Several years prior to the Great War, the brothers Charles and Jules were students of Nate Morgan, the Overlander who created the Power Rings. During this time, Jules fell in love with another hedgehog called Bernie as the two would often spar in class debates.
Great War Years
As they got older and the Great War began, the brothers became soldiers for the Kingdom of Acorn. When the two stumbled across the exhausted and beaten Julian Kintobor during a scouting mission in the Badlands, Charles opted against rescuing him as he felt something was suspicious about the Overlander. However, Jules insisted, saying they were better than their enemies.
During the Overlander's siege of Mobotropolis, the brothers were part of a small group of troops that managed to take refuge in the city's underground catacombs, only to be led behind enemy lines by Bernadette and Cocoa. Due to the element of surprise, the task force was able to chase off the Overlanders, defeating or capturing all but the commanding officer of the unit, Colin Kintobor.
For his services during the Great War, Sir Charles was knighted personally by King Maximillian Acorn.
Some time later, Jules and Bernadette got married and their son was born on day 162 of year 3220 (i.e. June 23, 3220). While his parents originally named him after his grandfathers, Sonic quickly picked up his nickname due to his incredible speed which he would use to run everywhere.
Jules was part of a small task force employed to seek out and recover the infamous historian Kirby. While on the mission the group encountered a lone Overlander soldier. In his haste to capture the enemy, Jules was caught off guard and received a mortal wound. The enemy troop was subsequently defeated by Bernadette, and Jules was brought back to Mobotropolis to undergo treatment.
The First Robian
The wound he obtained however, proved fatal unless drastic alternative measures were taken. With no other alternative to save his brother's life, Charles decided there was only one hope to save Jules: the Roboticizer. Unbeknownst to Charles, Warlord Julian had already tampered with the machine, and upon Jules' roboticization, he became little more than a mindless drone. Robbed of his free will, Jules was rendered a mindless tool that Robotnik had the audacity to manipulate into roboticizing Bernadette.
When Bernie discovered that Julian was using Jules for lab work, she confronted him. However, Julian simply used his control over Jules to capture and throw Bernie into the roboticizer. Soon she too was roboticized and was robbed of her free will. When Charles came looking for her, Julian lied and said that Bernie was fooling around with the roboticizer and ended up her current state, adding on to Charles' grief.
Following Julian's (now renamed Dr. Ivo Robotnik) takeover, Jules and Bernadette worked as two of the many Robians in Robotropolis. Charles kept her and Jules' existence unknown to Sonic until after Robotnik's death, as he realized Robotnik would have used them to make Sonic's emotions consume his judgement and likely result in his capture. Charles and Sonic's pet dog Muttski would be among the first to be roboticized following Robotnik's takeover.
Lives as Robians
Years later, Charles regained his free will after Robotnik opened up the Void. Following this, he sought out his brother and helped to restore his free will with a Power Ring, along with that of Bernadette and a few other Robians. Those who had their free will restored joined an underground network in Robotropolis to help the Freedom Fighters against Robotnik.
Unwilling to let his uncle remain a robot, Sonic worked together with Rotor Walrus to try and devise a De-Roboticization method to turn Chuck and Muttski back into their normal selves. Their efforts were unsuccessful, and they were forced to abandon the attempt when word reached them of Robotnik's new army of Combots, battle machines superior to SWATbots that possessed the power to destroy Knothole. Unfortunately, Chuck's return to Robotropolis to neutralize them played into Robotnik's hands, and both Charles and Muttski had their Robian programming re-initialized. With Chuck's knowledge, Robotnik's army marched on Knothole, and the Freedom Fighters found themselves at the mad doctor's mercy—or so Robotnik thought. In truth, Rotor had installed Neuro Overrider units in Chuck and Muttski, permitting them to retain their free will no matter what Robotnik tried. Reprogramming the Combots, Chuck easily neutralized the threat, all the while cementing Robotnik's belief that he remained a loyal, mindless slave.
