What happens when you lock a four-time Super Bowl champion and a sitcom legend in a room together? Better yet, what happens when you drop them in the middle of a bustling market in Tokyo or a camel trek through the Sahara?
You get the strange, beautiful, and occasionally loud friendship of Henry Winkler and Terry Bradshaw.
Most people know them from different worlds. Winkler is the eternal "Fonz," the guy who defined cool for a generation. Bradshaw is the Steelers icon who now spends his Sundays analyzing football with a mix of expert insight and chaotic humor. They shouldn't really fit. One is a refined New York actor and producer; the other is a boisterous athlete from Louisiana. But when NBC teamed them up for the reality travel show Better Late Than Never in 2016, something clicked.
Honestly, they didn't even know each other before the show. Winkler admitted he didn't know Terry at all before they started filming.
It wasn't just a "coworker" vibe. It became a genuine bond.
The Show That Started It All
The premise was basically The Hangover but with senior citizens and fewer tigers. Henry Winkler and Terry Bradshaw were joined by William Shatner, George Foreman, and comedian Jeff Dye. They traveled through Asia in the first season and Europe in the second.
Winkler wasn't just a star; he was an executive producer. He helped pick this group. He saw something in the mix of these four icons that the rest of us didn't realize we were missing.
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Terry Bradshaw, in his typical fashion, was a bit more blunt about the experience. He talked about being hot, miserable, and "nekkid" during various parts of the trip. He’s a guy who wears his heart (and everything else) on his sleeve. Winkler, on the other hand, brought a sense of wonder. While Terry was complaining about the humidity in Thailand, Henry was soaking in the culture, often acting as the emotional glue for the group.
A Study in Contrasts
You’ve got to love the physical comedy of them standing next to each other. Winkler is famously not a tall man. Bradshaw is a literal giant. Winkler once joked that Terry is "gigantic in every way," from his physical stature to his personality.
There’s this one story Winkler tells about being on a mountaintop. Terry, being affectionate in that heavy-handed way former NFL players are, put his arm around Henry. Winkler claims he walked with a hunch for a week because Bradshaw doesn't know his own strength.
"He needs to hold up a sign when he’s going to show affection," Winkler joked.
But beneath the slapstick, there was a real depth. Bradshaw has been very open about his struggles with clinical depression and anxiety. He’s a guy who uses humor to hide pain. Winkler, who struggled for years with undiagnosed dyslexia, understands what it’s like to have a "mask."
They connected on a level that went beyond their "legend" status. They were just two men in their 70s realizing they still had a lot of life to live.
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What Most People Get Wrong About Their Dynamic
Some viewers thought the bickering on Better Late Than Never was scripted. You know how reality TV usually works—producers whispering in ears to start a fight over a dinner bill.
With Henry Winkler and Terry Bradshaw, it was actually the opposite.
The "stumbling, bumbling personalities," as Bradshaw called them, were completely authentic. If Terry was grumpy because he had to eat something weird (like "chicken vagina" in Asia—yes, that really happened), he wasn't acting. If Henry was getting annoyed with Shatner’s ego, that was real too.
The magic was in how they moved past it.
Lessons from the Road
- Friendship doesn't have an expiration date. These guys were 300 years old collectively and making new best friends.
- Vulnerability is a superpower. Seeing Bradshaw talk about his memory loss or Winkler talk about his family's history in Berlin was more "real" than any Kardashian episode.
- Step out of the comfort zone. Bradshaw hated the heat and the strange food, but he did it. Winkler modeled nude for an art class. If they can do that, what’s our excuse?
Why the Bond Lasted
The show only ran for two seasons, ending around 2018, but the impact stayed. Winkler has often referred to the group as "framily"—friends who become family.
They weren't just "paid to be friends" after a while. The second season, which took them to Europe, felt different. They were tighter. They were looser. They knew which buttons to push and when to offer a hand.
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Winkler once said that the trip was the "gift of a lifetime." For a guy who has won Emmys and played one of the most famous characters in TV history, that’s saying something.
Moving Forward: Actionable Insights for Us "Regular" People
You don't need a network budget to channel the energy of Henry Winkler and Terry Bradshaw. Here is how to actually apply their "Better Late Than Never" philosophy to your own life:
- Audit Your Social Circle: Are you only hanging out with people exactly like you? Try to find your "opposite." If you're the Winkler (the planner, the sensitive one), find a Bradshaw (the loud, spontaneous one).
- Say Yes to the "Ugh" Trip: Bradshaw almost didn't do the show because he didn't want to travel. He ended up loving the bond even if he hated the humidity. Take that trip you're dreading; the people you're with matter more than the destination.
- Share the Struggle: Bradshaw’s openness about his mental health made the group closer. Next time you're with friends, skip the small talk and share something real.
- Keep Moving: Both men are firm believers that retirement isn't the end. Stay active, stay curious, and keep "bumping into" life.
The story of these two reminds us that it's never too late to find a new best friend or a new version of yourself. Whether you’re a fan of the 70s Steelers or 70s sitcoms, the lesson is the same: the best adventures usually happen when you stop worrying about being "cool" and start being human.
Next Steps for Your Own "Bucket List" Adventure:
If you’re inspired by the Winkler-Bradshaw dynamic, start by planning a "micro-adventure" with someone outside your usual bubble. Choose a location within a two-hour drive that neither of you has visited. Focus on the experience rather than the logistics—embrace the "bumbling" just like they did. Success isn't in a perfect itinerary; it's in the stories you tell when you get back.