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During his childhood, Randall had short hair, and didn't have glasses. He wore a striped-red jumper over a white shirt with red shorts.
As a teen, Randall had black-framed glasses and spiky hair, and wore a purple jacket over a purple shirt. He also had an orange ascot, blue jeans and black shoes.
He seemed to be friendly and nice, and very outgoing. In the past, he was described as reckless and headstrong. He had a strong desire to become famous as a teenager, due to his wish to not live in his father's shadow forever. It is also shown that he has a tendency to ignore what other people think every once in a while; for example, he disregards Angela's own wishes for him to stay behind in Stansbury and goes on a dangerous archaeological mission, and he is constantly dragging Hershel along with him on these missions. However, despite this, he is in no way a malicious person, and truly cares for his friends.
During his childhood, Randall was the son of a wealthy couple in Stansbury with Henry as his servant, whom he grew to think of as a friend.
One day, he witnessed Henry being scolded by a maid for playing with his toy and quickly rushed to defend him by giving the toy to Henry before pushing her out. Henry would treasure the toy for many years to come.
He was friends with a young Angela and Alphonse and together, including Henry, the four went on many adventures together.
At some point, during his teenage years, he and Angela were "romantically involved" "while in middle school" (as described by the "World of Professor Layton" artbook) and later befriended Hershel Layton, who moved into town later on.
One day, he discovered the Mask of Chaos after solving the riddle of the Norwell Wall and convinced Hershel to come with him to the Akbadain Ruins. Angela was opposed, fearing he'd suffer the same fate as her brother but eventually, he managed to convince her as well with Henry's help who stated that this would be his last expedition.
Unbeknownst to her, the reason he was doing this was to convince her parents that he could provide for her and ultimately accept him once he proposed to her afterwards.
Together, the two friends made their way down, solving puzzles and defeating mechanical mummies but once they arrived to the eight level, Randall triggered a trap, causing the floor to collapse below him where he fell. Before he did, Hershel attempted to save him but Randall was obstinate and instead, attempted to hand him the mask unsuccessfully.
Randall was saved by an underground river which carried him over to the tiny village of Craggy Dale where he was found and taken in by Firth. He was aided back to health by the villagers but due to his fall, he lost his memories.
Over the next 18 years, he would remain in Craggy Dale as a farmer.
At some point, he received a letter from Jean Descole detailing his life before he got amnesia, and asking him to don the disguise of the Masked Gentleman in order to perform "dark miracles." Regaining his memories from the letter, and believing that Henry had stolen everything he once had, he agreed for the sake of revenge. This began his reign of terror over Monte d'Or.
As the Masked Gentleman, he used a combination of stage tricks and accomplices in order to deceive people into believing his dark miracles were real.
His first dark miracle involved transforming several people into horses. The truth was that a bright flash of light momentarily blinded people as his accomplices were lead into alleyways, and horses with their clothing lead out. This gave the illusion that the people were transformed into horses.
His second dark miracle was making paintings in the museum come to life. The people in the paintings were painted using a special paint that vanished when exposed to air for a long enough time. The paintings were then stored in an airtight case and donated to the museum with special instructions to hang at noon. Accomplices that looked like the characters in the painting then came out of hiding to cause the illusion that the paintings had come to life.
His third dark miracle was sending letters inviting 13 people to an area, and having them burn to ashes; only to reappear fine at their homes later. He actually sent a second letter along with the first with instructions to not show it to the police, and to not actually leave their homes. He then had created mannequins that looked identical to the people (barring their clothes), and coated them in a flammable material. He set the mannequins on fire while the people were safely at home, causing the illusion that the people were burnt alive.
- Main article: Gallery:Randall Ascot
- Professor Layton, Jean Descole, Anton Herzen, Randall Ascot and Rufus Aldebaran are currently the only characters who are known to be able to sword-fight/fence.
- Randall, along with Layton, used to be a member of the fencing club as teens. He was the more skilled of the two.
- Towards the end of the game, Randall's mother can be seen in the cutscenes as an old lady, wearing glasses like those of Randall's.
- Randall once found an old coin during a dig, and he took it with him wherever he went to bring him luck. Before the expedition to Akbadain, he gave it to Angela as part of his promise that he would safely return.
- Randall claims to be a champion sprinter.
- Despite wearing glasses Randall has perfect eyesight and only wears them to mimic a famous archaeologist.
- The four stories at the Reunion Inn were based on his life and the lies Jean Descole told him.
- The five children who found treasure are meant to represent himself, Layton, Angela, Henry and Alphonse.
- The scholar represents Layton who seemingly left Randall like the dog in the story.
- The man who became rich represents Henry, the city represents Monte d'Or, and how the town decays represents how Henry allegedly didn't pay off his debt to Randall.
- The knight represents Randall and how he escaped the ruins, the princes and chancellor are Angela and Henry respectively.
- Randall's last name, Ascot, links in with his wearing of an ascot when he was a teenager. (However, it should be noted his surname in the original Japanese version is Ascad.)
- He is likely left handed as this is the hand he uses in fencing.
- In the Miracle Mask Collection there is a strange hint coin that has on it the Professor Layton seal, but with a "R" instead of the "L": the "R" could mean Randall.
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