Leopold

Leopold
Sex
Status
Hair	Black (balding)
Occupation	Assistant Superintendent
Relatives	Unknown
First appearance	"Sweet Seymour Skinner's Baadasssss Song"
Voiced by	Dan Castellaneta

Leopold is Superintendent Chalmers' assistant. He is a large, surly, snarling man. When Principal Skinner had to be replaced, Leopold stomped in, issued several threats, horrified children by making them think he was the replacement, and then suddenly politely introduced the actual substitute, Ned Flanders. The children then collectively sighed with relief. The gag was repeated when Marge Simpson became a substitute teacher when the teachers go on strike.

Behind the Laughter

• He is one of the few characters on The Simpsons to have eyebrows.
• A similar gag was used in "Mayored to the Mob" when Leavelle starts berating his students, and makes it seem as though his students are going to fail his academy, he then suddenly tells them that they've graduated from his class.
• He appears in The Simpsons: Tapped Out as a limited time premium character for the Rommelwood Academy 2017 event and players can get him upon the completion of the Enriched Learning Center for Gifted Children which comes with him. He later appeared in a 2018 event.

Gallery

The full image gallery for Leopold may be viewed at Leopold/Gallery.

Appearances

• Episode – "Sweet Seymour Skinner's Baadasssss Song"
• Episode – "Homer the Great"
• Episode – "The PTA Disbands"
• Episode – "Who Shot Mr. Burns? (Part One)" (Seen at the Oil Appreciation Day)
• Episode – "22 Short Films About Springfield"
• Episode – "Simple Simpson"
• – The Simpsons Movie
• Comic book – Bart Simpson Comics 5 "Bart Simpson's Day Off"
• Comic book – Bart Simpson Comics 24 "Bart's Got Spirit!"
• Video game – The Simpsons: Tapped Out

The Simpsons: Season Five
"Homer's Barbershop Quartet":	"Cape Feare":	"Homer Goes to College":	"Rosebud":	"Treehouse of Horror IV":
Absent	Absent	Absent	Absent	Absent
"Marge on the Lam":	"Bart's Inner Child":	"Boy-Scoutz 'n the Hood":	"The Last Temptation of Homer":	"$pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling)":
Absent	Absent	Absent	Absent	Absent
"Homer the Vigilante":	"Bart Gets Famous":	"Homer and Apu":	"Lisa vs. Malibu Stacy":	"Deep Space Homer":
Absent	Absent	Absent	Absent	Absent
"Homer Loves Flanders":	"Bart Gets an Elephant":	"Burns' Heir":	"Sweet Seymour Skinner's Baadasssss Song":	"The Boy Who Knew Too Much":
Absent	Absent	Absent	Minor	Absent
"Lady Bouvier's Lover":	"Secrets of a Successful Marriage":
Absent	Absent

The Simpsons: Season Six
"Bart of Darkness":	"Lisa's Rival":	"Another Simpsons Clip Show":	"Itchy & Scratchy Land":	"Sideshow Bob Roberts":
Absent	Absent	Absent	Absent	Absent
"Treehouse of Horror V":	"Bart's Girlfriend":	"Lisa on Ice":	"Homer Badman":	"Grampa vs. Sexual Inadequacy":
Absent	Absent	Absent	Absent	Absent
"Fear of Flying":	"Homer the Great":	"And Maggie Makes Three":	"Bart's Comet":	"Homie the Clown":
Absent	Cameo	Absent	Absent	Absent
"Bart vs. Australia":	"Homer vs. Patty and Selma":	"A Star is Burns":	"Lisa's Wedding":	"Two Dozen and One Greyhounds":
Absent	Absent	Absent	Absent	Absent
"The PTA Disbands":	"'Round Springfield":	"The Springfield Connection":	"Lemon of Troy":	"Who Shot Mr. Burns? (Part One)":
Minor	Absent	Absent	Absent	Cameo