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Pessimist-242 was a perpetually-downcast Mark III Clockwork Cherub, one of the ragtag members of the Blue Feather taskforce.
Description
Personality
Pessimist was uniformly pessimistic and brooding, not seeming to have positive emotions about anything. Some at the Department of Cupid Anatomy went so far as to suggest that he had a negatronic brain instead of a positronic one. He was prone to making acerbic comments about whatever was going on around him. Despite his lack of personal motivation, he did generally go along with what the rest of the Blue Feather were up to, albeit while dragging his feet. (PROSE: Acquaintanceship-982 and the Missing Mail Mystery)
Powers & abilities
Pessimist claimed to have “a positronic brain the side of the Homeworld”.
Like other Cupids, he had the ability to interface with and take control of any technology from the Prime Earth dating back to before the 1960s. (PROSE: Pessimist and the Dromedaries)
Biography
The Whetstone Park epiphany
Although a member of the Blue Feather, Pessimist also sometimes got assigned on solo romanticisation missions. His assigned Fog Ship was the sole result of an ultimately-scrapped project to create artificially-intelligent ships. It had a tendency to misbehave its pilot and wander off on its own errands at inconvenient times, which led the Cupid authorities to assign it to Pessimist because they reasoned that any Cupid given this Ship would complain, but this made no difference for Pessimist insofar as he would complain anyway. One day, by chance, Pessimist was assigned to romanticise people in a Prime Universe public square called Whetstone Park, and got unprecedented good numbers. This was, unbeknownst to Cupid authorities, simply because Whetstone Park was decorated with many copper statues, meaning Pessimist, who stood perfectly still when not loosing arrows, could effectively camouflage himself with no active effort. Because of his “inexplicable” success, Pessimist kept being sent back to this specific location whenever he had to go on a romanticisation mission. (PROSE: Pessimist and the Dromedaries)
Early Blue Feather missions
The Blue Feather were originally housed in a derelict warehouse located on the opposite side of the Mainland Cloud, where Acquaintanceship had to use an upside-down crate as a desk. They weren't given missions of any importance, and indeed, it could be months in-between the missions they did get, disappointing as they were. For example, they once went months without any assignments at all after “the Great Grape Jelly Stain Catastrophe”, their grandiloquent name for the occasion upon which Marmalade-624 spilled grape jelly on his tablecloth and hired the Blue Feather to wash it off. (PROSE: Acquaintanceship-982 and the Missing Mail Mystery)
On April 29th, 2019, (PROSE: The Faction of the Fooling Fish) they were hired by Philatel-426 for an unusually significant operation: locating a bag of mail that had gone missing from the Cupid Post Office. They unsuccessfully interviewed a number of “suspects” — otherwise known as people who happened to be glimpsed at some level of proximity to the Post Office on the day of the crime — but at the last minute, Acquaintanceship realised the truth and actually solved the mystery: Philatel had himself stolen the mailbag, which contained blueprints meant to be transmitted from the Department of Architecture to the Department of Construction so that the latter could begin work on a new giant warehouse. The construction would have involved the destruction of the Post Office's west wing, which was officially vacant, but which Philatel secretly used to store his stamp collection. Rather than turn him in to the Department of Discipline, the Blue Feather blackmailed him into letting them use the selfsame west wing as a new HQ, while convincing the Department of Construction to build their new warehouse on their old site instead.
Just as they were getting settled in, Colonel-028 rushed into their new office with a new mystery to investigate: the theft of a pie from his windowsill. (PROSE: Acquaintanceship-982 and the Missing Mail Mystery) Having badgered badgered the Cupid Parliament into authorising an official investigation, he set the Blue Feather on the task. Following a trail of pie-crumbs, the Blue Feather found a Rift leading to the Faction of the Fooling Fish's headquarters in the Prime Universe, where they briefly confronted the Faction for the first time. After fleeing back through the Rift, they got the Department of Rifts to close it. After the Rifts reopened and had to be closed a second time after a second Fooling Fish incursion, the Blue Feather were assigned to guarding the location of the Rift, in case it opened again. (PROSE: The Faction of the Fooling Fish)
Kidnapped by the Dromedaries
On a romanticisation mission to Whetstone Park, Pessimist was kidnapped by Lila in a burlap sack on behalf of the Drove of the Database-Compiling Dromedaries, a Strangely-Colored Secret Society who devoted themselves to compiling information about other Societies. Brought back to Research Laboratory 6, a listless Pessimist was subjected to many questions and scans from ambitious Head Assistant Researcher Darius. When he realised that Pessimist's absence would be noticed, Darius had a captive Clockmaking Capybara create a cheap duplicate of Pessimist, known thereafter as the Pseudo-Pessimist, and sent it back to the Cupid Homeworld.
Meanwhile, the captive Pessimist was nagged by the Green Gorilla in the cell next to his into orchestrating a mass escape of all the Secret Society mutants in Research Laboratory 6. Primarily, this involved using his ability, as a robotic Clockwork Cherub, to easily hack the electric locks of the cell doors. However, after he freed all the prisoners, they turned to him once again to figure out how to get past the guards and Darius once they climb up from the “dungeon” to the ground floor of the building. At his direction, they lured the guards down, overwhelmed them with diverse, coordinated attacks based on each mutated animal's abilities, and trapped them, one by one, in some of the now-empty cells.
