You probably know Woody Harrelson as the guy who made a career out of being the most likable person in the room, even when he's playing a total degenerate. But the real story of the Harrelson boys is way more intense than anything he’s done on screen. Everyone always focuses on his dad—and yeah, being the son of a professional hitman who went down for killing a federal judge is a heavy load to carry—but people usually gloss over the guys who were in the trenches with him. Woody has two brothers, Jordan and Brett Harrelson, and their lives are a wild mix of Hollywood proximity, professional racing, and trying to stay grounded while their family name was plastered across every "true crime" headline in the eighties.
Honestly, it’s a miracle they all turned out as well-adjusted as they did. Their mom, Diane, basically had to be a superhero. She raised them as a single parent in Texas and Ohio while their dad was... well, let's just say he was "traveling."
The Harrelson Brothers: Not Just "The Other Guys"
Woody is the middle child. That explains a lot, doesn't it? The middle-child energy is strong with him. But his brothers aren't just background characters in his biography.
Jordan Harrelson is the oldest of the three. He’s the one who mostly stayed out of the spotlight, which, if we’re being real, is probably the smartest move anyone in that family ever made. Back in the nineties, he was working as an insurance broker in North Carolina. Eventually, he made his way back to Midland, Texas. Imagine being an insurance guy in a small town while your brother is winning Emmys and your dad is in a Supermax prison. It's a weird contrast. Jordan has described his childhood as "tough," mainly because they were poor and their mom was doing the work of two parents. He’s been described by people who’ve met him as "down to earth," which is high praise considering the chaos he grew up around.
Then you’ve got Brett Harrelson, the youngest. He’s the one who followed Woody to California.
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Brett is a bit of a renaissance man, or maybe just a guy who gets bored easily. He tried the acting thing for a while, even appearing in The People vs. Larry Flynt alongside Woody. But acting wasn't really his "thing" in the long run. He pivoted to professional motorcycle racing. He wasn't just a hobbyist, either—the guy was ranked number eight in the country at one point. He eventually quit after seeing too many people get seriously hurt or killed on the track. Today, he’s heavily involved in the legal cannabis and CBD industry, co-founding "Harrelson’s Own." He’s a long-time vegan and a massive activist, much like his big brother.
Growing Up in the Shadow of Charles Harrelson
You can't talk about the Woody Harrelson siblings without talking about their father, Charles. It’s the elephant in the room that never leaves.
When Woody was about seven, Charles just... left. He disappeared from their Houston home in 1968. The boys didn't really see him again until 1981, when the news broke that he’d been arrested for the assassination of Judge John H. Wood Jr. in San Antonio.
Think about that for a second. You’re a young adult, your brother is starting to get famous on a show called Cheers, and suddenly you find out your dad is the most notorious hitman in America.
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- Woody has been pretty open about having "mixed feelings." He actually helped fund his father's appeals for years, trying to get him a new trial. He saw his dad as charming and well-read, but maybe not much of a "father" in the traditional sense.
- Brett has been even more vocal lately. He co-produced a podcast called Son of a Hitman where he really dug into the trial. He’s gone on record saying he’s not entirely convinced his dad got a fair shake or was even guilty of that specific crime.
- Jordan participated in that podcast too. He’s talked about the "rage" and the struggle of growing up without a father figure, only to have that father reappear as a convicted killer.
That Matthew McConaughey "Brother" Rumor
Okay, we have to talk about the Matthew McConaughey thing. It sounds like a plot from a bad sitcom, but they’re actually serious about it.
The story goes that back in the day, Matthew’s mom, Mary Kathlene McCabe, "knew" Charles Harrelson. And by "knew," we mean she was apparently having a fling with him right around the time Matthew was conceived. Woody and Matthew are already best friends—they call each other "brothers" anyway—but the possibility that they are actual half-brothers has been a huge talking point.
Brett Harrelson has been the one stirring the pot lately. In early 2025, he was spotted out and about saying he’s ready to "pinch some hairs" for a DNA test. According to Brett, Woody is all for it, but Matthew is the one hesitating. It makes sense—if Matthew finds out his dad isn't his biological dad, his whole world shifts. But for the Harrelson brothers, adding another "brother" to the mix just seems like a Tuesday.
What This Means for You
Looking at the lives of Woody Harrelson's siblings gives you a much better perspective on why Woody is the way he is. He’s not just a "quirky" actor; he’s a guy who survived a pretty traumatic upbringing alongside two brothers who were his only real support system.
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If you’re interested in the deeper story, here’s how to dive in:
- Listen to the "Son of a Hitman" podcast. It’s a 10-part series that features both Brett and Jordan. It’s probably the most honest look you’ll ever get at their family dynamic.
- Watch "The People vs. Larry Flynt." It’s one of the few times you can see Woody and Brett on screen together, playing brothers. The chemistry is real because, well, it is.
- Check out Brett’s work in the CBD space. If you’re into the wellness side of things, seeing how the Harrelsons have pivoted their family name into activism and business is actually pretty interesting.
The Harrelson story isn't just about one famous actor. It’s a story about three guys who had every reason to fail but ended up finding their own versions of success—whether that’s in a boardroom, on a racetrack, or just living a quiet life in Texas.
To see more of the Harrelson family's public interactions, you can follow Woody’s official social media accounts or look into the latest updates regarding their upcoming Apple TV+ series, Brother From Another Mother, which lean heavily into the McConaughey-Harrelson bond.