Eight Sitcom Heroes Who Haven’t Aged Well. Why rewatching feels different now.

TV Comedy| Comedy| Social Commentary in Comedy| Sitcom Analysis, Spotlights, & Deep Dives

February 16, 2026•6 min read

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There’s a particular feeling you get when you rewatch an old sitcom you once loved. Not nostalgia exactly. More a quiet, creeping unease.

You laugh. Then you pause. Then you think, oh… we were meant to like him, weren’t we?

Comedy doesn’t exist in a vacuum. It reflects who we are, who we excuse, and who we centre. For decades, sitcoms were very good at telling us which men were charming, aspirational, and ‘just a bit naughty’. They were cool. They were heroes. We were meant to root for them.

The problem is the characters haven’t changed. We have.

So, here are eight sitcom men who were framed as iconic at the time of broadcast but now feel, at best, uncomfortable and, at worst, deeply creepy.

This isn’t about cancelling comedy. It’s about context. And maybe about admitting that charm has been doing a lot of heavy lifting for a very long time.

Sam Malone – Cheers

Sam Malone was peak 80s sitcom masculinity. Ex-athlete. Bar owner. Confident. Witty. Effortlessly irresistible to women who appeared, slept with him, and vanished by the next episode.

At the time, Sam was framed as a loveable rogue. A man who loved women so much he simply couldn’t help himself. On rewatch, his behaviour looks less like charm and more like entitlement wrapped in a grin.

Sam pursues relentlessly. He ignores boundaries. He treats women as interchangeable experiences rather than people. The show bends around him, rarely asking him to change in any meaningful way.

He was cool because the culture said he was. That coolness has not survived the rewatch.

The Fonz – Happy Days

The Fonz might be the purest example of charisma doing all the work.

Leather jacket. Motorbike. Women falling over themselves. Best friends with teenagers. He barely had to speak. When he did, it was mostly catchphrases and finger guns.

At the time, he was aspirational cool. The fantasy of effortless male dominance without consequence. Watching now, the way women are treated as props in his personal highlight reel feels jarringly dated.

The Fonz isn’t malicious. That’s the point. He never has to be. The world simply rewards him. And that, in hindsight, is exactly the problem.

Gary Sparrow – Goodnight Sweetheart

Gary Sparrow is perhaps the most unsettling on this list because the show desperately wants you on his side.

Gary is a time traveller living a double life, complete with two wives in different eras. This is framed as cheeky wish fulfilment. A man caught between two great loves. A romantic dilemma.

Except neither of those women have agency, no knowledge, and, therefore, no choice.

What once played as laddish fantasy now looks like sustained deception, emotional manipulation, and breathtaking selfishness. The fact the show keeps insisting Gary is a “good bloke really” only makes it worse.

Time travel is not the most unrealistic thing in this sitcom. The moral framing is.

Michael Scott – The Office (US)

Michael Scott is often defended as harmless, lonely, and well-meaning. That defence does not survive sustained attention.

Michael routinely humiliates his staff, crosses boundaries, weaponises his emotions, and expects forgiveness because he is sad. The show wants us to love him. It wants us to believe his intentions matter more than his impact.

This is where Michael becomes more problematic than his UK counterpart. David Brent knows he’s failing. Michael believes he’s succeeding.

He is not a monster. He is worse. He is enabled.

Ross Geller – Friends

Ross was framed as the sensitive one. The nice guy. The romantic.

On rewatch, Ross is jealous, possessive, and emotionally controlling. His relationships are governed by insecurity and entitlement, often played for laughs. His famous “we were on a break” defence has become shorthand for refusing accountability.

At the time, Ross was meant to feel relatable. Now he feels like a cautionary tale about mistaking emotional neediness for emotional depth.

The laughter track of the audience does a lot of work here. Without it, things look very different.

Dave Charnley – Drop the Dead Donkey

Dave Charnley was clever, sharp, and successful. A newsroom alpha with opinions, wit, and a sense of superiority.

He was also casually sexist, emotionally shallow, and endlessly rewarded for behaviour that harmed others. Women were accessories. Colleagues were stepping stones.

What’s uncomfortable now is how familiar he feels. Dave isn’t exaggerated. He’s realistic. The kind of man who thrived because nobody ever asked him to stop.

That realism is what dates him so badly.

Basil Fawlty – Fawlty Towers

Basil Fawlty is still held as a comedy great. Let’s be clear about that.

But he is also a volatile bully whose contempt for women, staff, and anyone he deems inferior is central to the comedy. At the time, his rage was anarchic. A release valve.

Now, it reads as sustained cruelty, softened only by farce.

The brilliance of the performance remains. The character himself feels harder to laugh with and easier to recoil from.

George Costanza – Seinfeld

George Costanza was once seen as the ultimate anti-hero. A man who said the quiet parts out loud. His selfishness was refreshing. His honesty radical.

On rewatch, George is exhausting. He lies constantly, avoids responsibility, resents women, and believes the world owes him happiness simply for existing.

Seinfeld’s genius was refusing to redeem him. The discomfort we feel now is the point finally landing.

George didn’t change. Our patience did.

So where does that leave modern comedy?

Modern sitcoms aren’t suddenly free of problematic men. They’re just more honest about them.

The difference now is framing. Characters are allowed to be selfish, cruel, insecure, or entitled, but the narrative no longer insists we applaud it. Charm isn’t enough. Trauma isn’t an excuse. Being funny doesn’t grant immunity.

That doesn’t make comedy safer or blander. It makes it sharper.

Because when a character behaves badly and the show knows it, the joke lands cleaner, the satire cuts deeper, and the audience gets to laugh without having to quietly excuse anything first.

Comedy didn’t lose its nerve. It finally learned where to aim.

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