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Many times throughout the series, caricatures of the staff appear in the show.
- "Bart Gets Famous": Conan guest stars as himself, and Bart appears on his talk show.
- "Radioactive Man": When Homer is flipping through channels, he passes Conan's show.
- $pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling): He appears as a hobo when Grampa and Jasper are walking down the street. This hobo characiture also appears in Homer Loves Flanders in the homeless shelter and in You Only Move Twice during the Syfer's Creek video.
- In the disc holder artwork for The Complete Tenth Season, James appears in a crashed studio lot cart.
- He guest stars as himself in "A Star Is Born-Again".
- "I Am Furious (Yellow)": He is voice actor who plays Angry Dad.
- "Homer Simpson, This Is Your Wife": The studio cart passes him in the Fox Studio.
- "He Loves to Fly and He D'ohs": Is in a play.
- "The Itchy & Scratchy & Poochie Show": He is part of the staff for Itchy and Scartchy.
- "The Front": He can be seen in the audience during the award show.
- "The Boy Who Knew Too Much": He appears as the courtroom artist.
- "My Big Fat Geek Wedding": He guest stars as himself at the sci-fi convention.
- "22 Short Films About Springfield": He is one of the people laughing at Nelson when his pants are pulled down.
- "Treehouse of Horror X": He is one of the celebrities captured by The Collector.
- In the couch gag for "Guess Who's Coming to Criticize Dinner?" that has Matt Groening's autograph on the floor and Marge cleans only to have Matt rewrite it.
- "Worst Episode Ever": His picture is on the wall of people who are banned from Comic Book Guy's store.
- In the couch gag for "Blame It on Lisa" that has the family as puppets, Matt is revealed to be the operator of them.
- The couch gag for "Don't Fear the Roofer" Matt yells woo hoo after Homer's hand finishes a puzzle.
- In the disc holder artwork for The Complete Tenth Season, Matt appears in a crashed studio lot cart.
- He appears as a boss in The Simpsons Game.
- "The Front": He is among the Itchy & Scratchy writers. He also appears in the audience of the awards where he says he'll quit his current job to write a sitcom about a sassy robot.
- "The Simpsons Spin-Off Showcase": She appears on a poster for Rohda in the Museum of TV and Television.
- "The Simpsons Spin-Off Showcase": The character Betty is a cariciture of herself. Betty is also played by her.
- "The Itchy & Scratchy & Poochie Show": He is part of Itchy and Scratchy's writing staff and gets fired.
- "Realty Bites": He appears behind Kirk Van Houten at the unemployment office.
- "Special Edna": He is one of the men Bart thinks of that would be good for his teacher to date.
- "Jazzy and the Pussycats": He is passed by Bart on the street.
- "22 Short Films About Springfield": They are part of the crowd that laughs at Nelson.
- "The Homer They Fall": A poster in Moe's office says "Szyslak vs. Oakley" and has a picture of Bill Oakley's head.
- "The Itchy & Scratchy & Poochie Show": They appear as part of the writing staff for Itchy and Scratchy.
- "The Front": He is among the Itchy & Scratchy writers.
- "Marge Simpson in: "Screaming Yellow Honkers"": He appears with his family running away from a rhino at the zoo.
- "Simpsons Bible Stories": Mike's children can be seen in a crowd at one point.
- "How I Spent My Strummer Vacation": He is one of the men in line for the bathroom at the concert.
- In the disc holder artwork for The Complete Tenth Season, Mike can be seen going in Homer's celebrity museum from "When You Dish Upon a Star".
- "Marge vs. the Monorail": He is one of the people that falls off the "Escalator to Nowhere".
- "The Itchy & Scratchy & Poochie Show": He is the sketch artist who draws out the first sketch of Poochie.
- "The Front": He appears among the Itchy & Scratchy writers.
- "Home Sweet Homediddly-Dum-Doodily": A statue of him appears outside the courthouse.
- "Bart the Fink": He appears at Krusty's fake funeral.
- "The Day the Violence Died": He is one of Lionel Hutz's surprise witnesses.
- "Bart After Dark": He is seen sitting in front when Homer first looks in the main stage area.
- "Hurricane Neddy": He is one of the people the family passes while walking through the mental hospital.