If Mission Hill co-creator Bill Oakley were to guess, there are probably less than 5,000 people who remember his short-lived animated series.

The series ran on The WB from Sept. 24, 1999 to July 16, 2000. Created by Oakley and Josh Weinstein, who were just coming off a very successful run of The Simpsons, Mission Hill seemed like it was poised to be the next great American hit. It followed two brothers, Andy and Kevin French, who didn’t get along but were forced to live with one another.

Set in an undefined metropolis akin to Boston, New York City or San Francisco, Mission Hill was a show about the struggles of compromise. Kevin hates living with his brother and is a social outcast who tries to make it through life by going along with his brother’s oddball schemes. Andy has his heads in the clouds, dreaming of the ideal career while trying to pay rent and deal with his annoying friends. Along with a cast of fellow misfits, including Andy’s girlfriend, Gwen, and their two roommates, Posey and James, Mission Hill was a show about the American dream set in a modern era where that could never become a reality.

Andy, an aspiring cartoonist working a series of odd-end jobs to pay rent in his post-college slump, and Kevin, a brilliant but annoying, know-it-all 17-year-old, were meant to be Felix and Oscar of their time. Mission Hill focused on a group of people that other popular animated shows at the time, including The Simpsons, failed to address: teenagers in their later years and restless twentysomethings.

With all of the ingredients in place — an award-winning team at the helm and a team of animators to help bring the vision to life — what went wrong?

“Warner Bros. goofed,” Oakley told Polygon from his office in Portland, Oregon, laughing. “I'm totally fine with people stealing the episodes on BitTorrent, because Warner Bros. should have gotten their shit together by now."

Oakley and Weinstein both blame Warner Bros. for the show’s lack of success. When Warner Bros. purchased Mission Hill in 1997, The WB was in the process of trying to figure out what kind of network it was going to be. The network was looking for its version of The Simpsons and wanted to take a chance on the two young executives who were having fun on The Simpsons but wanted to explore other ideas they had.

“Warner Bros. should have gotten their shit together by now”

In the period between 1997 and 1999, when The WB debuted Mission Hill, the network had redefined itself, according to Oakley. Shows like Buffy the Vampire Slayer had taken off, and The WB had something to prove: that it could compete with the other big networks. Mission Hill, the network decided, would belong to a late night block of programming that included The Jamie Foxx Show.

At the time, Oakley and Weinstein knew the decision didn’t make any sense. What Jamie Foxx and other creators were doing with their comedy was different from the absurdist humor that Oakley and Weinstein were creating. The two never voiced their concerns to the network, but both now admit to regretting the decision to sign with The WB over other potential networks that showed interest at the time.

“In the time they ordered the show and the time it had appeared on the air, the network had redefined itself,” Oakley said. “They had this leftover programming, and by the time they figured out we shouldn’t be lumped in together, well, let's just say we were in danger of killing that entire network. And we hugely damaged the ratings of those other shows. We had become a liability.”

Knowing that Mission Hill had nothing in common with The Jamie Foxx Show or other series programmed to appear alongside it, Oakley and Weinstein questioned why the network was interested in the program to begin with. Mission Hill wasn’t boundary-pushing, edgy comedy when compared to the shows we have now. It had more in common with a traditional sitcom than anything else, but Weinstein said that by the end of the ’90s, everyone had figured out that The Simpsons wasn’t going away — and everyone wanted a piece of the action.

Between 1998 and 1999, Fox aired the tenth season of The Simpsons. Even with a 12 percent drop in viewership between the ninth and tenth season, each episode saw an average of 13.5 million viewers. It was the third highest rated show on Fox for that year, following Ally McBeal and The X-Files. It was also tied for the 25th most watched show of the season across all major networks and cable broadcasters. The Simpsons may not have been what it was a year or two prior, but there was an audience thirsty for the type of animated storytelling Matt Groening and his team were delivering week after week after week.

Weinstein acknowledged this as the reason The WB showed even a remote interest in Mission Hill. Though he and Oakley never claimed Mission Hill would be the next Simpsons, the executives at The WB were hopeful that they might have stumbled upon their own pot of gold.

“Everyone wanted their own Simpsons,” Weinstein said. “There was a whole rash of other animated shows, and some were great, but most of them sucked. What we believed in and what we sold was the concept that Mission Hill broached an area not covered by The Simpsons.”

Anyone who has seen Mission Hill knows what Weinstein is talking about. There was a uniqueness about the show; everything about Mission Hill was middle class, and the struggles that Andy dealt with were relatable to just about anyone. If Roseanne was the sitcom that redefined how the struggles of the middle class could be used for humor, Mission Hill was one of the first animated series to ask why the medium couldn’t reflect the lives of its creators.

“Everyone wanted their own Simpsons”

Both Weinstein and Oakley have dozens of stories to tell about their friends and the people who inspired Mission Hill. There’s a reason, Oakley said, that the show takes place in a liberal city and is chock full of misfit artists trying to find their place in the world. Even the relationship dynamics between Andy and Kevin were inspired by the creators’ relationships with their siblings and the conversations they had — stories that didn’t quite fit into those seen on The Simpsons.

