Welcome back to the Deep Dive. You've given us
the sources and we're here to pull out the most
fascinating, need -to -know stuff. That's the
plan. Today, we're diving deep into the career
of Douglas Steven Benson, comedian, actor, host.
It's quite a ride. It really is. We're looking
at this arc, you know, from being an extra on
classic movie sets through reality TV and then
really hitting his stride in the kind of early
days of podcasting and weed culture commentary.
Exactly. And this isn't just about listing credits.
It's about a whole brand, right? A career built
on, yeah, the comedy, observational, satire,
sarcasm, all that. But it's fundamentally linked
to his very public, very open advocacy for recreational
drug use. That's key. And what's really interesting
is how he used that persona, that specific angle,
to become this central figure in comedy podcasts
when they were still pretty niche. Yeah, pioneer
almost. Totally. And then translating that super
specific brand to TV, even ending up with a legally
binding court show. It's kind of wild when you
lay it all out. A real study in mastering a niche.
So our mission for you, listening in, is pretty
straightforward. We want to synthesize all this
diverse work, but, you know, go deeper than just
the surface level. We're connecting the dots.
How do you go from being a face in the background
in, like, 80s movies to launching multiple hit
shows focused on very specific things and dominating
panel shows? It's the details. Exactly. We're
zeroing in on the specific projects, the strategic
moves, the little details that make his whole
body of work so unique in comedy. Okay, let's
do it. Okay, let's untap. All right, so the basics.
Douglas Stephen Benton, born in San Diego, California,
July 2, 1962. So he's 63 now. Okay. And the family
background. It's kind of interesting given where
he ended up. His mom was a pharmacy clerk. His
dad was an English teacher who later went into
sales. So pretty grounded middle class background.
Very much. Southern California upbringing, which
makes his later sort of counterculture persona
stand out more. And even back in high school,
Grossmont High, he was already creating stuff,
right? Not just acting. Yeah, that's a great
point. He was in the drama department. Sure,
that's common. But the thing that jumps out is
him making these like eight millimeter action
and thriller short films. With a friend. Wow.
OK, so hands on filmmaking. Right. Junior, senior
year. He wasn't just performing. He was thinking
about structure, storytelling, the whole cinematic
process. Even then. Which maybe explains his
later obsession with movie details and rules.
I think it connects directly. It shows he came
into the entertainment world with not just a
performer's view, but also thinking about like
the mechanics of media. How things are put together.
We totally see that later with his podcast games.
And speaking of mechanics, there was that personal
health detail. Something about his eyes. Yeah,
this is interesting. As a kid, he apparently
struggled with vertigo and had poor depth perception.
So it was because his eyes are close set. Huh.
So literally seeing the world a bit differently.
Possibly, yeah. Having to navigate with maybe
a slightly skewed or flatter... visual field.
You wonder, does that difficulty with spatial
stuff maybe push someone towards more analytical,
structured thinking? Like creating really complex
trivia games instead of relying on, say, physical
comedy. Could be. It might partly explain why
his biggest successes are built around these
intricate, detail oriented. Game structures.
It definitely leans into the intellectual side
of things. So after Grismont College, he does
the classic thing, Moose to L .A. to act. Yep,
the 1980s Hollywood hustle. Taking those stand
-in jobs, extra work, trying to make rent while
looking for actual roles. And those gigs put
him right in the middle of some iconic films.
Absolutely. He worked as a stand -in a lot, but
also popped up as an extra or in tiny parts in
huge movies from that era. We're talking Blade
Runner. Wow. Fast Times at Ridgemont High. Right.
About last night. This period is crucial. It's
where he soaked up all that film trivia, learned
about production, credits. The stuff that literally
becomes the basis for Doug Love's movies. Exactly.
That deep, almost obsessive knowledge of how
movies are made and who's in them. And the weirdest
detail from that time. The Disney thing. Oh,
yeah. Captain EO. 1986. He was apparently a backup
dancer in this huge 3D Michael Jackson sci -fi
musical attraction at Disneyland. Directed by
Coppola. That's wild. It really is. From the
grit of Blade Runner to sparkly MJ choreography
in 3D, it just shows the sheer variety of gigs
you had to take to survive in Hollywood back
then. Total adaptability. But the acting wasn't
the thing that clicked career wise. It was stand
up. Right. And kind of by accident. Yeah. The
stand up origin story is classic. Age 22. Wasn't
like a burning desire apparently. He and two
buddies dared each other to try it. And the friends
bailed. Pretty much. One didn't show the other
signed up too late. But Benson actually did it.