They then used the Camouflaged Chameleon's ability to mimic voices to summon Darius himself to Research Laboratory 6. The animals ambushed Darius and held him in place while Pessimist used his last Cupid Arrow on him, romanticising him. Just as the escapees were about to make it out of the building, the Blue Feather arrived to rescue Pessimist, having recognised Pseudo-Pessimist as an impostor and been brought to his true location by his Fog Ship, whose positronic brain was linked with Pessimist's. Pessimist refused to give them the satisfaction of instantly jumping into the Ship, and, as a result, briefly pretended not to hear them. Darius took this opportunity to steal the Ship, but he had not counted on it having a mind of its own; when he asked to be taken to the Cupid Homeworld, the Ship dropped him in the lap of Lord Thymon, who banished him into the Void Between Worlds while the Ship returned to pick up Pessimist and the Blue Feather. The team, perennially joined by “Pseudo-Pessimist”, then set forth in search of Investigation-464's favourite coat, which the Cupid had misplaced. (PROSE: Pessimist and the Dromedaries)
Watching television
Pessimist was also the owner of a “dodgy” television set on which other members of the Crew of the Copper-Colored Cupids sometimes watched episodes of The Rainbow Adventures. (PROSE: Rifts Crisis Officially Over!) A passing Cupid once saw Pessimist-242 sitting in front of his TV set on a small cloud, looking sullen as usual. When the Cupid pointed out to Pessimist that his TV set was not actually plugged in, Pessimist replied that he knew full well, but didn't think it worth the effort because anything that may actually be on the air would have been just as boring to him as sitting in front of the blank screen as he was already doing. (COMIC: The Pessimist's Guide to the Small Screen)
Further mishaps
The Blue Feather's assignment to watch the Rift endured, although, as it had gone dormant for a while, they only watched it when they had nothing else to do. On one such day, Pessimist, Larrikin-1029 and Dandy-432 were meant to watch the Rift, but Pessimist elected to lie on the ground motionless next to his Fog Ship, instead. As it should happen, it was on this day that the Rift opened again — allowing through not the prank-loving Fish, but a benign old man who was trying to find his way back to his home universe. The two Cupids were surprised to hear that he'd recently met Tracker-764, a legendary Cupid who hadn't been seen in the Homeworld in years. They agreed to help him, only too happy to have a good excuse to leave their post, and the three departed aboard Pessimist's Fog Ship, intent on taking the old man to the Prime Universe and a selection of Prime-adjacent ones to attempt to narrow down his world of origin. Pessimist only resisted very weakly to this borrowing, and remained on the ground. (PROSE: The Mad Cupid of the Euclidean Plane)
Some time later, Pessimist was “wandering about despondently” when a Void Ship appeared in the skies of the Homeworld and began barreling towards him. Reasoning that it would probably find a way to hit him even if he tried to dodge, Pessimist didn't even try, and the ship rammed into him as it crashed. From it, emerged none other than the legendary Tracker himself, who vaguely recognised Pessimist, recalling his name as “Negativeman”. Pessimist was neither very surprised, nor as warmly welcoming as Tracker had hoped of the first Cupid he met in years. (PROSE: Misadventures in the Interdimensional Black Market)
In the Toymaker's Labyrinth
Pessimist was once assigned a mission to Dimension 8696-2537 with Larrikin-1029 as his partner. Both Cupids found this unacceptable, especially as Larrikin had tried to prank Pessimist just a week earlier by putting a tack on his chair, but they didn't manage to sway Taskmaster-523 and departed in Pessimist's Fog Ship for the mission. Irritated by the two Cupids' bickering, however, the Fog Ship didn't take them to Dimension 8696-2537 but to random coordinates which turned out to be those of the gigantic Workshop of Madame Tarsa.
Climbing onto Tarsa's work-table, they were confronted with the Toymaker herself. Fascinated with the Cupids' looks and technology, she decided to try and create a Toy Cupid complete with Love Potion based on samples from the Cupid Arrow Larrikin had tried loosing at her. When Larrikin tried to stop her and ended up damaging the marionette, an irate Tarsa dropped both Cupids, and their Fog Ship (which she shrank down to size and stripped of its dimensional warp drive), into the Labyrinth inside her magic toybox.
After wandering its corridors for some time, the two ended up in Wild West Town, where they were briefly mistaken for new members of the Plush Posse. Even after the misunderstanding was resolved, the Frog Mayor was initially reluctant to let them leave, affecting not to know about worlds beyond the Wild West-themed room, but he changed his tune after realising how annoying the combination of Larrikin and Pessimist could be to have around. Informed by the Mechanical Fortune Teller of the two Cupids' surprising progress, Tarsa sent the Clay Thing to stop them, but it was destroyed by the Fog Ship. They then reached the Doom Room, where Larrikin defeated the giant chess pieces and Pessimist reluctantly foiled the Mechanical Skeleton.
Tarsa entered the Toybox herself and goaded them into a swordfight, making herself the third and final trial of the Doom Room. After the Fog Ship helped the Cupids hold her off and reach the exit, Larrikin destroyed Tarsa's notes and prototypes on Clockwork Cherubs and the Love Potion. Admitting defeat, Tarsa allowed the two to return to the Cupid Homeworld, restoring the Fog Ship to its full size and giving back the dimensional warp drive. Feeling bad about ruining her business idea, Larrikin suggested an alternative one: Thymon Plushies. On the way back, Pessimist informed Larrikin of his skepticism at the idea that such a product could ever be successful. (PROSE: The Toymaker's Labyrinth)
Behind the scenes
Pessimist-242 is a major recurring character in The Crew of the Copper-Colored Cupids.