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The Headless Horseman heads on out, expanding his turf beyond Walt Disney World for the 2013 Halloween season

You think — what with all the attention that he’s been
getting lately — you’d think that the Headless Horseman would have a bigger
head. If he had a head, I mean.


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To explain: Until relatively recently, if you were looking for a cinematic
representation of this particular Washington Irving tale, you’d basically have
no choice but to default to Disney’s 1949 package feature, “The Adventures
of Ichabod and Mr. Toad

.” Where — thanks to Mary Blair‘s art direction
and Woolie Reitherman‘s muscular animation — that particular version of
the  Headless Horseman made a very big
impression on moviegoers.

And Walt … He knew that. But Disney could then never quite
figure out how to capitalize on the popularity on this particular character.
During the early development phase of The Haunted Mansion for Disneyland
Park
(back when this attraction was
still supposed to be a walk-thru), the Imagineers toyed with the idea of having
this experience climax with the arrival of the Headless Horseman. With the idea
being that the Wizards of WED could — through the judicious use of stereo
speaker placement as well as some projected effects — give the impression that
the Headless Horseman atop his fiery steed had just ridden up and was now lurking
right outside of the mansion. Which was why — especially if you were a theme
park visitor who liked your head just the way it was (i.e., still attached to
your neck) — it would probably be a good time to vacate The Haunted Mansion.

But once the Mansion got re-imagined as a ride-thru rather
than a walk-thru, that version of this attraction’s finale got tossed aside
like last year’s jack-o-lantern. Which isn’t to say that the Imagineers had
entirely given up on the idea of bring Ichabod Crane & his headless nemesis
into the Disney theme parks. Far from it, in fact.


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You see, in the late 1960s, rather than make the three dark
rides that were supposed to be built for the Fantasyland section of WDW‘s Magic
Kingdom
just be carbon copies of the three dark rides that were already in
Disneyland Park’s Fantasyland section, WDI wanted to do something similar but
different. So — instead of “Snow White’s Scary Adventures” — the
Imagineers wanted to do a dark ride themed around “Sleeping Beauty
.”
Which was to have featured some pretty scary encounters with that Mistress of
All Evil, Maleficent.

And in the place of “Peter Pan’s Flight” … Well,
WDI had long wanted to do a “Mary Poppins
” – themed attraction where
Guests would climb aboard those magical merry-go-round horses and then go
bounding off into that colorful English countryside that Bert had drawn for his
chalk sidewalk drawing. (Just so you know: There was an alternate attraction
proposed for this part of Fantasyland. One that — it was felt — would be a
far better fit for this medieval-themed area 
of that WDW theme park. And that was the “Wizards Duel” dark
ride. Where Guests would have found themselves right in the middle of that manic
scene from “The Sword in the Stone
” where Merlin & Mad Madam Mim
are doing battle. And you traveled from room to room in this ride, you’d
narrowly avoided being hit by magic spells yourself.)

And — finally — in the place of “Mr. Toad’s Wild Ride,” the
Imagineers wanted to do a “Legend of Sleepy Hollow” ride. Where
Guests were to have first boarded these giant, hollowed-out jack-o-lanterns
that featured a central steering wheel just like the ones inside of the giant
teacups found at the Mad Tea Party ride. Which meant that — as your
jack-o-lantern moved through the dark & scary forest right outside of Tarrytown,
NY (i.e., where Washington Irving set the
story of Ichabod Crane) — you’d then be able to spin this super-sized pumpkin
around. Which meant that you then had the option of steering your ride vehicle
so that you always look directly at the Headless Horseman when he suddenly
appeared OR spin your jack-o-lantern in the opposite direction. So that you
could deliberately avoid being face-to-face with that headless fiend.


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These three / four dark rides all sound like great additions
to WDW’s Fantasyland, right? So why were they never built. Blame Roy O. Disney.
Who — when the proposed construction costs of the Walt Disney World Resort
began to balloon from the originally projected $100 million to a budget-busting
$400 million — began actively looking for ways that the Company could contain
costs in Central Florida. And when Roy O. was told about
these three new dark rides that were in the works for the Fantasyland section
of WDW’s Magic Kingdom
theme park, he reportedly said “Why are we reinventing the wheel? We
already have three rides in Southern California that
people love. Let’s try and save some money here by replicating those dark rides
and then sending them to Central Florida.”

