Welcome back to the Deep Dive. We grab all the
source material, the articles, interviews, the
backstory, and try to piece together a really
clear picture for you on, well, often pretty
fascinating topics. And today, yeah, we're looking
at someone whose career took a turn that's honestly
kind of mind -blowing. It really makes you rethink
one of the most recognizable faces in cult movies.
We're talking about Alexander Ross Winter. Right.
And for pretty much everyone, the name instantly
brings up Bill S. Preston, Esquire. You know,
the excellent dude, time traveling, air guitar
shredding, the whole Bill and Ted thing. That's
the global image, absolutely. The 89, excellent
adventure, then bogus journey in 91, and that
great comeback with Face the Music just a few
years ago in 2020. But here's the thing, and
this is really the core of our deep dive today.
If you only think of Alex Winter as, you know,
that beloved actor, well, you're missing out
on like two decades of... Really intense, critically
praised and seriously engaged work. Yeah. As
a documentarian, an activist. Exactly. So our
mission really is to unpack how that happened.
How does the star of an 80s teen comedy become
this like. expert investigative filmmaker focusing
on the dark web global finance big corporations
big tech it's more than just switching jobs right
it feels like a whole different purpose a total
shift in focus and the timing now looking at
it from 2025 is super interesting because he's
somehow managing to do both things like full
force totally like on one side he did that gonzo
horror comedy destroy all neighbors in 2024 just
completely out there and then on the other side
this fall He's going back to where it all began
for him, essentially. That's right. Back to Broadway.
He's co -starring with Keanu Reeves again, which
is amazing in itself. Wow. In a major revival
of Samuel Beckett's Waiting for Godot, Jamie
Lloyd is directing. Okay, so you've got gonzo
comedy, serious documentaries about tech and
finance, and then... philosophical stage drama.
It's a stunning mix. It really shows how he's
pulling off this completely unexpected career
pivot with just relentless energy. So let's dig
into how he got here. OK, so to really get the
filmmaker and the activist side of Alex Winter.
We got to rewind. We need to look at the foundation,
the artistic world he grew up in, because he
wasn't just like discovered walking down the
street in Hollywood. No, definitely not. He was
born in London, July 17, 1965. He actually holds
dual British and American citizenship. But the
really key thing, like you said, is his parents.
They were professional dancers. Right. So that
world was disciplined, artistic. Deeply. His
mom, Greg Mayer, she was American, born in New
York, and she trained with Martha Graham. Like
the Martha Graham. Wow. The pioneer of modern
dance. Exactly. And she founded her own modern
dance company in London back in the mid 60s.
And his dad, Ross Albert Winter, who's Australian,
he actually danced with her troupe. So this is
serious avant -garde performance in his DNA,
basically. Pretty much. Then when Alex was about
five, the family moved over to St. Louis, Missouri.
His parents started another company there, the
Mid -American Dance Company. So Alex, as a kid,
he got formal dance training. He learned that
discipline, the physical rigor you need for that
kind of work. The kind you need for Broadway
or, you know, professional dance. Right. And
even though his parents split up in 73, that
performance background stuck with him. In 1978,
he moved with his mom to Montclair. New Jersey.
And that move was basically the key that unlocked
his first career break. The stage. The stage,
yeah. That's the part people often miss. They
think Lost Boys or Bill and Ted was the start.
But no, he was a working actor commuting into
New York City way before all that. He was doing
Broadway, off -Broadway. Yeah, look at the record.
He was in some pretty big shows, like he was
a replacement in The King and I back in 77, 78.
And he played John Darling. That's a key part
in the Peter Pan revival in 79. Right. And by
81, he's doing Simon Gray's close of play at
the Manhattan Theater Club. That's serious theater.
It shows he was comfortable with that world,
with complex plays, ensemble work, which makes
his return to Godot now in 2025 feel like a real
full circle thing, not just some celebrity stunt
casting. Absolutely. And there's another layer,
too, culturally. His mom's Jewish, Ukrainian
Jewish descent. The family wasn't super religious,
but he did go to Jewish summer camp, apparently
learned some Yiddish from his grandmother. So
you have that mixed to the dual citizenship,
the cultural background. Interesting. But even
with that stage success, it seems like his head
was already turning towards making things himself.
