Leopold

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, and horrified the children, 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

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

view • talk • edit The Simpsons Characters
The Simpsons and relatives
Homer Simpson • Marge Simpson • Bart Simpson • Lisa Simpson • Maggie Simpson Santa's Little Helper • Snowball II • Abraham Simpson • Patty Bouvier • Selma Bouvier • Mona Simpson • Jacqueline Bouvier • Ling Bouvier • Herb Powell
Around Springfield
Jasper Beardly • Comic Book Guy • Barney Gumble • Maude Flanders • Ned Flanders • Professor Frink • Gil Gunderson • Julius Hibbert • Lionel Hutz • Helen Lovejoy • Reverend Timothy Lovejoy • Captain Horatio McCallister • Akira • Hans Moleman • Marvin Monroe • Bleeding Gums Murphy • Apu Nahasapeemapetilon • Mayor Joe Quimby • Dr. Nick Riviera • Agnes Skinner • Cletus Spuckler • Disco Stu • Squeaky-Voiced Teen • Moe Szyslak • Sam and Larry • Kirk Van Houten • Luann Van Houten • Clancy Wiggum • Eddie • Lou • Crazy Cat Lady • Lindsey Naegle • Cookie Kwan • Wiseguy • Brandine Spuckler • The Yes Guy • Sanjay Nahasapeemapetilon • Blue-haired Lawyer • Judge Roy Snyder • Rich Texan • Luigi Risotto • Old Jewish Man • Mrs. Glick
Media Personalities
Itchy & Scratchy • Kent Brockman • Krusty the Clown • Troy McClure • Sideshow Mel • Rainier Wolfcastle | Arnie Pye • Radioactive Man • Duffman • Bumblebee Man • Bill and Marty • Drederick Tatum • Mr. Teeny • Scott Christian • Booberella • Gabbo • Lurleen Lumpkin • Celebrities
Springfield Elementary School faculty and students
Superintendant Chalmers • Seymour Skinner • Edna Krabappel • Elizabeth Hoover • Groundskeeper Willie • Otto Mann • Lunchlady Doris • Dewey Largo • Dr. J. Loren Pyror • Milhouse Van Houten • Ralph Wiggum • Nelson Muntz • Martin Prince • Rod Flanders • Todd Flanders • Sherri and Terri • Wendell Borton • Database • Jimbo Jones • Kearney Zzyzwicz • Dolph Starbeam • Üter Zörker • Janey Powell • Lewis • Richard • Bashir bin Laden
Springfield Nuclear Power Plant
Charles Montgomery Burns • Waylon Smithers • Carl Carlson • Lenny Leonard • Charlie • Blinky
Villains
Snake Jailbird • Kang & Kodos • Herman • Sideshow Bob • Fat Tony • Frankie the Squealer • Johnny Tightlips • Legs and Louie
Families
The Simpsons • The Bouviers • The Flanders • The Van Houtens • The Wiggums
Miscellaneous
Fictional characters • One-Time Characters • LGBT characters • Parodied celebrities • Animals