Got on stage. Did what he called three minutes
of whatever. And people laughed. Yeah. He said
people actually laughed. And that's often all
it takes. Right. That little bit of validation
to turn you from someone watching comedy to someone
doing it. But the whole stoner comic thing, that
wasn't immediate. That's the key timeline thing
people miss. Crucial point. He was doing stand
-up for like six years before that persona really
formed. He became a dedicated stoner, as he puts
it later, around age 28. After smoking with other
comics? Yeah, apparently after a week of hanging
out and smoking pot after gigs with Brian Posen
and Greg Proops. So it wasn't like some teenage
discovery. It was an adult choice. Right. And
he later folded that lifestyle choice into his
comedy. It wasn't the reason he started comedy.
Exactly. It fit his style, that observational
kind of analytical approach. And then he just
leaned into it hard, turned a personal habit
into a whole media identity. So while that identity
was forming, he was still grinding away, getting
TV spots. Those late 80s, early 90s appearances
on Comedy Central shows like The A -List, Two
Drink Minimum, Building Credits. And The Writing
Work. Important, too. Wrote for that MTV game
show Trash to 94. Again, you see the interest
in game structure, learning how to burn those
mechanics. Foreshadowing. Totally. And he was
in Joel Hodgson's pilot, The TV Wheel, after
MST3K. Part of that alt -comedy scene. And all
this kind of comes together with the marijuana
lugs, right? That seems like a big step. Huge
step. Co -creating and performing that stage
show with Arch Barker and Tony Kamen. It ran
for a long time, toured. That really cemented
his public connection between comedy and cannabis.
It set the stage perfectly for what came next.
Okay, so this is where things really explode
for him, right? The move into podcasting. This
feels like the turning point. Absolutely. Around
2006, he launches I Love Movies with Doug Benson,
quickly becomes Doug Loves Movies, DLM. And back
in 2006, podcasting was... Different, much more
of a Wild West. Oh, yeah. Very niche. And what
he did was smart recording it live, usually at
UCD in L .A. That gave it an energy, that live
comedy club feel that a lot of early, you know,
recorded in a closet podcasts didn't have. The
format seems simple on the surface. Talk about
movies, have comedians on. Right. But the execution,
the structure, that's where the genius is and
the absolute core of it. The thing that's driven
it for, what, nearly two decades now? The Leonard
Moulton game. Okay, break this down for anyone
who hasn't heard it. It's more complicated than
it sounds. Definitely. People call it Name That
Tune With Movies, which is kind of right. But
way nerdier. Way nerdier. Needs super deep film
knowledge. So, Benson reads bits from a movie
review, usually from Leonard Moulton's old guides.
The guests then have to wager. Wager on what?
On how many names. Read from the bottom of the
cast list upwards. It'll take them to guess.
the movie. Okay, so the lower the bid, the harder
it is. Exactly. If you bid, say, five names,
he reads the fifth to last actor credited. Usually,
as someone pretty obscure, if you bid one name,
you're banking on recognizing the movie just
from the very last credited actor, often like
Man Hashtag 2 or something. It rewards that insane
recall for character actors and bit parts, the
kind of knowledge he probably picked up being
a stand -in. Precisely. It taps into that deep
cinephile knowledge base and it creates these
like legendary moments on the show. Like the
negative names thing. That sounds impossible.
Right. Sean Sakame, a fan who won an auction
to be on, won the Tournament of Champions in
2013. Then to qualify the next year, he guessed
Titanic in negative names, meaning he guessed
it correctly just from the review before Benson
even read any names from the cast list. Just
pure deduction and confidence shows the level
of obsession the game inspires. And there's the
big annual championship, the Christmas special.
Yeah, the 12 Guests of Christmas, huge two -hour
elimination -style game with a dozen or more
comics. It's like the DLM Super Bowl. And there
are rivalries, recurring champs. Oh, yeah. Scott
Aukerman won the first one, then won again years
later in 2015. Graham Elwood had a dominant run
for a couple years. Rikki Lindholm had a big
win over Jimmy Pardo in 2014. It creates this
whole meta -narrative within the L .A. comedy
podcast world. But DLM isn't just the Maltin
game. He invented a ton of other segments, right?
That speaks to his creativity, too. Absolutely.
