Weinstein did not land a job on a major comedy series, despite writing numerous
spec scripts for shows such as
Saturday Night Live and
Late Night with David Letterman; he moved back home to Washington, D.C. Their
Seinfeld script and
The Simpsons episode caught the attention of
Diane English, and they were offered a job on a sitcom. Before they accepted this job, they were told that
Jay Kogen and
Wallace Wolodarsky were leaving
The Simpsons, and then joined the writing staff on a permanent basis in 1992, in the
third season of that show. They began as
story editors. They were initially quiet and felt "intimidated", being in the same room as "10 of the greatest minds in comedy", but eventually started pitching jokes with confidence. After season four, most of the original staff left the show. Before
David Mirkin arrived to take over as showrunner for
season five, Oakley, Weinstein, O'Brien and
Dan McGrath were the only writers working on the show and spent a month mapping out most of the season's episodes. "
$pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling)", "
Lisa vs. Malibu Stacy", the show's 100th episode "
Sweet Seymour Skinner's Baadasssss Song" and "
Lady Bouvier's Lover". For
season six they wrote "
Sideshow Bob Roberts", basing much of the episode on the
Watergate scandal, in which they had a great interest, as well as "
Grampa vs. Sexual Inadequacy" and "
Bart vs. Australia". For "Bart vs. Australia", the writing staff wanted to produce an episode in which the Simpsons family traveled to a foreign country; they selected
Australia because they thought that everyone in Australia had a good sense of humor and "would get the jokes", with the episode being intentionally inaccurate. The episode proved somewhat controversial; some Australian fans said the episode was a mockery of their country. Shortly after it had aired, the
Simpsons staff received over a hundred letters from Australians who were insulted by the episode. The pair wrote the two-part episode "
Who Shot Mr. Burns?", which was initially proposed by series creator
Matt Groening. While deciding who the culprit was, Oakley and Weinstein pitched
Barney Gumble because he was a character that could go to jail and it could change the dynamic of the show. Mirkin suggested
Maggie because he felt it was funnier and wanted the culprit to be a family member. Oakley and Weinstein were initially unsure about having Maggie as the culprit, and it was decided that the episode would end with Maggie shifting her eyes and making it look like it was not a complete accident.
As showrunner Oakley and Weinstein were appointed
executive producers and showrunners of the
seventh and
eighth seasons. They were chosen partly because they had been with the show since the third season and understood many of its dynamics. They wanted to produce
Treehouse of Horror episodes, episodes about
Sideshow Bob,
Itchy & Scratchy and several "format-bending" episodes such as "
22 Short Films About Springfield", for which Weinstein wrote the scene featuring
Comic Book Guy and
Milhouse Van Houten. They aimed for "at least two episodes per season that 'pushed the envelope', [and] expanded the definition of what an episode could be". Their preferred choice of guest stars were those with unique and interesting voices, and several of their guest stars were "old grizzled men with distinctive voices" such as
R. Lee Ermey,
Donald Sutherland,
Kirk Douglas and
Lawrence Tierney. Oakley considered season three to be the single greatest comedic season of television ever produced and so attempted to recreate the feel of that season for the two he ran, focusing on stories with real emotions and situations, as well as some
off-the-wall episodes. By the close of the episode, Grimes, a hard working and persevering "real American hero," is relegated to the role of antagonist; the viewer is intended to be pleased that Homer has emerged victorious. Oakley says the episode was "hyper-
meta" and focused on "parodying to some degree the Homer we don't like. That's one of the things that episode is supposed to illustrate — 'Homer gone wrong'. Although, I would argue that in 'Homer's Enemy' he's not even really even all that excessively stupid or immature, actually." When the episode was first broadcast, many fans felt it was too dark, unfunny and that Homer was portrayed as overly bad-mannered. On the DVD commentary, Weinstein considers this episode one of the most controversial of the seasons he ran, as it involves sharp observational humor which many fans "didn't get". Weinstein said that the episode is often misunderstood. Many audiences expected a political satire, while the writers made special effort to keep the parody apolitical. Oakley stresses that "it's not a political attack, it's a personal attack!", and instead of criticizing Bush for his policies, the episode instead pokes fun at his "crotchetiness". Oakley described the episode as a companion piece to "Homer's Enemy", in that a character is juxtaposed alongside Homer and does not get along with him. They considered working on the show to be similar to working in a bubble due to the lack of interference from the Fox network's executives, as is commonplace on other shows. the staff rejected the idea and instead created the episode "
The Itchy & Scratchy & Poochie Show", inserting the one-time character Roy, with no explanation as to who he was, or why he was living with the family, as a reference to the executive's proposal. The episode, which marked the point at which
The Simpsons surpassed
The Flintstones for the number of episodes produced for an
animated series, was named by the
BBC as one of the ten most memorable episodes of the show. They noted "the writers used the opportunity to pay tribute to the art of animation and rail against network interference in their show." The intrusion of the network
censors was limited: the normal procedure is for an episode's script to be sent to the censor and then faxed back with a list of lines and words that should be substituted, causing limited problems as often the offending lines are removed or changed for comedic purposes after animation. The episode "
Homer's Phobia" drew the censor's objections. Its script came back with two pages of notes about almost every single line. The censors stated that they did not like the use of the word "
gay", or the discussion of homosexuality at all, and closed with a paragraph which stated that "the topic and substance of this episode are unacceptable for
broadcast". The censor problems ultimately came to nothing when the episode came back from animation in South Korea, the then-Fox president had just been fired and replaced, with the censors being replaced as well. The new censors sent back merely one line: "acceptable for broadcast".
