed at nine, lost his virginity at 11, and tried acid at 13.

Acting eventually became his escape from destructive habits. Still, he ended up living in a flophouse in Portland in 1990 and later in what he called a “rented cell” in New York City.

His career turnaround came in 2007 with “No Country for Old Men,” which led to his Academy Award nomination for “Milk” and the blockbuster roles that followed.

Much of the brothers’ pain traces back to the death of their mother, Jane Agee.

She died in a car crash in 1995, a decade after divorcing their father, James Brolin.

Jess had inherited a trust fund from her, but when it ran out, he fell into homelessness.

During those years on the street, Barbra Streisand, his stepmother, said the family tried to help, but he refused their support.

According to the Daily Mail, she said in a statement, “We love him very much and want only he best for him.”

Josh also felt the impact of their mother’s death. In his memoir, he wrote that he was still haunted by “the perpetual apparition of Jane,” adding, “She refuses to not be a presence.”

Whether Jess might be today if she had survived remains an unanswered and heartbreaking question.

Josh has fought many demons in his journey to stardom, and the actor has been open about his victories.

In 2021, he celebrated eight years of sobriety, a journey he publicly marked on Instagram with a heartfelt and deeply spiritual message.

As The Blast reported, the Hollywood icon wrote that sobriety taught him to love without always thinking about himself, and he expressed gratitude for being able to feel joy through others.

He added, “God is in everything and that it is made up of every color (and mixture of color) that exists.”

Josh also thanked his wife for supporting him through the toughest times, recalling a 6 a.m. drive when she left him a card next to a photo collage of their children.

For Josh, this “most punk rock sobriety imaginable” was about living gratefully and authentically.