Chuck continued to provide intelligence up until the fall of Dr. Robotnik, including the danger posed to their primitive ally Mobie by Robotnik's machinations in the Great Jungle with his Eco-Destroyer, a weapon intended to destroy the jungle which Robotnik feared and hated. He was then invited along on one of Sally's military retreats, a chance for the Freedom Fighters to reflect on their past efforts, following his display of guilt for allowing Robotnik to seize the Roboticizer. With the arrival of first the Wolf Pack Freedom Fighter group and then Geoffrey St. John, Chuck learned that he was the target of both prejudice and suspicion, as Geoffrey had been following him since the Sleuth Dog incident and now believed him to be a double-agent working for Robotnik. Painful as that must have been, Chuck was then confronted with worse as Sonic was arrested by St. John's Rebel Underground on suspicion of having killed Sally. Charles refused to believe the charges, and even provided Sonic with information regarding a traitor amidst the Freedom Fighters, who turned out to be Drago Wolf, an abusive and power hungry Wolf Pack member who framed Sonic and nearly brought about Sally's death. He was then amongst those taken prisoner by Dr. Robotnik when an Auto Automaton of King Max betrayed Knothole to the dictator. Thanks to the brave actions of Sonic and other allies, however, Chuck was freed just in time to see Robotnik overthrown.
When Doctor Eggman made a broadcast over the Kingdom's new television network, Chuck was one of the many watching, his old guilt renewed as Robotnik's biographical program brought up his part in creating the Roboticizer. Perhaps seeking solace, he traveled to the Mobotropolis library and found Amy Rose and Miles "Tails" Prower speaking with the librarian, Jeremiah, about the events preceding Robotnik's rise to power. Afterwards, he participated in his brother Jules' and Bernie's wedding vow renewal, providing them with Power Ring commemoration bands, which brought him to contemplate how he had for so long received credit for the creation of the rings instead of Nate. Sonic and Nate then left Knothole, where the ceremony had taken place, only to return later to find it empty, courtesy of Eggman's satellites and their teleportation system. When Sonic finally found Uncle Chuck again, Dr. Eggman had restored his Robian programming despite Rotor's Neuro-Overrider, and with all the Robians—except for Sonic's parents, who escaped using Power Rings—Chuck was sent back to the recaptured Robotropolis as Dr. Eggman's slave.
Eggman remained under the impression that Uncle Chuck was his devoted servant despite a "temporary" release through the power of the Sword of Acorns. However, Chuck was once again playing the part of mindless drone, revealing himself after seeing Uma Arachnis steal the Sword of Acorns after Eggman cast it aside in frustration. Even though he longed to rejoin the Freedom Fighters, he continued acting as Robotnik's agent, joining a horde of Robians that forced Sonic to flee Robotropolis rather than risk hurting them. Realizing the danger of the Sword in the hands of Uma's ally Kodos, he reprogrammed one of Eggman's Shadowbots to deliver a message regarding the Sword's status to Sonic in Knothole. However, Geoffrey St. John destroyed the robot and seized it before it could complete the message.
Soon afterwards, Chuck was among the many Robians who disappeared mysteriously, only to return one by one restored to normal courtesy of the Bem, a race of aliens who had developed a device known as the De-Robotizer and used it on the Mobians. Only Jules, Chuck's brother, remained unchanged, due to the fact that his De-Roboticization would result in his death due to injuries. Chuck worked night and day for some time in hopes of finding a way to restore his brother to normal, but in the end it was Jules himself who stopped him, refusing to let Chuck continue to push himself beyond his endurance.
After the Xorda
Following the Xorda's failed attack and Sonic's return from space, Jules and Bernie continued to be the parents Sonic lacked for years and made sure Sonic was well fed and attended school. Bernie had to be reminded by Jules however that Sonic had grown up in their absence.
Chuck however became a member of the main group of Freedom Fighters. He served as a technical expert, befriending Rotor Walrus and working with him under Max's orders to build an elite unit of Metal Sonic Troopers, robots designed to defend Knothole after Sonic's apparent death. Upon Sonic's miraculous return, Uncle Chuck was the first relative to greet him, sharing a warm embrace with his nephew before sending word to Sonic's other family and friends.
Jules later confronted Scourge the Hedgehog (Sonic's Anti Mobius counterpart) when he attempted to beat up Sonic in his sleep. Jules was quick to insult Scourge, stating that because Mobius was full of heroes, their universe must be full of cowards. Scourge revealed to Jules his history with his father, and how Moebius had been a peaceful place until ten years after the Great Peace when everything stagnated and went into decline, at which point Scourge "woke it up". Scourge then proceeded to threaten Jules, but the Robian simply stood up to him and pointed out he was a veteran of the Great War, and would not go peacefully, adding that while Scourge might not miss his father, he was certain that Sonic would if he tried to kill him. With those words, Scourge left Sonic's house, crying due to what Jules had said.
After Scourge and the Suppression Squad were defeated, Chuck was present at Sally's trial for treason being held by the Council of Acorn.