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Headmaster Bennett is one of the characters who appears in the Regular Show episode Skips' Story. He was the headmaster of Skips' old high school.


Headmaster Bennett looks similar to Benson, being 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, although he seems to be even more uptight. 
  • It is entirely possible that Bennett is a distant ancestor of Benson's. 
  • Alongside with Benson, Sam Marin also uses his natural speaking voice for voicing Headmaster Bennet.