The sheer number and variety of games show his
knack for structure and, frankly, absurdity.
We don't need to list all 20, but some are just
brilliant concepts. Like Lincoln or Bane. Perfect
example. He reads a quote. You have to say if
it was Abraham Lincoln or Bane from The Dark
Knight Rises. Because they both have that kind
of slow, formal delivery. Exactly. The juxtaposition
is hilarious. Or now Buscemi, now you don't.
Which is. It's like the shell game, but with
pictures of Steve Buscemi because, you know,
Buscemi's in everything. It's a running commentary
on character actors. So it's trivia mixed with
meta commentary. Totally. And doing lines with
Mark Wahlberg, just quoting Wahlberg movie lines.
ABCD's nuts. He's constantly finding ways to
twist movie trivia into reputable, funny formats.
And the closing catchphrase saga is fascinating,
too. The Willem Dafoe thing. Oh, man. Yeah. For
years, he ended every show with, as always, Willem
Dafoe is a shithead. Which was pure satire, right?
Like, Dafoe is so respected, it's absurd to attack
him. That was the joke. Benson thought it was
the most random, illogical thing to say. But
a lot of listeners didn't get the satire at all.
They thought he genuinely hated Willem Dafoe.
Yeah. He got confused emails, people asking what
Dafoe ever did to him. The joke just didn't land
universally. So he had to explain it over and
over. Right. Eventually, he kind of retired it,
let Dafoe rest. But the concept lived on for
a while until 2019. The runner -up in the Malton
game got to name their own shithead as a consolation
prize. A little moment of catharsis for losing.
Pretty much. But that ended. Now the closing
is positive energy. Which is a tribute. Yeah,
a direct tribute to his friend, the comedian
Brody Stevens, who passed away and used that
phrase a lot. So it shifted from absurdist satire
to something more genuinely causative. It shows
evolution. Yeah. And beyond his own show, he
became like podcasting royalty, guesting everywhere.
Oh, absolutely. Comedy bang. Bang. WTF, Joe Rogan,
nerdist. If you had a comedy podcast, you wanted
Benson on. He was reliable, quick, knowledgeable,
brought that energy. He became a connector in
that whole scene. The cannabis -centric media,
documentaries, talk shows, and legal rulings.
Okay, so DLM gives him this huge dedicated audience.
And that platform lets him really dive into the
media that fully embraces the cannabis brand.
Starting with Super Jaime. 2007 release, right?
The title obviously playing on Supersize Me.
Exactly. Morgan Spurlock ate McDonald's for 30
days. Benson's experiment was 30 days no marijuana,
then 30 days smoking as much as possible. A pretty
bold public experiment. Totally. Part comedy
stunt, part personal advocacy. And the results,
at least as presented in the film. Minimal negative
effects, right? Yeah. Based on his tests, cognitive
checks, general health monitored in the doc,
the conclusion was that the heavy use period
didn't really harm him significantly, which was,
you know, a big statement against the prevailing
anti -drug messaging at the time. It gave the
pro -legalization side a kind of funny, relatable
data point, even if it was just one guy. Right.
Look, I did this, professionally documented it,
and I'm fine. It resonated. But things got messy
after the film's success. There was a lawsuit.
Yeah, that happens. The other producers wanted
to release a sequel, Super High Me Redux, using
leftover footage. Benson sued them around 2014,
2015 to stop it. So clearly some friction there
about control and maybe how the original is being
exploited later. Then came the talk show, Getting
Dug With High. This feels like the ultimate expression
of his brand at the time. For sure. Ran from
2013 to 2019. weekly show on YouTube, streamed
live, usually Wednesdays at a very specific time.
4 .15 p .m. Pacific. Yep. Setting up the main
event. The 4 .20 smoke session. Exactly. The
core ritual. He'd have guests on, huge names,
Snoop Dogg, Sarah Silverman, Cheech Marin, Jack
Black, tons of comics, and they'd all light up
together right at 4 .20 PST during the live stream.
And talk. Yeah, talk about whatever. Usually
cannabis -related comedy movies. Very relaxed,
obviously. How did they handle the live audience
shows? Couldn't exactly hotbox the venue. Good
question. They adapted. Often used vaporizers,
with guests inhaling from those big bags of vapor.
It kept the ritual intact, visually, without
violating venue rules or smoking laws. A smart
workaround. And the ending. The magic trick.