“This show was a reaction to the fact that The Simpsons doesn't have any characters between the ages of 12 and 25,” Oakley said. “There was nobody in-between them. So we thought, ‘What if we did a show where practically everyone was in that age group?’ We could do a ton of high school stories and a ton of young adult stories, which we couldn't do on The Simpsons. We were trying to avoid the mainstream suburban setting that you were seeing.”

“Besides Otto, there are no teenagers or young adults,” Weinstein added. “That world was never dealt with in The Simpsons. It’s a perfect spot to create an animated show. A lot of it is based on people we knew and friends of ours at that age. We told stories, and those stories made their way to the page.”

“We were naive about the realities of the TV business”

After the show’s eighth season, Weinstein and Oakley left Fox and The Simpsons, armed with a deal to produce Mission Hill at The WB. For inspiration, they drew on experiences of a variety of friends — including those of The Simpsons creator Matt Groening.

While talking about the future he envisioned for his protagonist, Andy, Oakley admitted that he and Weinstein were going to turn him into Groening. They wanted to take what they learned from Groening and the life that the infamous cartoonist led to use a path for Andy to follow — both the good and the bad.

Working closely with Groening allowed Weinstein and Oakley to become friends with the revered figure, but it also led them to understand the struggle that came with fame. Groening, Oakley said, became the basis for where they envisioned Andy ending up at the end of Mission Hill. Giving Andy his own “Matt Groening moment” would have been the perfect end to the series, Oakley said.

“Right after the show ended, Josh [Weinstein] and I talked about picking it up again immediately and what that would look like,” Oakley said. “We had a plan that Andy was going to change every five episodes in his heartbreaking struggle to finally achieve his dream. By season 10, he was going to become Matt Groening, and we were going to bring to light what the reality of the people is for people working on these kinds of series.”

“We knew it would be interesting to track Andy’s career,” Weinstein added. “We thought that was the most interesting angle. And he struggles so much in the beginning, so to have him ultimately successful for who he is would be so satisfying. It would totally allow us to get there by season six or seven or eight or nine, and then we would get to lampoon the TV business, which we also wanted to do.”

Mission Hill was a big dream full of heart and a dedicated team, but it was never given the chance to make a mark. The pain that comes with pouring your heart into something and having it ripped out from under you, Weinstein said, never goes away. Oakley and he still talk about the series and whether or not they could bring it back for a modern audience, with whom it might find more love. Every time they have that conversation, however, Weinstein admits that he couldn’t buy another ticket for the emotional rollercoaster The WB served them.

“Until it got canceled, it was one of the most exciting things ever,” Weinstein said of working on the cartoon. “It was wonderful rollercoaster, one that I never wanted to get off of, until the moment it got canceled — and then it was horrible.

“When you work on The Simpsons, you’re sheltered from the outside world and the industry because you’re protected by Matt Groening,” he said. “When The Simpsons was created, there were no notes from Fox, and Matt continued that deal going forward. The Simpsons is an isolated comedy shelter. When you go out into the real world and try to do your own show, it’s often a big wake up call. Until Mission Hill got canceled, we were naive about the realities of the TV business.”

“I think I really love the tortured history that comes with Mission Hill”

Both Weinstein and Oakley know Mission Hill probably won’t return as a series anytime soon. Oakley said Warner Bros. still owns the rights to the show. Part of that comes with Mission Hill’s cult status: It’s not well known, and both creators know this.

Still, there is hope for those few thousand fans who want the story of Andy and Kevin to continue. Oakley and Weinstein are talking to a few comics publishers about bringing the boys’ stories to the printed page, but there aren’t any solid negotiations at this time. Everything is in its preliminary stage, and both creators are approaching it tepidly. If they learned anything from their time working on Mission Hill, it’s that nothing good ever comes of agreeing to something without considering all the options first.

“You know, looking back on it, there's nothing about Mission Hill creatively that I would change at all, but in terms of the business aspect, I would have done it differently,” Oakley said. “I would have done everything we could have done to get it on a proper network. That's exactly what it is and what it comes down to. I would change everything about it on the business side, in the network we sold it to, how we handled it ... I wouldn’t have done any of that the same way.”

Mission Hill finally went off the air for good, including syndication, in August 2002. While Adult Swim has aired reruns intermittently, and a DVD box set of the complete series is available for purchase, Mission Hill has mostly faded into obscurity. To those who watched the show as it aired or caught wind of it years later, Oakley and Weinstein are grateful.

When asked how he felt about about Mission Hill and everything that happened with it, Oakley went silent. It’s a little uncomfortable and, for a brief second, I consider moving on to the next question. Then a little laugh can be heard on his end of the phone and he sighs.

“I think I really love the tortured history that comes with Mission Hill,” Oakley said. “We spent years obsessing over this, and it didn’t even make it a full 18 episodes. It’s tortured, and I think Andy would have appreciated that. So I have to laugh, because Andy would have loved it.”