The Most Heart-Breaking Futurama Moment Ever

Futurama may have sprang from the mind of Simpsons creator Matt Groening, but when it debuted in 1999, it quickly developed an identity far removed from its famous sibling. Following the adventures of Philip J. Fry, a bumbling delivery boy who finds himself accidentally transported to the year 3000 and pressed into service as an employee of the failing Planet Express, the series' clockwork sci-fi plots and strongly developed characters made it an instant favorite.

In addition to being one of the most hilarious (and scientifically accurate) animated series of all time, Futurama was imbued from its beginnings with a surprising amount of emotional heft, often having to do with the complicated relationship between Fry and his perpetual love interest, Turanga Leela. When it wasn't tickling our funny bones or bending our brains, the show displayed an earnest willingness to tug at our heartstrings, which it often did masterfully. Throughout its seven seasons (four on Fox, and three on Comedy Central after an extended hiatus), Futurama brought the waterworks early and often — but what is the single most heart-breaking moment in the series' history?

Needless to say, there are a plethora of candidates. Consider the excellent seas 4 episode "The Sting," in which the Planet Express crew are sent on a dangerous mission to collect space honey from, well, space bees. Once in the hive, the mission seems to be going well, but Leela makes a fateful decision to kidnap a baby bee and bring it back to Earth to start a new hive.

Back aboard their ship, though, everything goes sideways. The fuzzy little guy attacks Leela, and Fry throws himself in front of her to protect her, managing to get himself run completely through with the stinger (which only pricks Leela). Fry dies, and Leela is overwhelmed with guilt; in order to sleep, she begins eating spoons full of the space honey, despite Zoidberg's warning that eating too much will cause her to sleep forever.

Leela begins dreaming of Fry, who absolves her of blame and constantly implores her to wake up from her dream. Leela slowly begins to go mad, unable to distinguish between dreams reality; the only constant in her ever-shifting world is the constant, heart-rending guilt of having killed her friend.

Lost in the throes of another bizarre dream, Leela once again encounters Fry, who pleads with her to wake up — which she finally does. It turns out that Fry wasn't killed after all; the stinger did indeed go right through him, but he survived the wound. The small prick, though, gave Leela a full dose of poison, causing her to fall into a deep coma (or, as Bender put it, "the best coma I've ever seen"). Fry had been at her side the entire time, desperately asking her to "wake up" — not from any dream, but from her coma.

Leela's torment over losing Fry, whom she often treats as a nuisance, was truly affecting — but other tear-jerking Futurama episodes served to illustrate that her feelings for her friend run considerably deeper than she lets on. In season 3's "Time Keeps On Slippin'," Professor Farnsworth instructs his crew to collect chronitons, time-altering particles with which he can speed up the growth of his team of genetically engineered mutants. (Why? To win a basketball game against the Harlem Globetrotters, of course.)

The harvesting of the chronitons causes immediate problems, as everyone begins experiencing a series of jarring time skips. As they become more severe, it's revealed that the crew's incursion poses a serious threat to the very existence of the universe, but as Farnsworth works on solving the problem, a particularly robust skip advances everyone to a time when Fry and Leela are improbably married.

Leela is convinced that Fry must have tricked her into marriage somehow, and due to the skip, Fry is unable to remember just what he did to win her over. Meanwhile, the crew manage to temporarily stop the skips by moving stars into formation around the crumbling nebula from which the chronitons were harvested, but they soon resume — and even worsen. The crew deploys a new plan to implode the nebula with a "Doomsday Device," and as Fry moves the Planet Express ship to a safe distance, he gets a look at his handiwork.

Apparently, while everyone had been busy moving stars around, Fry had done a little star-jockeying on the side. He'd moved a group of stars into position to spell "I love you, Leela" across the sky, a grand gesture which had finally thawed her heart. But before Leela can catch a glimpse, the Doomsday Device detonates, pulling all of the stars into a black hole.

Poor Fry. He just can't catch a break.... except when he does, as in the season 3 Futurama episode "The Luck of the Fryrish." In it, Fry becomes fed up with his never-ending run of bad luck, and remembers back to his teen years, when he had a lucky seven-leaf clover that rendered him practically unstoppable in everything from basketball to break dancing. With Leela and Bender, he sets out to search for the clover — which he had stashed in a safe — in the ruins of Old New York City.

They find the safe, but the clover is missing... and it seemingly becomes clear why when the trio discover a statue of Fry's older brother, Yancy, with the clover prominently pinned to his lapel. The inscription on the statue reads "Philip J. Fry — First Person on Mars," leading Fry to understandably conclude that Yancy had assumed his identity, appropriated the clover, and used its luck-bringing powers to earn that designation. (Adding insult to injury, becoming the first person to travel to Mars had long been Fry's dream.)

After a bit of research, the Planet Express crew discover that "Philip" is buried in Orbiting Meadows National Cemetery with the clover, and Fry sets off to pillage the grave (with Bender, who is all too eager to assist). But on the tomb, Fry discovers another life-altering inscription: "Here Lies Philip J. Fry, named for his uncle, to carry on his spirit." Fry realizes that his brother had named his son after him, and in case that wasn't enough to bring on the tears, a flashback to Yancy with the infant Philip J. Fry II seals the deal. 

"Daddy has a present for you today. Do you know what it is?" he asks the child. "It's a lucky clover that can help you be successful whatever you do — even break dancing — and it once belonged to someone very special... Son, I'm naming you Philip J. Fry in honor of my little brother, who I miss every day. I love you, Philip, and I always will."

We mean, come on. Bring the waterworks. The episode may have been remembered as the most poignant in Futurama's entire run, if not for one other — one with a conclusion so utterly devastating that fans could have been forgiven for swearing off the show for a few weeks just to recover. We refer, of course, to the season 4 episode "Jurassic Bark."

Don't let the punny title fool you. The episode opens as Fry and Bender take a trip to the Museum of Natural History to check out a new exhibit which is right in Fry's wheelhouse: 20th century artifacts. Once there, however, Fry realizes that the museum is actually in the same space as the pizza parlor where he used to work — and among the artifacts on display are the fossilized remains of Fry's old dog, Seymour.

Fry manages to convince those in charge to give him his old pooch, and of course, he immediately recruits Professor Farnsworth to attempt to clone Seymour. While the first attempt is foiled by a jealous Bender, the second appears to be going fine — until Farnsworth casually divulges a brutal piece of information. Farnsworth tells Fry that Seymour had been 15 years old when he died, leading Fry to realize that for most of his time on Earth, his old pet was without his master. 

The episode up to this point had included several flashbacks detailing Fry and Seymour's relationship, and as if the implications of Fry's discovery weren't heart-breaking enough, the conclusion drives the point home with one final flashback. It's a montage, showing the passage of years as Seymour sits outside the pizza parlor and waits... and waits... and waits for the return of a master who will never come back. In the final shot, the faithful mutt lays down, closes his eyes... and dies.

Just... wow. Any living thing in front of the television when this particular episode of Futurama aired that was not crying hysterically at its ending must have been a dog themselves, or perhaps a plant. It may be the single saddest moment in all of televised comedy, and as much as we appreciate a little pathos mixed in with our humor, we're perfectly fine with it staying that way.