Icabod Crane… John Mulaney
Headless Horseman… Beck Bennett
William… Pete Davidson
Mikey Day
[Starts with a man walking into the woods in a full moon night.]
Icabod Crane: Keet it together, Icabod Crane. Nothing to be afraid of in these spooky, scary woods. [spooky noise] What? What is that? [he sees an owl] It was only an owl. Calm your nerves, Icabod.
Unknown voice: Icabod Crane.
Icabod Crane: Who’s there? Show yourself.
Unknown voice: Icabod Crane. [There’s a headless horseman] How dare you trespass in these woods on all Hallow’s eve?
Icabod Crane: My god, it’s the headless horseman. The one I heard tale of in ghastly stories.
Headless Horseman: The very same.
Icabod Crane: And it’s true what they say. You’re cursed to carry around your own severed head.
Headless Horseman: For eternity.
Icabod Crane: So, since you’re holding a detached but animated head, do you ever use it to… you know.
Headless Horseman: To what?
Icabod Crane: Do you use it? You know, like, on yourself?
Headless Horseman: What? What on earth are you talking about?
Icabod Crane: No. It’s– Okay, look. I’ve been trying to do it with myself with my regular attached head. I tried yoga and I tried stretching. I even had the town doctor remove two of my ribs.
Headless Horseman: Argh! That’s disgusting.
Icabod Crane: Oh! Says the man holding his severed head. Don’t tell me it never crossed your mind. Look how you’re holding the head. The mouth is already right there.
Headless Horseman: Honestly, I’ve never thought about it.
Icabod Crane: Well, it would have been my first thought right after, “Oh, my god. They chopped off my head”, I would have pivoted to, “Huh? Possible silver lining here.” It’s like they always say, ‘when life hands you a severed head, you put your mouth on your digus.’
Headless Horseman: Enough! You’ll have plenty of time to think such foul thoughts after I send you straight to hell.
[William walks in]
William: Icabod, I came as soon as I could.
Icabod Crane: Oh, how brave. You came to rescue me, William?
William: No. I wanted to ask the horseman some questions. You ever just roll into the ladies room?
Headless Horseman: Excuse me?
William: The head. You ever roll it under the stalls in the woman’s bathroom and be like, “Mental pictures”.
Headless Horseman: No! Of course, not. I don’t even go indoors.
William: Okay. Then you ever use your head to… you know… on yourself?
Headless Horseman: He already asked that.
Icabod Crane: I already asked that.
William: Great minds.
Icabod Crane: Hey, follow up to my thing. Do you, like most men in our era, have false removable teeth because that could feel really good if you got–
Headless Horseman: I have real teeth.
William: Ah! Bummer!
Icabod Crane: But could you tilt the head so that you can make eye contact, like, if someone wanted that, I mean.
Headless Horseman: No. I mean, yes. But why would anyone want that?
William: Personal connection.
Icabod Crane: Power, for me.
William: Hey. When your throat got cut, did it happen to the gag reflex?
Headless Horseman: Okay. Now, I’m sending you both to hell.
William: Why send us to hell when you can send yourself to heaven?
[Mikey walks in]
Mikey: Icabod, William, did you ask the horseman about–
Icabod Crane: Yes, yes. We’re like, way into it.
Mikey: Then, I have a question that’s gonna seem weird on several levels. But is the head dishwasher safe?
Headless Horseman: What are you talking about?
Mikey: I’m just curious about clean up.
Icabod Crane: No, no, I get that. But listen, it’s an open neck, right? So, he could probably just drink a glass of water after you do it. And it just like, falls out.
William: Yeah. You could probably go in through the neck too. That’s a whole new experience.
Headless Horseman: All your minds are filthy. What is going on in this town?
Icabod Crane: Well, it’s full of puritans, homie. We’re the most sexually repressed people in history.
William: Yeah. Sorry I’m obsessed with sex. This is going to shock you but my wife Goodie Chasity isn’t exactly fulfilling my needs.
Headless Horseman: Alright. I’m through with this conversation. Icabod Crane, you shall suffer my wraith– [William walks to Headless Horseman and tries to lift his head off his hand.] Hey! What are you doing? No.
[William passes the head to Icabod Crane]
Icabod Crane: Alright. Let’s just say things are coming to a-head [pun].
Male voice: And so, the legend of sleepy hollow was born. They say if you walk the woods today, you can sill hear the ghostly cries of the horseman’s head yelling, “Come on guys! I need a break!” And then, “Hey, hey! The ears are off-limits!” Happy all hallows eve, from all of us at NBC, but mainly Lorne who wrote this sketch.