20 Funny Roasts For Someone With a Square Head

Someone is a square head if they’re not so smart or stupid. Yet, it is possible to have a head literally shaped like a square. 

And that’s where this roast comes in. 

You know the custom here at RoastHow, we roast any and everyone. In this article, the target is someone with a square head. 

Just what funny roasts can you use for someone with a head shaped like a box complete with all four angles? 

We got you. 

Read our 20 funny roasts, find that buddy with a square head and roast away. 

Table of Contents

20 Funny Roasts for Someone With a Square Head

1. What’s a square head’s best alcoholic drink? Root beer.

If you are familiar with puns and wordplay, you already know where this roast is headed. Root beer reminds you of square roots, doesn’t it? 

It is only natural that a square headed person drinks root beer. It’s an affinity of sorts. A kindred spirit thing. 

We have nothing against root beer, please. We just know, mathematically speaking, this beer is squared enough to please a square shaped head. 

  • Does Dennis drink Bud Light?

No, root beer is his thing. 

  • What kind of beer are we having?

Root beer, please, for the square head among us! 

2. How does a square-headed person greet their friends? With a “cornered” smile!

Another pun for your delight! Squares have corners. Are they 90 degrees accurate? No one’s measuring because it doesn’t matter. 

The wordplay is on the word corner. It ties in well with the idea that squares have corners too. Which is why the person offers a slanting smile. 

  • Why’s Dennis smiling in that cornered way? 

It has something to do with his square head. 

  • Can he stop giving me that cornered smile?

No, he can’t. Not with that square head. 

3. What do you call a square-headed person at a roundtable discussion? The odd corner out!

This funny roast juxtaposes the idea of a square with a circle. Roundtables aren’t supposed to be a literal thing but for this roast, they are. 

Especially since the head in question is literally square. The roast further gets interesting: we have the odd corner out, instead of the odd one out

Note the wordplay here when using this roast. 

  • James is the odd corner out at this meeting. 


Because he’s got a square head. 

  • We have a square head at a round table meeting. 

He’s going to be the odd corner out. 

4. Why did the square-headed person never get lost? Because they always knew which way was “square”!

Directions are measured in square roots in the universe of a person with a square head, according to this roast. 

In this person’s world, all the direction on the compass is perceived in squares. This is not supposed to make mathematical sense, hence, expect none. 

  • Jared could never get lost on a camping trip?


He always knows which way is square. 

  • Jared never gets lost in a new town


For him, all the street corners are square. 

5. What’s the square-headed favorite engineering tool? A set Square. 

The square headed person is an engineer. Or an engineering student. If so, this funny roast will be relatable. A set square is a tool used by engineers in measurements.

It can also be found in the pocket of a square headed person. This is where the humor in this roast is; the fact that the person goes around with a set square. 

  • Why does Jared go around with a set square? Because he’s an engineering student?

Of course, and for good reason. Look at his square head! 

6. What did the square-headed person say when they won the geometry contest? I’m just well-squared in my angles!

Funny Roasts For Someone With a Square Head

This is while others are well rounded in their knowledge, the square headed person is different. 

The humor is found in the wordplay on well-rounded. Prepare to use this roast at the next math or geometry contest.

You can write a speech to be delivered by the person in question, and insert this bit about his well-squared angles. 

  • Congratulations on your win, bro. I guess you’re just well-squared in your angles. 
  • He won the geometry contest because he’s a well-squared guy in his angles. 

7. How does a square headed person keep their thoughts organized? With a squared paper, of course!

The square headed person literally cuts little bits of paper into square shapes. We’re talking fetish level careful cutting here.

Then he applies glue to the back of these little cards and pastes them on his wall: this is the cute way he organizes his thoughts, and his life. 

This is a fun roast on your friend’s special day. Make sure he’s a square headed person, though. 

  • What are the little square papers on Joe’s wall for?

They help him organize his square thoughts. 

  • Do you know why Joe uses square papers for organizing his thoughts?

Bro, look at his square head! 

8. Why did the square headed person become a chef? Because they loved making square meals!

It is only natural that the square headed person would find his way into a kitchen where he cooks, commercially. In this funny roast, the play is on the idea of square meals. 

You can quickly spot the humor when you walk into a restaurant where the square headed person works as a chef.

It would be funny to see him without his chef’s hat, serving his guests, with square plates. 

  • Why did the square headed person become a chef?

Square meals! 

  • Joe is a chef now; guess his favorite line.

Square meals on square plates. 

9. How does a square headed person view the world? From all four corners!

All four corners here refer to the points on the compass: north, south, west and east.

This is a humorous suggestion that the shape of this person’s head allows him to enjoy a full view of the world. 

Use this roast especially for a bald square headed person. 

  • How does a square headed person view the world?

From all four corners of the compass. 

  • Joe sees everything from all corners.

With that square head, he doesn’t have a choice. 

10. What’s a square headed person’s least loved game? Hide and seek. Because they’re always “cornered”!

Here’s another wordplay for your delight. In this funny roast, the square headed person backs out of hide and seek games because, somehow, he’s always caught first. 