Which isn’t to say that the Imagineers were willing to give up entirely on
their dream of  bringing some of
Washington Irving’s world to Walt Disney World. Which is why they then added
the Sleepy Hollow Inn to that theme park’s Liberty
Square section. And if you knew anything about
Sunnyside (i.e., the old Dutch stone house that Irving bought in Tarrytown, NY
and then greatly expanded), you’d then realized that WDI has
“borrowed” the unique roof shape from Washington’s home and then made
a key feature of this quick service restaurant.

But just because the Headless Horseman couldn’t find a permanent home
in WDW’s Magic Kingdom
didn’t then mean that this Disney Villain couldn’t then find a seasonal excuse to pop up on property. For a number of years now, the Horseman has galloped down Main Street, U.S.A., just ahead of the Mickey’s Boo-to-You Halloween Parade at every Mickey’s Not-So-Scary Halloween Party at the Magic Kingdom. And for a while there, he’d also make his presence known to
those who dared to venture into that dank cypress forest where Disney’s Fort
Wilderness Resort and Campground
is located. Where the Headless Horseman would then come roaring up out
of the darkness aboard his fiery steed and frighten those poor souls who’d
been brave enough to sign up for a Haunted Hayride.


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But sadly, due to some contract dispute and/or insurance-related issues, Fort
Wilderness’ Haunted Hayrides &
carriages have been discounted. And what’s become of the Headless Horseman? Well,
on the heels of Tim Burton’s 1999 film, “Sleepy Hollow
,” the Horseman
successfully made the transition from being just an animated menace to the
realm of live-action horror film star.

And just over the past six weeks, the Headless Horseman has
expanded his turf. Shifting from the big screen to the small screen as the central
villain of “Sleepy Hollow.” Which is this new drama for Fox that’s
already proven to be so popular with viewers that — although we’re only five
episodes into this “Sleepy Hollow” ‘s first season — network
executives have already renewed this show for Season Two.

And meanwhile over at ABC Family, the Smurfs have just
managed to put their own tried-and-blue … er … tried-and-true spin on this
Washington Irving tale from 1820. And as you can see by this clip from
The Smurfs: The Legend of Smurfy Hollow
,” the Headless Horseman is
still a force to be reckoned with.

[View:http://www.youtube.com/watch?v=JlT4UC5IeiQ]

And speaking of which … If you happened to be passing
through New York State
over the next few days, you might want to consider dropping by the
really-for-real Sleepy Hollow. Which is where — now through November 11th —
there are all sorts of Headless Horseman-related activities currently going on.
Everything from the Great Jack O’Lantern Blaze (where over 4,000 hand-carved
pumpkins illuminated the mysterious woods & buildings found at Van
Cortlandt Manor
) to Horseman’s Hollow (which is where — for 13 nights only —
historic Philipsburg Manor gets transformed into this terrifying landscape filled
with witches, ghosts and undead soldiers). There’s even a Haunted Hayride —
where just like on the old Fort Wilderness
version — Guests find themselves being pursued by the Headless Horseman
himself as they roll through the woods.

Which is why — given how successful the Headless Horseman
has been in 2013, how this creepy character’s career has been exploding lately
… Well, who knew that you didn’t need a head to get ahead these days?

Jim Hill

Jim Hill is an entertainment writer who has specialized in covering The Walt Disney Company for nearly 40 years now. Over that time, he has interviewed hundreds of animators, actors, and Imagineers -- many of whom have shared behind-the-scenes stories with Mr. Hill about how the Mouse House really works. In addition to the 4000+ articles Jim has written for the Web, he also co-hosts a trio of popular podcasts: “Disney Dish with Len Testa,” “Fine Tooning with Drew Taylor” and “Marvel US Disney with Aaron Adams.” Mr. Hill makes his home in Southern New Hampshire with his lovely wife Nancy and two obnoxious cats, Ginger & Betty.

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