Totally. In 1983, he gets into NYU's Tisch School
of the Arts. That's a big sign right there. He
wasn't just trying to act, he wanted to direct.
And that's where he met Tom Stern. That's the
guy. Crucial collaborator. They hit it off, started
making 16mm short films together almost immediately.
Classic film school story. Did he finish Dish?
He actually didn't. Dropped out before senior
year, which, you know, happens a lot with young
directors who are just itching to get started.
He moved out to Hollywood specifically to write
and direct. But Hollywood being Hollywood, you
got to pay the bills. Exactly. So while he's
trying to get short films and music videos off
the ground, he lands that role. The one people
do remember from before Bill and Ted. Marco.
And the Lost Boys. Marco the Vampire, yeah. 1987,
Joel Schumacher film. Total classic now. And
that role, that visibility, it was kind of the
perfect setup. Raising his profile just in time
for the part that would, well, change everything.
So Bill and Ted blows up. Huge global success.
That gives Alex Winter what every aspiring director
needs. Fame, access, basically currency in Hollywood.
Right. But what's really striking is how fast
he refused to just stay Bill. He cashed in that
currency, sure, but he used it to push his own
vision, starting with sketch comedy. Right after
Bogus Journey in 91, yeah. Him, Tom Stern, and
another collaborator, Tim Burns, they launched
the Idiot Box on MTV. Super fast -paced, really
weird sketch show. Didn't last long, though,
did it? Only six episodes. But it definitely
showed off their unique kind of bizarre humor,
and that little bit of cult buzz, plus the Bill
and Ted heat, led straight to a studio deal.
Okay, see, that's the smart play. Totally strategic.
They leveraged that momentum into a pretty big
deal. deal, like $12 million from 20th Century
Fox. But what they gave Fox was definitely not
Bill and Ted 3. No kidding. We're talking about
Freaked, 1993, his first time directing a feature
film. Co -directed with Stern, co -wrote it,
and he starred as the main guy, Ricky Coogan.
How would you even describe Freaked to someone
who hasn't seen it compared to Excellent Adventure?
It's like night and day, a quantum leap into
weirdness. Freaked is this Totally surreal, satirical,
body horror comedy. It's just packed with insane
creature makeup, crazy practical effects, and
it's savaging corporate culture, fame, media.
It sounds completely nuts. It's completely nuts.
It shows right away he had this audacious streak.
Like, you gave us $12 million. Okay, we're going
to make the weirdest possible thing with it,
totally uncomplicated. It's basically the definition
of an anti -studio film made by a studio. and
didn't get good reviews yeah surprisingly like
the new york times entertainment weekly they
reviewed it well at the time but fox they clearly
had zero idea what to do with it how do you market
that level of stranger they just did pretty much
buried it never got a wide release which is a
shame but it did eventually find its audience
became this huge cult favorite later on through
video and stuff still having your first big movie
basically shelved by the studio That must have
stung. Seems like it. Because he took a break
from feature directing after that. A pretty long
one, actually. Didn't direct another feature
until 99. Almost seven years. And when he came
back, it was a completely different vibe again.
Totally different. Fever. A psychological thriller.
And this is where people outside the, you know,
cult movie world started to really take notice
of him as a serious filmmaker. It got some real
recognition, didn't it? Huge validation. Fever
got into the director's fortnight at Cannes.
That's a major deal for independent art focused
cinema. And the critics really responded. The
New York Daily News called it a claustrophobic
mind bender worthy of Roman Polanski. Wow. From
Bill S. Preston to comparisons with Polanski.
That's quite a leap. Right. But then almost immediately
after that, in the mid 2000s, he pivots again,
this time into kids TV blockbusters. It feels
like whiplash just talking about it. Fever, then
Ben 10. Is that just about the money, you think?