Leaving the show Oakley and Weinstein stood down as showrunners after season eight because they "didn't want to break [the show]". Oakley said: "We always said we'd never do a joke that we'd done before." "
The Principal and the Pauper" and "
Lisa the Simpson". "The Principal and the Pauper" was negatively received due to the sudden revelation that long-time character
Seymour Skinner was actually an imposter. For example, in his book
Planet Simpson,
Chris Turner describes "The Principal and the Pauper" as the "broadcast that marked [the] abrupt plunge" from
The Simpsons' "Golden Age", which he says began in the middle of the show's
third season. He calls the episode "[one of] the weakest episodes in
Simpsons history". As such, they consider it the most controversial episode from their tenure as executive producers. He and Oakley advise viewers to treat "The Principal and the Pauper" as an "experiment". They surmise that the negative reception was partly due to the fact that it was not immediately apparent to viewers that this was such an episode (as opposed to, for example, "
The Simpsons Spin-Off Showcase"). They describe the ending of the episode as an attempt to reset the continuity and allow fans to consider the episode on its own. "Lisa the Simpson" was their final involvement with the show. The duo wanted to end on a good note—Weinstein stated that the episode "was meant to embody the humor, depth, and emotions of
The Simpsons,"—and they were pleased with the result.
Awards and critical reaction Weinstein won three
Emmys for his work on
The Simpsons, and shared them with the other producers. The previous year, "
Treehouse of Horror VI" was submitted for the award. The staff felt the 3D animation sequence "Homer³" would have given it the edge. The episode eventually lost to
Pinky and the Brain. Oakley later expressed regret about not submitting an episode with a more emotionally driven plot, such as "
Mother Simpson". In 1996, during season seven, the show received a
Peabody Award. Weinstein shared the awards for "
Lisa's Wedding" and "
Trash of the Titans" in 1995 and 1998 respectively. Oakley and Weinstein themselves were nominated, along with the show's composer
Alf Clausen, for the Emmy for Outstanding Individual Achievement in Music and Lyrics for writing "Señor Burns" from "Who Shot Mr. Burns? (Part Two)". Robert Canning of
IGN said the episode "
You Only Move Twice" from season eight "may well be the greatest
Simpsons episode of all time. In my book, it's at least tied," with "
Marge vs. the Monorail".
A. O. Scott described their era as "reach[ing] a pinnacle of zany self-reference with "22 Short Films About Springfield" and "Simpsons Spin-off Showcase"." Weinstein considers the line "Too crazy for Boy's Town, too much of a boy for Crazy Town", from the episode "
Treehouse of Horror VII" to be his favorite joke contribution to the show. The two are popular amongst the show's fans, They pitched the show in 1998 "as an animated series for young adults with a sophisticated,
Simpsons-style sensibility." They aimed to make the show about realistic issues affecting young adults, which were too mature for
The Simpsons. The network was impressed and initially ordered 13 episodes; they ordered five more once the first was completed. The 13 completed episodes were later aired on
Cartoon Network's
adult swim block and the show garnered a worldwide cult following. After lobbying from Oakley and Weinstein, the WB eventually released the series on DVD. Oakley and Weinstein have written and produced several
television pilots. These include a
CBS dramedy entitled
22 Birthdays,
Business Class, a comedy for
NBC about two traveling salesmen,
The Funkhousers, an off-the-wall comedy for
ABC about a close-knit family which was directed by
Frank Oz and
The Ruling Class for
Fox, about a high school class who all got along, regardless of their social group. They have written two feature film screenplays:
The Optimist for
New Line Cinema, in which
Seann William Scott was slated to star as a man born with no unhappiness gene, and
Ruprecht, a
Santa Claus-related comedy for
Disney. Weinstein was due to serve with Oakley as an executive producer on the Fox animated television series
Sit Down, Shut Up in 2009, which was created by
Mitchell Hurwitz. The show, which was based on an
Australian program, featured cartoon characters on live-action backgrounds. However, Oakley ended his involvement with the show due to a contract dispute between the staff and
Sony Pictures. Sony refused to offer a contract which operated under the complete terms of the
Writers Guild of America. Weinstein continued working on the show, before it was canceled after 13 episodes. Weinstein returned to
Futurama, following its revival on
Comedy Central in 2010, and served as a writer and co-executive producer on its
sixth and
seventh seasons. He wrote the episodes "
That Darn Katz!", "
Law and Oracle", "
All the Presidents' Heads", "
A Farewell to Arms", "
Viva Mars Vegas" and
T.: The Terrestrial. Weinstein shared another Emmy for Outstanding Animated Program for the
Futurama episode "
The Late Philip J. Fry" in 2011, being nominated again the following year for "
The Tip of the Zoidberg". and a
Writers Guild of America Award nomination for Outstanding Animation for writing "A Farewell to Arms" in 2013. In 2013, Weinstein co-created, produced and wrote the animated comedy-mystery series
Strange Hill High for British children's channel
CBBC. For the series, Weinstein imported the role of the showrunner and the writer's room, used routinely on American television shows like
The Simpsons, but uncommon on British television. The show uses the animation technique hypervynorama, a mix of puppetry and CGI. Weinstein will also team up with Oakley again to co-write and co-executive produce
22 Birthdays, the failed pilot they originally produced for CBS, as a pilot for
Bravo.
Doug Liman and
Dave Bartis will also be co-executive producers. On September 17, 2021, Weinstein guest starred as a contestant on the YouTube web series, Puppet History. In August 2022, Weinstein appeared in an episode of
Rate My Takeaway where he enjoyed a burger and fries over a chat with the host Danny Malin. Weinstein was a long time fan of the Youtube channel and when Malin was on a tour of the US they arranged the meet up. ==Personal life==