Always. Every single show, no matter who the
guest was or how high they were, ended with Benson
making them watch a magic trick. Just pure, delightful
Benson weirdness. Totally. A signature, absurd
little flourish. Okay, but the absolute weirdest,
most ambitious project has to be the High Court.
2017, Comedy Central. This one is fascinating.
It's a court show. Yeah. Like Judge Judy or People's
Court, standard format. The judge is Doug Benson,
and he's high, openly. Yes, that's the entire
premise. He's the judge. ruling on cases while
admittedly under the influence of cannabis during
the taping. Now, the crucial detail here, the
thing that makes it more than just a sketch,
the cases were real. Absolutely real. These were
actual small claims disputes. And his rulings
were legally binding. Yes. That's the mind -bending
part. It worked like binding arbitration. The
people bringing their cases, signed contracts,
agreeing to accept Judge Doug's decision, whatever
it was, high or not. So real legal consequences
decided by a comedian who's openly stoned on
camera. Pretty much sums it up. Yeah. And the
show played into it. There'd be segments where
Judge Doug and the bailiff would retire to chambers,
which meant they'd go smoke weed while deliberating
the case. It's performance art meets actual legal
process. It's kind of brilliant commentary, actually.
It really is. Pushing the boundaries of comedy,
reality TV and the justice system all at once.
And quickly. The Benson interruption. That started
live, too. Yeah, long -running live show where
he'd literally interrupt other comedians during
their sets. Very confrontational, funny stuff.
Got a TV version on Comedy Central for a bit.
One season in 2010. But then, naturally, he spun
it off into a podcast in 2011. Audio only, longer,
unedited sets and chats. Again, adapting a successful
live concept for the podcast medium he knew so
well, Consistent Pattern. So we've seen the podcast
The Weed Shows. But we also need to talk about
his sheer output of traditional stand -up. He's
released, what, 10 comedy albums? At least 10,
yeah. Starting with Professional Humorudian back
in 2008. And he has this specific goal with the
albums, right? The timing. Yeah, it's very deliberate
branding. He aims to record a new album every
April 20th. Naturally. Naturally. For a release
later that summer, he wants to keep that streak
going for as long as possible. It's smart. It
ties his stand -up directly to the 420 date,
reinforces the brand, creates anticipation. He
becomes the official comedic chronicler of that
date, in a way. And the titles reflect the brand,
too. Potty Mouth, Smug Life. Smug Life is a great
one. Very self -aware of his stage persona. Then
Gateway Doug. Gateway Doug 2. Forced fun and
promotional tool. He's definitely in on the joke
about his own marketing. Absolutely. He knows
the game. But beyond his own albums... He was
also making waves in mainstream TV competitions
and panel shows. Right, last comic standing in
2007. He was actually a contestant. Yeah, fifth
season. And he did really well. Got significant
exposure. Made it pretty deep. Finished sixth
overall, I think. So his niche comedy style could
play to a broader audience. It showed it. It
could translate, yeah. And he was a regular on
VH1's Best Week Ever for years doing that pop
culture commentary thing. The dry, sarcastic
take. Exactly. Plus that G4 special in 2009,
The High Road, following him and Graham Elwood
on tour. More proof people were interested in
him as a personality, not just a performer. But
his biggest competitive stage was probably at
midnight, right? The Comedy Central show. Oh,
he owned that show. It ran from 2013 to 2017,
all about rapid fire jokes based on Internet
stuff. Perfectly suited for his quick wit. And
his record was insane. Unmatched. He holds the
record for both the most appearances and the
most wins on the show. Like by a lot. He was
the undisputed champ. To the point where they
basically built a week around him. Yeah. January
2016, they did the Benson Bowl, a whole week
of competition, and lots of the games were specifically
tweaked to have weed themes. It showed how central
his persona was, even to that fast -paced format.
The show literally adapted to him. And all this
time, he's still popping up in acting roles occasionally.
Kept his hand in, yeah. Small parts, but on huge
shows. Mr. Show, Friends. Friends, really? Yep.
Curb Your Enthusiasm, How I Met Your Mother,
Sarah Silverman Program. Yes, dear. just steadily
working, showing up in the background of major
sitcoms. And more recently. Trailer Park Boys,
you're the worst, did voice work on Bob's Burgers.