And the reason is not far fetched; it’s got something to do with his affinity for corners. So, to catch him, search corners. He’ll be cooped up in one of them—a sitting duck. 

  • Do you know why square headed Joe hates playing hide and seek? 

He always gets found in a corner. 

  • How do you catch square headed Joe in a hide and seek game?

Easy. Just search the corners. 

11. What did the square headed person say when they got a compliment? Thanks for noticing, I’ve got a lot of edge!

Being square headed involves some edges. And this is the humor in this funny roast. Here the square headed person admits the existence of these edges. 

This roast can be told in general terms, even without a square headed person as your audience or target. 

You can tell it as a joke at gatherings to light up the crowd. 

  • What does a square headed person say when you compliment him?

Thanks. I do have a lot of edges. 

  • What did square headed Joe say when you complimented him?

Something about him having fine edges. 

12. Why did the square-headed person become a mathematician? Because they love working with “right angles”!

Funny Roasts For Someone With a Square Head

You know we were going to get here with this roast, didn’t you? What’s a roast about a square headed person without the right angle reference? 

In this roast, we are reminded of the mathematical right angles. Not very different from what you’d find in squares. Your audience should be laughing before you come to the end of this routine. 

  • Square headed Joe now teaches math at the university. 

Oh, really. I knew it. He loved working with the right angles. 

  • Do you know why square headed Joe picked up math as a teacher? 

Everyone knows it has something to do with right angles. 

13. How does a square-headed person open a door? With a “key” square, of course!

Key square, as in an endgame play in chess where only the king and pawns play each other. In this roast the wordplay is on this key square, with emphasis on the square. 

Remember, to make a roast work, play similar words or words with the same meaning. 

In this case, opening the door can be compared to winning the chess game. And the way to do so is through the key square. And of course, the square headed person would prefer this game plan. 

  • How does square headed Joe open a door?

With a key square, of course. 

14. What do you call a square-headed person’s favorite dance move? The Box Step!

The box step is a type of dance that follows a square pattern. Which is why it’s called a box. In this roast, the humor is that a square headed person loves this dance because of the shape it forms on the dance floor. 

Use this roast next prom party for your square headed buddy. If he knows how to dance, even better. Say he’s enjoying the dance because it’s a box step. 

  • What do you call a square-headed person’s favorite dance move?

It’s the box step. 

  • What’s that dance step square headed Joe is doing?

It’s the box step. 

15. What’s the square-headed DJ stage name? MC Squared!

Every math head knows the famous equation: E=mc2. This roast derives it’s meaning from the square in the equation.

The roast imagines that the square headed person is a disc jockey. It is natural that when he chose his nickname it will have a square in it. 

  • Heard Joey is a DJ now. What’s his stage name? 



16. How does a square-headed person play basketball? With a “box out” strategy!

Although the box our strategy is a popular one in basketball, this roast suggests that it’s the favorite for a square headed person. This is so because of the square shape of the box. 

This roast is appropriate for college sports. Use this roast also at a school graduation speech if asked to present an award to someone with a square shaped head. 

  • What’s Joey’s favorite strategy in basketball?

The box out strategy. 

  • How did the college win the basketball competition?

Through square headed Joey’s box out strategy. 

17. Why don’t square-headed people ever lose at chess? Because they’re always one step ahead on the squares!

A chessboard is basically a bunch of squares. And every move involves one or more squares until the end of the game.

In this funny roast, there’s a play on this idea of squares and how the various pieces move on them. When using this funny roast emphasis is laid on squares. 

  • Joey never loses at chess. What’s his secret?

He’s always one step ahead on the squares. 

18. What’s a square-headed person’s favorite type of movie? Anything with “sharp” wit!

In this article, you would have noticed how certain words are used. Words like corner, angle.

And now, sharp. These words paint pictures of what squares basically are. In this roast here, sharp with suggests the sharp edges of squares. 

Combined with the word wit, the humor is subtle. 

  • What kind of movies does square head Joey like?

Any movies with sharp wit. 

19. How does a square-headed person express affection? With “cornered” hugs and “edged” kisses!

This roast is for the standup comedian who’s square headed buddy is in the audience. There’s wordplay here, and word pictures.

Hugs are cornered and kisses are edged, suggesting—who knows? It doesn’t matter. The point here is to connect the words to the square shape of the person’s head. 

  • How does square-headed John express affection?

With “cornered” hugs and “edged” kisses!

20. Why did the square-headed person excel in architecture class? Because they were born to think outside the box!

Any architect would tell you, to excell in the profession, you have to think outside the box. 

For a square headed person, it’s easy. This is because his square headed is already shaped like a box. That’s the humor of this roast. 

  • Why did the square-headed person excel in architecture class?

Because they were born to think outside the box!

Final Thoughts

There’s a roast for everyone. This one has been about the person with a square shaped head. The roasts here are meant to be for light hearted fun and jests.

Not for insults, or meant to embarrass anyone. So keep the language friendly, and respectful when using the funny roasts here. Have fun. 

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