Headless Horseman Puns
1. The Headless Horseman got a job delivering pizzas, but he kept getting lost. He has no sense of direction!
2. Did you hear about the new Headless Horseman video game? It’s rated E for Everyone because it contains no graphic decapitation.
3. I ran into the Headless Horseman at the department store and asked what he was looking for. He said, “I need ahead of myself for Halloween.”
4. The Headless Horseman got pulled over for speeding. The cop asked, “Do you realize how fast you were going?” The Horseman replied, “I didn’t see any signs.”
5. Why does the Headless Horseman ride so quickly through Sleepy Hollow? He’s just trying to get a head!
6. The Headless Horseman bought a parrot. It sits on his shoulder and does the talking for him.
7. I saw the Headless Horseman at the gym. His workout routine is insane – one minute he’s lifting weights and the next he’s playing basketball. He’s all over the place!
8. The Headless Horseman entered a 5k race, but he got disqualified for cutting off the other runners.
9. Why did the Headless Horseman cross the road? To get to the body shop!
10. I asked the Headless Horseman how he sleeps at night. He said, “With my eyes closed of corpse!”
11. The Headless Horseman tried to enter a haunted house but they said no costumes allowed.
12. The Headless Horseman went to the doctor for a check-up. The doctor said, “Let me know if anything pops up.”
Headless Horseman One-Liners
13. The Headless Horseman’s neck workout routine is to die for.
14. I’m stumped trying to think of a gift for the Headless Horseman.
15. The Headless Horseman doesn’t let anything get under his skin.
16. The Headless Horseman charges into battle without hesitation.
17. Don’t lose your head trying to outrun the Headless Horseman.
18. The Headless Horseman has an axe to grind.
19. Being unable to eat or speak are the Headless Horseman’s pet peeves.
20. The Headless Horseman keeps a spare head in his saddle bag.
21. The Headless Horseman heads off trouble whenever he can.
22. Even without a head, the Headless Horseman has unbridled spirit.
Best Headless Horseman Jokes
23. The Headless Horseman walked into a bar and ordered a beer. The bartender said, “Sorry, I can’t serve you. You’re obviously too intoxicated already.”
24. Ichabod Crane decided to dress up as the Headless Horseman for Halloween. He immediately regretted his decision when the real Headless Horseman showed up and shouted, “Hey, nice costume! Let’s go prank some people together.”
25. The Headless Horseman was feeling depressed, so he visited a therapist. The therapist said, “It’s clear you have some issues you’re not dealing with.”
26. The Headless Horseman applied for a job at the Sleepy Hollow Advice Column. They told him he wasn’t qualified because he didn’t have a head for giving advice.
27. The Headless Horseman was arrested for stealing hats. The police knew it was him because he fit the description of being headless.
28. The Headless Horseman went on a blind date. It went terribly because he kept talking about himself but never actually faced her.
29. The Headless Horseman decided to take up yoga to improve his focus. After his first class, he was feeling centered and refreshed.
30. The Headless Horseman was nervous about his driver’s test. But he easily passed since parallel parking is no problem when you can rotate your head 360 degrees.
31. The Headless Horseman was bored so he decided to enter a pumpkin carving contest. He carved an excellent likeness of himself, but was disqualified for using real human parts.
32. The Headless Horseman tried to sign up for Instagram but kept getting error messages. Turns out you need to upload a photo of your face.
33. The Headless Horseman went on Shark Tank to pitch a revolutionary new pillow that attaches right to your neck stump. The sharks tore his idea to shreds.
34. The Headless Horseman doesn’t understand why everyone freaks out when he shows up. He’s just trying to get a head in life.
35. The Headless Horseman was excited for Halloween this year. He hoped it would help him meet chicks who are into decapitation.
36. The Headless Horseman decided to go back to school to become a dentist. That way he could offer discounted rates since he doesn’t need to buy any equipment.
37. The Headless Horseman’s New Year’s resolution was to gain some self-confidence. It’s hard not having a head to hold high.
38. For Christmas, the Headless Horseman gifted Ichabod Crane a vintage turtle neck sweater. Ichabod did not appreciate the gesture.
39. The Headless Horseman always Requested extra pillows when staying at a hotel. He piles them on top of each other to sleep more comfortably.
40. The Headless Horseman prepared for months to run a marathon. But on race day, he forgot to bring his energy gels and hit the wall hard.
41. One night the Headless Horseman went bowling with some friends. He got frustrated because the ball kept going straight into the gutter.
42. The Headless Horseman bought a parakeet to keep him company. But it was a poor listener and kept talking over him.
43. For his birthday, the Headless Horseman wanted to go to a concert. Unfortunately, the ticket seller wouldn’t let him in without ID matching the name on the ticket.
44. The Headless Horseman decided to go back to school to become a lawyer. He was a natural because he was already well-versed in corpus juris.
45. To improve his posture, the Headless Horseman started taking yoga classes. But he could never quite nail the correct headstand pose.
46. The Headless Horseman loves photography as a hobby. But he can never manage to stay completely still and centered for self-portraits.
47. Every year the Headless Horseman carves an amazing jack-o-lantern likeness of himself. This year he hopes to finally win the blue ribbon at the Sleepy Hollow Pumpkin Festival.
48. The Headless Horseman always rode his horse at top speed through the forest. One day he crashed into a tree and had to take the horse’s reins to steer clear of branches.
49. The Headless Horseman decided to start baking cakes to earn some extra cash. But he found decorating them with fancy piping nearly impossible without depth perception.
50. For his day job, the Headless Horseman worked as a telemarketer. He was the top sales rep because his intimidating voice made people too scared to hang up.
51. The Headless Horseman loves country music concerts. But he gets annoyed when people behind him sing along badly or wear large hats that block his view.
52. Every year for Thanksgiving, the Headless Horseman hosts a big dinner party. He’s in charge of the turkey, which he expertly carves despite his limitation.
53. The Headless Horseman decided to try speed dating to see if sparks would fly with someone new. But the women were unnerved when he kept mixed up their names and backgrounds.
54. The Headless Horseman tried to make some extra money by driving for a rideshare app. But he kept getting poor ratings and complaints from passengers.
55. The Headless Horseman loves going camping and fishing in the great outdoors. He sees it as a nice escape from the chaos of his headless life.
56. To unwind at the end of a long day, the Headless Horseman likes to put on some music and savor a warm drink by the fireplace. It’s the simple pleasures that mean the most.
57. Every year for Christmas, the Headless Horseman donates gifts to less fortunate children in Sleepy Hollow. Though headless, he has a heart of gold.
58. The Headless Horseman decided to try online dating to expand his romantic prospects. But he struggled to come up with a clever bio that accurately captured his essence.
59. The Headless Horseman always declines party invitations on October 31st. He prefers to stay home handing out candy to trick-or-treaters.
60. For exercise, the Headless Horseman enjoys long solitary rides through the countryside. The fresh evening air and quiet time to think feel wonderful.