Or did he genuinely want to try family stuff?
It definitely shows his range. But yeah, very
likely a smart move financially to keep his independence.
You got to have some commercial hits if you want
to fund the weirder passion projects down the
line. And he jumped into adapting Ben 10, which
was massive for Cartoon Network. And these weren't
small things either. The first one, Ben 10, Race
Against Time in 2007. Didn't that break records
for the channel? Highest ratings in their history
at that point. Yeah. Then he did the sequel,
Ben 10. Alien Swarm in 2009. That pulled in like
16 million viewers over its opening weekend.
That's insane for cable TV. blockbuster numbers
really so that whole period proved he wasn't
just the freaked guy or the fever guy he was
also a super competent bankable director who
could handle big budgets effects huge audiences
it's hard to imagine him getting the funding
for his later really complex documentaries without
showing he could deliver both niche art house
stuff and massive mainstream hits okay so now
we get to the era that arguably defines his career
now the documentarian era And it wasn't like
he just fell into it. It seems like a very deliberate
shift towards serious investigative work, mostly
focused on tech, privacy, media. These big power
structures. Yeah, it seems rooted in a real genuine
fascination with the Internet, not just the tech
itself, but the culture it created. Winter said
he was really struck by the community aspect
early on, how tons of people could talk about
anything and everything anonymously. He saw something
huge starting and he wanted to document it. Which
led straight to his first big documentary, right?
Yeah. About Napster and file sharing. Exactly.
And right away you see his critical thinking.
With Downloaded, he wasn't just repeating the
standard line about, you know, piracy killed
the music industry. Right, the easy narrative.
He was actually pushing back against that, criticizing
media companies, news outlets for, like, exaggerating
how many people use Napster only for illegal
stuff. He wanted to show the revolutionary side
of it, how it changed access to culture. He wasn't
buying the simple story. He wanted the deeper,
maybe more complicated truth. Precisely. And
that drive for the technical, complex truth led
him to what's probably his most well -known doc,
Deep Web in 2015. Which won a ton of awards.
Multi -award winning, yeah. Deep Web tackled
some heady stuff. The Silk Road, online black
market. Bitcoin, back when it was still pretty
mysterious to most people, the whole idea of
the dark web. It premiered at South by Southwest,
right? Yeah. And did really well commercially.
Huge for a doc. Opened as the number one documentary
on iTunes, which tells you people were hungry
for this kind of information. And the Silk Road
story itself is fascinating. Focused a lot on
Ross Ulbricht, the founder who got, what, life
in prison. Yeah. Sentenced to life. Winters'
film didn't just explain how the market worked.
It dove into that whole high -profile legal fight,
asking big questions about government power online,
anonymity, digital freedom. Where are the lines?
What's really interesting is seeing the connections
he makes. If Napster was about anonymous information
sharing, his next films kind of follow the trail
of anonymity into money and power. That definitely
seems to be the thread. It leads straight into
global finance. He put out two documentaries.
basically back to back in 2018 that hit on similar
themes. Right. First was the Panama Papers, all
about that massive leak of financial documents
in 2016. Which exposed all those offshore shell
companies. Exactly. These like secret tools used
everywhere to hide money, dodge taxes, basically
operate in the shadows on a massive scale. Winter
used the documentary to show why this hidden
world of finance actually matters to regular
people, why that anonymity is a problem. And
the second one. that year looked at the tech
side again. Trust Machine, the story of blockchain.
So looking at the technology behind Bitcoin and
crypto, he explored the potential decentralization,
transparency, all the promises, but also looked
critically at how it was really playing out,
connecting it back to the financial systems he
looked at in Deep Web and Panama Papers. OK,
so there's a clear line. Anonymous culture with
Napster, anonymous transactions with Bitcoin
and the dark web, anonymous wealth with the Panama
Papers. He's using his camera to look into these
hidden systems, these places where power operates
unseen. It's a really consistent investigation.
