Leopold

Leopold 200px

Character Information Gender: Male ♂ Status: Unknown Age: 58 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 temporarily replaced, Leopold stomped in, issued several threats, and terrified 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 Scenes

He is one of the few characters on The Simpsons to have eyebrows.

Appearances

• Episode – "Sweet Seymour Skinner's Baadasssss Song"
• Episode – "Homer the Great"
• Episode – "The PTA Disbands"
• Episode – "Who Shot Mr. Burns? (Part One)"
• Episode – "22 Short Films About Springfield"

The Simpsons characters

The Simpsons and relatives Jacqueline Bouvier • Patty Bouvier • Selma Bouvier • Abraham Simpson • Bart Simpson (Bartman • El Barto) • Homer Simpson • Lisa Simpson • Maggie Simpson • Marge Simpson • Mona Simpson Jub-Jub • Plopper • Santa's Little Helper • Snowball II Around Springfield Kumiko Albertson • Ms. Albright • Jasper Beardsley • Benjamin • Blue-haired lawyer • Brittany Brockman • Señora Bumblebee Man • Shauna Chalmers • Comic Book Guy • Crazy Cat Lady • Larry Dalrymple • Doug • Eddie • Maude Flanders • Ned Flanders • Julio Franco • Jonathan Frink • Gary • Alice Glick • Barney Gumble • Gil Gunderson • Constance Harm • Bernice Hibbert • Julius Hibbert • Julius Hibbert's daughter • Julius Hibbert's oldest son • Lionel Hutz • Jacques • "Just stamp the ticket" man • Princess Kashmir • Hyman Krustofsky • Akira Kurosawa • Cookie Kwan • Grady Little • Lou • Helen Lovejoy • Jessica Lovejoy • Timothy Lovejoy, Jr. • Barry Mackleberry • Jerri Mackleberry • Jack Marley • Horatio McCallister • Milo • Hans Moleman • Marvin Monroe • Eddie Muntz • Mrs. Muntz • Bleeding Gums Murphy • Lindsey Naegle • Nahasapeemapetilon octuplets (Anoop • Gheet • Nabendu • Poonam • Pria • Sandeep • Sashi • Uma) • Apu Nahasapeemapetilon • Manjula Nahasapeemapetilon • Sanjay Nahasapeemapetilon • Old Jewish man • Ruth Powers • Gareth Prince • Gloria Prince • Joe Quimby (Mayor Quimby's body guards) • Martha Quimby • Raphael • Luigi Risotto • Nick Riviera • Sam • Gerald Samson • Agnes Skinner • Roy Snyder • Spuckler children (Dubya • Whitney) • Brandine Spuckler • Cletus Spuckler • Squeaky-voiced teen • Strawberry • Disco Stu • Moe Szyslak • Kirk Van Houten • Luann Van Houten • Clancy Wiggum • Sarah Wiggum • Yes Guy • Artie Ziff Celebrities Bill and Marty • Booberella • Kent Brockman • Bumblebee Man • Scott Christian • Duffman • Matt Groening • Krusty the Clown • Lurleen Lumpkin • Troy McClure • Sideshow Mel • Roger Meyers, Jr. • Arnie Pye • Pyro • Dave Shutton • Jebediah Springfield • Miss Springfield • Drederick Tatum • Mr. Teeny • Rainier Wolfcastle (McBain) Springfield Elementary School faculty and students Chuck Berger • Black weasel • Wendell Borton • Gary Chalmers • Lewis Clark • Database • Lunchlady Dora • E-mail • Rod Flanders • Todd Flanders • Ham • JJ Hibbert • Elizabeth Hoover • Sophie Jensen • Jimbo Jones • Edna Krabappel • Coach Krupt • Dewey Largo • Sherri Mackleberry • Terri Mackleberry • Otto Mann • Audrey McConnell • Nelson Muntz • Nell Nicholson • Brunella Pommelhorst • Janey Powell • Martin Prince • J. Loren Pryor • Report Card • Richard • Dolph Shapiro • Becky Shorter • Nina Skalka • Seymour Skinner • Cosine Tangent • Allison Taylor • Milhouse Van Houten • Wanda • Ralph Wiggum • Groundskeeper Willie • Hubert Wong • Yellow weasel • Jaffee Ziswhisky • Üter Zörker • Kearney Zzyzwicz Blond-haired boy with glasses • Brown-haired boy • Buck-toothed boy • Buck-toothed girl • Girl with glasses • Lewis look-alike • Long haired girl Springfield Nuclear Power Plant Blinky • Charles Montgomery Burns (The Hounds) • Carl Carlson • Charlie • Lenny Leonard • Waylon Smithers, Jr. • Smitty Villains Sideshow Bob • Frankie the Squealer • Herman Hermann • Snake Jailbird • Kang Johnson • Kodos Johnson • Legs • Louie • The Rich Texan • Hank Scorpio • Johnny Tightlips • Fat Tony Other characters Capital City Goofball • Jesus Christ • Santa Claus • Devil • Fallout Boy • Itchy • God • Leprechaun • Richard Nixon • Poochie • Radioactive Man • Scratchy Families The Simpsons • The Bouviers • The Flanderses • The Hibberts • The Krustofskys • The Lovejoys • The Spucklers • The Van Houtens • The Wiggums • The Muntzes Miscellaneous Doppelgängers • Fictional characters • LGBT characters • Animals • Deceased characters • Crossover characters • One-time characters • Recurring characters • Non-canon characters