And the voice of Bane in the Lego movie. Right,
the Lego Batman movie in 2017. Full circle back
to movies, using that distinctive voice for a
major villain parody. Kind of perfect. Okay,
so we've tracked this huge... successful, very
specific career. But if we're looking at the
whole picture, we absolutely have to talk about
the red eye incident. March 2009. This feels
like a major bump in the road. It's more than
a bump. A really stark example of how comedy,
especially satire, and that kind of deliberately
ignorant persona can just crash headlong into
real world tragedy and politics. With serious
consequences. So the setup. He's on Greg Gutfeld's
show, Red Eye, on Fox News. They're talking about
Canada's military. Yes, specifically a comment
by a Canadian general, Andrew Leslie, who'd suggested
the Canadian forces might need a year -long break
after their mission in Afghanistan ended in 2011.
And Gutfeld started with jokes about them doing
yoga and painting. Standard stuff. Playing on
stereotypes. But then Benson chimed in. And his
comments were... First, I didn't even know they
were in the war. Then... I thought, that's where
you go if you don't want to fight. Go chill in
Canada. Oof. Okay. Playing dumb, but... Playing
dumb at the worst possible moment. The timing
was just catastrophic. Why? What had just happened?
The segment aired, or at least hit YouTube, just
three days after four Canadian soldiers had been
killed in Afghanistan. Oh, wow. Okay. That changes
everything. Completely. It transforms the joke
from maybe slightly lazy satire into something
deeply disrespectful, appearing to mock a nation
actively grieving its soldiers. And Canada's
role wasn't minor, right? They were heavily involved.
Critically involved. Yeah. They were leading
the NATO mission in Kandahar province, the Taliban's
heartland. Sources say Kandahar had some of the
highest casualty rates for coalition forces.
So for Benson to say, I didn't even know they
were in the war. looked like profound, willful
ignorance of real sacrifice. Exactly. And the
reaction in Canada was furious, immediate. Official
reaction, too. Oh, yeah. The Canadian defense
minister, Peter McKay, personally demanded an
apology from Fox News, called the comments despicable,
hurtful, and ignorant. This wasn't just online
chatter. It was a diplomatic incident. And it
hit Benson directly. Canceled shows. Yep. He
had gigs scheduled in Edmonton, Canada. The club
owner canceled them, citing threats of Bodily
injury against Benson. Real serious backlash.
So how did Benson respond? To his credit, he
seemed to grasp the severity pretty quickly.
Yeah. He went on Canadian TV, CTV News, and gave
a direct, seemingly sincere apology. What did
he say? Admitted he was ignorant about the situation
in Afghanistan. Said the timing was completely
out of line. He didn't try to hide behind it.
It was just a joke. He owned it. Seemed to. Said
things like, I honestly said things in retrospect
I completely regret. and he vowed he'd never
appear on Red Eye again. It was a full mea culpa,
a real wake -up call about the limits of edgy
comedy when it bumps up against raw national
pain. Hashtag have DJ Z -Sive. Outro. Okay, so
let's try and wrap this up. Looking back at this
whole deep dive on Doug Benson, what are the
big takeaways? For me, it's that incredible consistency,
the prolific output, 10 albums, the super long
-running podcast, the cannabis shows, all very
focused, very structured. Definitely the focus.
And his ability to fuse that pop culture knowledge
with the personal advocacy, making his unique
selling proposition. He really rode the wave
of new media. Podcasts, especially. Yeah, he
mastered that space. But the career also shows
maybe the power of finding that very specific
niche, right? Absolutely. Marrying comedy with
a lifestyle choice built him this incredibly
dedicated fan base. But as the red eye thing
showed, there are real world lines. Satire has
boundaries, especially when it touches on things
like national sacrifice or tragedy. You can't
always play dumb. It highlights the responsibility
that comes with having that platform, even if
your platform is built on being irreverent. Right.
Which leads us to that final thought, something
for you, the listener, to chew on. It ties back
to the high court. The legally binding rulings
from the high judge. Exactly. Considering he
actually had the power to make real legally binding
decisions in that community context. What responsibility
does a comedian take on when their persona, their
act, crosses over into roles usually reserved
for serious authority figures? Even if the whole
thing is presented as comedy, does the context
erase the responsibility that comes with the
power? Yeah. What stands out to you about that
blurring of lines? The comedian as judge. Literally.
Where does the performance end and the real world
impact begin? Something to think about. Definitely.
How media keeps playing with those boundaries
between entertainment and authority. Always evolving.
We'll catch you next time for another deep dive.