diff --git a/tux/cogs/fun/cowsay.py b/tux/cogs/fun/cowsay.py
new file mode 100644
index 00000000..5f63eb6b
--- /dev/null
+++ b/tux/cogs/fun/cowsay.py
@@ -0,0 +1,123 @@
+from textwrap import wrap
+
+from discord.ext import commands
+
+from tux.bot import Tux
+from tux.utils.flags import generate_usage
+
+
+class Cowsay(commands.Cog):
+    def __init__(self, bot: Tux) -> None:
+        self.bot = bot
+        self.cowsay.usage = generate_usage(self.cowsay)
+
+    # Helper function that word-wraps text and surrounds it with an ascii art box
+    async def draw_textbox(self, message: str, curviness: bool) -> str:
+        message_lines = wrap(message, 40)
+        max_line_length = max(len(line) for line in message_lines)
+        corners = ["╭", "╮", "╰", "╯"] if curviness else ["/", "\\", "\\", "/"]
+        border = f"{corners[0]}{'-' * (max_line_length + 2)}{corners[1]}\n"
+
+        message_box_lines = [
+            border,
+            *[f"| {line}{' ' * (max_line_length - len(line))} |\n" for line in message_lines],
+            f"{corners[2]}{'-' * (max_line_length + 2)}{corners[3]}",
+        ]
+
+        return "".join(message_box_lines)
+
+    @commands.hybrid_group(
+        name="cowsay",
+        aliases=["cow"],
+    )
+    @commands.guild_only()
+    async def cowsay(
+        self,
+        ctx: commands.Context[Tux],
+        message: str,
+        creature: str = "cow",
+        eyes: str = "o",
+        curviness: bool = True,
+    ) -> None:
+        """
+        cowsay command
+
+        Parameters
+        ----------
+        ctx : commands.Context[Tux]
+            The context object for the command.
+        message : str
+            The message to encode
+        creature : str
+            Which creature to use for the drawing
+        curviness: bool
+            whether to use slashes or curves for the box corners
+        eyes: str
+            What char to use for the eyes
+        """
+
+        # Creature dict. "?" will be replaced with the user-specified eye character.
+        creatures = {
+            "cow": r"""
+    \   ^__^
+     \  (??)\_______
+        (__)\       )\/\
+            ||----w |
+            ||     ||""",
+            "tux": r"""
+    \
+     \   .--.
+        |?_? |
+        |:_/ |
+       //   \ \
+      (|     | )
+     /'\_   _/`\
+     \___)=(___/""",
+            "puffy": r"""
+    \
+     \         |    .
+           .   |L  /|
+       _ . |\ _| \--+._/| .
+      / ||\| Y J  )   / |/| ./
+     J  |)'( |        ` F`.'/
+   -<|  F         __     .-<
+     | /       .-'. `.  /-. L___
+     J \      <    \  | | ?\|.-'
+   _J \  .-    \/ ? | | \  |F
+  '-F  -<_.     \   .-'  `-' L__
+ __J  _   _.     >-'  )._.   |-'
+ `-|.'   /_.           \_|   F
+   /.-   .                _.<
+  /'    /.'             .'  `\
+   /L  /'   |/      _.-'-\
+  /'J       ___.---'\|
+    |\  .--' V  | `. `
+    |/`. `-.     `._)
+       / .-.\
+ VK    \ (  `\
+        `.\ """,
+        }
+
+        if message == "":
+            await ctx.send("Error! Message is empty!")
+            return
+
+        if creature not in creatures:
+            keys = list(creatures.keys())
+            valid_creatures = ", ".join(keys[:-1]) + " and " + keys[-1] if len(keys) > 1 else keys[0]
+            await ctx.send(
+                f'Error: "{creature}" is not a valid creature! Valid creatures are: {valid_creatures}',
+                ephemeral=True,
+            )
+            return
+
+        if len(message) > 250:
+            await ctx.send(f"Error! Message too long! ({len(message)} > 250)")
+            return
+
+        textbox = await self.draw_textbox(message, curviness)
+        await ctx.send(f"```{textbox}{creatures[creature].replace('?', eyes[0])}```")
+
+
+async def setup(bot: Tux) -> None:
+    await bot.add_cog(Cowsay(bot))