But he wasn't only focused on tech and finance,
right? He also turned his lens onto culture and
Hollywood itself. like showbiz kids in 2020 yeah
that was a really powerful one looking at the
reality of being a child actor the pressure the
intensity sometimes the danger given his own
background that felt very personal and then the
huge one also in 2020 zappa oh yeah the frank
zappa documentary that was a monumental project
and it really speaks to the trust and credibility
he'd built by then because he got full access
to the zappa family trust archives which are
famously Tightly controlled. How did he swing
that? It wasn't just handed to him. It came from
the fans. They crowdfunded it through Kickstarter.
It actually became the highest funded documentary
ever on Kickstarter, raised over $1 .12 million.
Wow. That's incredible. People really wanted
him to tell that story. Definitely. They trusted
his vision as someone who could handle that legacy
properly. And then his most recent big doc, the
YouTube effect from 2023, brings it right back
to the Internet's power structures. Looking at
YouTube's massive influence. Yeah. Produced with
Gail Ann Hurd. big name producer, premiered at
Tribeca, had a sold out theatrical run. He's
still examining that online community he was
initially fascinated by, but now with a much
more critical eye on its global impact politically
and socially. So this intense focus on systems,
on power, on hidden vulnerabilities, it takes
on this whole other layer, a really personal
weight, when you consider something Alex Winter
revealed back in 2018. Yeah, this is where his
own story really connects with the themes in
his work, especially something like showbiz kids.
In 2018, he spoke publicly about having suffered,
in his words, intense and prolonged child sexual
abuse. And this is when he was working as a young
actor. While he was acting on Broadway, yeah.
by an older man who is now deceased. That just
adds such a painful context to everything, especially
his interest in the experiences of child performers.
Absolutely. It reframes so much. He talked very
openly about the impact, the extreme PTSD for
many, many years, how it just wreaked havoc on
him. His decision to investigate those hidden
dangers within the entertainment industry, particularly
for kids, you can see it as this incredibly brave
public way of processing that trauma. And there
was that really interesting paradox he mentioned,
too, about how he coped. That's fascinating.
Right. He specifically said that starring in
the Bill and Ted movies was therapeutic for him.
Think about that. The trauma happened in the
highly professional real world of Broadway. Right.
Intense, serious theater. And the therapy, the
escape, came from playing Bill S. Preston, this
character who's just relentlessly positive, goofy,
almost aggressively simple and safe. It's like
the hyper optimism, the sheer absurdity of Bill
was a refuge, a way to heal. That iconic role
for him was deeply therapeutic. It's a really
profound link between this huge pop culture figure
and a very difficult personal history. And that
platform he built through acting, he's now using
it very directly for activism. Which brings us
right up to 2025 and some pretty bold public
stances. Yeah, taking on some very big names
and issues. Like in February 2025, he was actively
involved in promoting these national Tesla takedown
protests. Outside Tesla showrooms, what was the
specific issue there? It was framed as a direct
response to Elon Musk's political activities.
And also this group Musk was promoting called
the Department of Government Efficiency, D -O
-G -E. W -E, like Dogecoin. Exactly. That acronym
felt like a deliberate nod to the crypto meme
culture Musk loves. So the protest wasn't just
about cars. It was about Musk's specific brand
of political influence, his whole persona as
this corporate figurehead. And Winder was careful
about how he positioned himself in that, wasn't
he? Very specific. He made a point of saying,
look, I'm an avid electric vehicle owner myself.
