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|Occupation:||Headmaster of Skips' old high school (formerly)|
|Voiced by:||Sam Marin|
|Appears in:||"Skips' Story"|
Headmaster Bennett looks similar to Benson, as he is a gumball machine. He has pinkish-purple gumballs, a grey beard, and small circular glasses. He also wears a navy blue suit with a white shirt and red tie.
- Headmaster Bennett is very similar to Benson. He seems to be even more uptight than him, however. It is entirely possible that Bennett might in fact be Benson's ancestor.