You probably think of the leather jacket first. Maybe the "Ayyy!" and the office in the bathroom. It's almost impossible to talk about tv series with henry winkler without starting at Arnold’s Drive-In. But honestly, if you stop there, you’re missing one of the most wild second acts in Hollywood history.
Henry Winkler is a survivor.
He didn't just play a cool guy once; he spent decades reinventing what "cool" actually looks like. From a bumbling lawyer to a self-absorbed acting teacher, the man has range that most actors would kill for.
The Shadow of the Leather Jacket
Let’s be real: Happy Days was a juggernaut. It ran from 1974 to 1984, and for a solid decade, Arthur Fonzarelli was the most famous man on the planet. Winkler was getting 55,000 fan letters a week. Think about that. That's a stadium's worth of mail every seven days.
But there was a catch.
Winkler was so good as Fonzie that the industry basically forgot he was an actor. They thought he was the Fonz. When the show ended, he couldn't get a job. For eight or nine years, the phone just didn't ring for acting parts. He was typecast in the most brutal way.
Instead of fading away, he went behind the scenes. Did you know he was an executive producer on the original MacGyver? Yeah, the guy who could fix a plane with a paperclip and some gum exists because the Fonz saw potential in the script. He also directed movies like Cop and a Half and Memories of Me.
He wasn't acting, but he was building.
The Renaissance: From Arrested Development to Barry
Then came 2003.
Mitch Hurwitz cast him as Barry Zuckerkorn in Arrested Development. If you haven't seen it, Barry is quite possibly the worst lawyer ever to grace a television screen. He’s the polar opposite of Fonzie. Where Fonzie was competent and effortless, Barry is a mess who constantly gets "excited" by things he shouldn't and gives terrible legal advice.
It was a stroke of genius. It reminded everyone that Winkler was funny—not just sitcom funny, but weird, meta, "I'm-in-on-the-joke" funny.
The Gene Cousineau Era
If Arrested Development was the spark, Barry was the wildfire.
Playing Gene Cousineau on the HBO dark comedy Barry (2018–2023) changed everything. Gene is a pretentious, failed-actor-turned-teacher who is somehow both lovable and completely exhausting. Winkler finally won his first Primetime Emmy for this role at the age of 72.
He waited 42 years between his first nomination for Happy Days and that win. Talk about a long game.
What’s fascinating about his turn in Barry is how he uses his own history. Gene is a man obsessed with his "craft," even when that craft is barely paying the bills. Winkler brought a warmth to the character that wasn't originally on the page. In early drafts, Gene was much meaner. Winkler made him human.
A Career Built on Overcoming
Most people don't realize that during the height of Happy Days, Winkler was struggling.
He has severe dyslexia. He wasn't even diagnosed until he was 31. Imagine being the biggest star in the world and being terrified of the Monday morning table reads because you can't read the script. He used to memorize his lines by having someone read them to him, or he’d just improvise based on the "vibe" of the scene.
He turned that struggle into a legacy. He’s written over 30 children's books about Hank Zipzer, a kid with dyslexia.
- Parks and Recreation: He played Dr. Saperstein (Jean-Ralphio’s dad). Pure chaos.
- Royal Pains: He was Eddie R. Lawson, the unreliable but charming father.
- Childrens Hospital: He played Sy Mittleman, a role that let him get truly bizarre.
- Monsters at Work: Even in voice acting, he brings that specific Winkler energy to Fritz.
What to Watch Right Now
If you want to see the full evolution of tv series with henry winkler, don't just stick to the classics.
Start with Barry. It is the definitive modern Winkler performance. It shows the ego, the heartbreak, and the comedy of a man who has seen it all. Then, go back and watch Arrested Development. Pay attention to the "jumping the shark" joke in Season 2—it’s a direct wink to his Happy Days past that only a true expert would catch.
He even did a reality travel show called Better Late Than Never with William Shatner and George Foreman. It’s surprisingly sweet.
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Winkler’s career teaches us that you're never actually "stuck" in one lane. You might be the guy in the leather jacket for a minute, but if you're willing to produce, write, and wait for the right weird role, you can end up as an Emmy-winning legend decades later.
Next Steps for Fans:
- Watch the first season of Barry to see why he finally won that Emmy.
- Check out the Hank Zipzer series (both the books and the BBC show) if you have kids who learn differently.
- Revisit Arrested Development specifically for the Barry Zuckerkorn scenes—they're masterclasses in comedic timing.