March 28, 1999 (1999-03-28) – August 10, 2003 (2003-08-10)
March 23, 2008 (2008-03-23) – present
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Futurama is an animated science-fiction comedy show, which was also created by Matt Groening. Numerous references have been made to the show throughout the run in The Simpsons as well as Futurama making references to The Simpsons. Many people have compared the Futurama main characters with the main Simpsons characters such as Bender is Futurama's Homer. A running joke is that on The Simpsons, Futurama is a fictional cartoon show. On Futurama, however, it is The Simpsons that is a fictional cartoon show.
"Catch 'Em if You Can": There is a Futurama poster hanging on the video game store's wall.
"Future-Drama": Bender appears when Homer and Bart pass through the tunnel with John DiMaggio reprising his role. The episode's title is a reference to Futurama itself.
"Treehouse of Horror XIX": Bart, when looking for a present for Lisa, picks up a bottle with a crude picture of Fry hung on the side of it.
"Bart Simpsons comics": In an issue, Bart has taken over Comic Book Guy's stall at the comic book convention. Suddenly the doors open and thousands of kids rush towards Bart's booth, asking him to trade their comics with him (since the stall was a kinda Comic trade center). One of them being a kid who wants to trade his Futurama comic which his cat "peed on".
In return, there have been a few references to The Simpsons on Futurama.
"Space Pilot 3000": when Fry passes through an underwater tube, Blinky briefly appears (which in different colour) in the water below him. Also, in an early storyboard of this episode, Fry is watching The Simpsons. And he says Woo Hoo.
"My Three Suns": one of Bender's badges at the bottom of his sash has a profile of Homer.
"A Big Piece of Garbage": on the trash asteroid, a pile of Bart Simpson dolls can be seen. Bender picks up one and hears Bart say his catchprase, "Eat my shorts". Bender complies and eat them and mimics Homer in saying "Mmm... shorts". Nancy Cartwright voiced the Bart Simpson doll.
"Hell Is Other Robots": when Fry and Leela open the door to the Robot Hell, a heart with an arrow through reads "H.S. 4 M.B.". This means "Homer Simpson for Marge Bouvier" (later Simpson).
"Mars University": Homer and Bart toys appear as prizes at the "Coney Island College".Homer and Bart
"Leela's Homeworld": Bart's face appears in as part of the hot air balloon the main characters use to escape the sewers.
"Jurassic Bark": the hole of the miniature windmill is closed until further notice due to someone being inconsiderate and creating an unsanitary condition. This this is a reference to "Natural Born Kissers" in which Homer and Marge have sex at a minigolf windmill.
"The Sting": The thing with Leela staring into the coffin was similar to when Homer was on a vibrating chair going so fast that during a scene, whenever he blinked, his eyes and skin changed to different colours.
In reference to the longevity of the show, it was stated that in the year 3000 The Simpsons are still on the air and keep producing original episodes even over one thousand seasons.
"Hostile Makeover": The wig Amy puts on Leela about halfway through the comic is the same style as Marge's from the simpsons.
"Lrrreconcilable Ndndifferences": Matt Groening's head appears at the comic con giving a sneak preview of a show he created called Futurella (a self-parody of Futurama, right down to the opening credits and the fact that it was cancelled before its time). Bender asks Matt Groening when he is going to make a second Simpsons movie, and Groening responds by shooting at Bender.