Jeff / Christian Grey / Jeffrey / Old Jeff / Vice Principal (38 episodes, 2014-2018)
Doug (23 episodes, 2014-2018)
Jim (9 episodes, 2014-2016)
Jessica (4 episodes, 2015)
Cindy (3 episodes, 2014-2016)
Dave (3 episodes, 2014-2016)
January (2 episodes, 2014)
Mr. Morrat (2 episodes, 2015-2016)
Gladys / Mrs. Steinberg (2 episodes, 2015)
Sue (1 episode, 2014)
Mom (1 episode, 2014)
Beth (1 episode, 2014)
Kelly (1 episode, 2014)
Marissa (1 episode, 2014)
Jane (1 episode, 2014)
Jennifer (1 episode, 2014)
Dad (1 episode, 2014)
Club Member (1 episode, 2015)
George (1 episode, 2015)
Dungeon Master (1 episode, 2015)
Todd (1 episode, 2015)
Karen (1 episode, 2015)
Harry Potter (1 episode, 2015)
Kate (1 episode, 2015)
Max (1 episode, 2015)
Self (1 episode, 2015)
Anastasia Steele (1 episode, 2016)
Dina (1 episode, 2016)
Demon (1 episode, 2016)
Dungeon Master (1 episode, 2016)
Demon (Voice) (1 episode, 2016)
Announcer (unknown episodes)