This is an anti -EV. It's not even anti -Tesla,
the company. It's anti -Elon Musk. He called
Musk a toxic figurehead. So the goal was to pressure
Tesla to distance itself from Musk. That seemed
to be the stated aim, yeah. Using his own platform,
even his consumer choice as an EV owner, to critique
the leader at the top. And that willingness to
get involved in tricky political areas didn't
stop there in 2025. No. Later in the year, in
September, he signed on to an open pledge with
a group called Film Workers for Palestine. Okay,
what did that pledge entail? It committed the
people who signed it to not working with Israeli
film institutions that the pledge organizers
believe are complicit in genocide and apartheid
against the Palestinian people. That's a very
strong statement, especially within the film
industry. It's a really bold move. It shows he's
willing to draw professional lines based on complex
international conflicts. It really cements this
identity he's built as an engaged activist, someone
using his industry standing for political ends,
a million miles away from the slacker dude. persona,
really. It really is something, isn't it? To
trace this path, the deep dives into tech and
finance, the political protests, the personal
revelations, and then realize, oh yeah, he's
also still acting and directing commercial stuff
too. Like he's woven all these seemingly separate
threads together. Completely. And maybe the biggest
symbol of that weaving together was Bill S. Preston
coming back. After all those years of development
hell, he and Keanu Reeves finally made Bill and
Ted face the music in 2020. And the plot was
almost about his own journey in a weird way.
Kind of meta, yeah. The whole movie is about
how Bill and Ted haven't written the song yet.
The one that's supposed to unite the world. They're
dealing with middle age, family, the pressure
of that unfulfilled destiny. That was perfect.
Here's the guy who spent the last decade analyzing
the actual real world complex systems threatening
us. You know, the dark web, shady finance. And
he's playing a character still struggling to
save the world with just a rock song. It acknowledges
that saving the world is maybe a bit more complicated
than just being excellent to each other. It fits
his trajectory perfectly. And he's definitely
keeping both feet planted in both worlds. Looking
at his recent stuff, it's still that mix. 2024,
he was in that totally bonkers movie, Destroy
All Neighbors. Back to the gonzo horror comedy,
playing two parts in that one, Vlad on a public
defender, just embracing the weirdness again.
And then for 2025, he's wearing all the hats
again. Produced, directed, and starred in a feature
film called Adulthood. See? He's constantly flexing
all those muscles, directing, producing, performing.
Sometimes all on the same project. He's not choosing
one over the other. But the thing that really
feels like it closes the loop, maybe, the thing
that connects the experienced filmmaker and activist
all the way back to that disciplined kid taking
the train into Manhattan, it's the stage return.
Absolutely. Returning to Broadway, fall 2025,
with Keanu in Waiting for Godot. That's not just
any play, it's Beckett. It's pure, stark, minimalist
theater. A deep philosophical dive into waiting,
existence, meaninglessness. Talk about whiplash
again. From destroy all neighbors and criticizing
Elon Musk to Beckett. It's more than just showing
range, though. It feels like a deliberate statement,
solidifying his seriousness, maybe, returning
to that high art standard from his youth. But
now, as this globally recognized figure known
for something completely different. It's like
the ultimate synthesis. Exactly. The disciplined
performer, the determined filmmaker, the documentarian,
the activist, all coming together to tackle one
of the most profound texts about the human condition.
It ties everything together beautifully. So wrapping
up this deep dive on Alex Winter, it's just been
this incredible arc, hasn't it, from that...
Really rigorous start as a child actor through
the absolute cultural explosion of Bill and Ted.
And then strategically using that explosion,
that fame, not just to stay famous, but to pivot,
to become this serious, award -winning documentarian
digging into really complex stuff. Yeah, using
that platform now to really scrutinize these
massive global forces, anonymous digital economies,
hidden money, the power of platforms like YouTube,
even the political moves of huge figures like
Elon Musk. He turned being Bill S. Preston into...
like a tool for serious investigation. It really
messes with your assumptions. The guy forever
known as the most excellent dude who literally
fought evil robot versions of himself. He's now
the one making films that critically examine
the financial and political wiring of our entire
world. It leaves you with a pretty interesting
thought, doesn't it? What does this tell us about
pop culture fame? Can it actually be transformed
intentionally into a platform for real social
and political critique? And maybe the bigger
surprise, how often is it the people we might
write off early on, the ones labeled slackers
or goofballs because of a role they played, how
often do they turn out to be the ones paying
the closest, most critical attention to how the
world actually works underneath the surface?
Something to think about.