Top 10 Puns, Jokes and Wordplays in Undertale

The Top Ten

Sans & Papyrus (Fonts)
Alphys (shy pal)
WD (Wing Dings) Gaster
(Terezi) Pyrope
Hotland (Holland)
"What does a skeleton decorate his roof with? SHIN-gles!"
"I've gotten a ton of work done today...a SKELE-ton!"
"Put a little more BACKBONE into it!"
"Why did the skeleton want a friend? Because he was feeling BONELY!"

The Contenders

"You never gained any LOVE, but you gained love."
Delta Rune (Undertale)
Asriel Dreemurr (Serial Murderer)
Asgore Dreemurr (Sage Or Murderer)
Toriel (Tutorial)
"The souls of monsters are vastly weaker than those of humans! The soles of our SHOES, on the other hand...are about the same!"
Snowdrake is pleased with its "cool" joke.
"You can feel your SANS crawling on your back."
Undyne (Undying)
Undyne (Undine)
Tsunderplane (Tsundere Airplane)
"You really like hot animals, don't you, kid?"
(Little Miss) Muffet
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