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Devan and Quenley Woosterfield  are Simon's half-older brothers and the main antagonists of the The Simpsons episode Double, Double, Boy in Trouble. Them were always trying to kill him to get the family fortune.

Both are voiced by Tress MacNeille 

History

When Bart Simpson switched places with Simon and was almost killed at a ski resort by sliding down an expert track, Devan and Quenley thought he was dead and Quenley may have poisoned Devan with a potato when he mentioned splitting the money fifty-fifty, which Devan seemed to eye the potato suspiciously when she offered it. Milhouse seemed attracted to Devan when he met him.

          The Simpsons Villains

Springfield Republican Party
Birch Barlow | Blue-Haired Lawyer | Lindsey Naegle | Mr. Burns | Waylon Smithers

Terwilliger Family
Cecil Terwilliger | Dame Judith Underdunk | Francesca Terwilliger | Gino Terwilliger | Robert Terwilliger Jr. | Robert Terwilliger Sr.

Springfield Mafia
Fat Tony | Fit Tony

Environmental Protection Agency
Russ Cargill

Recurring Characters
Agnes Skinner | Artie Ziff | Baby Gerald | Constance Harm | Dolph Starbeam | God | Jebidiah Springfield | Herman Hermann | Itchy | Jessica Lovejoy | Jimbo Jones | Kearney Zzyzwicz | Matt Groening | Nelson Muntz | Patty and Selma Bouvier | Senator Mendoza | Snake Jailbird | Space Mutants | Wainwright Montgomery Burns

Treehouse of Horror
Bart (Fly) | Billy the Kid | Count Burns | Gremlin | Groundskeeper Willie | Homer's Clones | Hugo Simpson II | Jonathan Frink Sr. | Kang and Kodos | Killer Krusty Doll | Killer Toupée | King Snorky | Lard Lad | Muttonchop Murderer | Ned Flanders | Seymour Skinner | The Blob | The Collector | The Devil | The Grand Pumpkin | Witch Marge

Guest Star Characters
Adil Hoxha | Adolf Hitler | Andy Hamilton | Bart Simpson's Creatures | Blue-Eyed Man | Bob Arnold | Captain Mordecai Barrows | Cesar & Ugolín | Clownface | Cooder | Comic Book Guy (Brick Like Me) | Devan & Quenley Woosterfield | Dexter Colt | Dwight Diddlehopper | Francine Rhenquist | Frank Grimes, Jr. | French Chef | Hank Scorpio | Howard K. Duff VIII | Ironfist Burns | Jack Crowley | Jim Hope | Julia | Kindergarten Teacher | Larry Kidkill | Lucille Botzcowski | Lyle Lanley | Mav & Portia | Miss Goodthighs | Molloy | Movementarians | Mr. Dirt | Nigel Bakerbutcher | Officer Krackney | Professor Werner Von Brawn | Rex Banner | Robotic Richard Simmons | Shadow Knight | Simon Cowell | Spud | Stanley DeGroot | Stubborn Ape | The Leader | Will Wright