Face Claim/Appearance: 
Name: The Riddler
Age: Late 60s
Gender: Male
Canon: Batman: The Enemy Within
Main Thread or Sandbox: Main Thread
Personality: The Riddler was intellectually gifted, but very brash and arrogant, enjoying beating his opponents and believing himself superior to both his victims and pursuers. He also appeared to be deranged, enjoying seeing his victims scared or horribly injured. He also lefy elaborate clues and puzzles behind at his crimes, believing that nobody would be able to figure them out, something which he was proven incorrect on more than one occasion. He was also willing to kill innocents or risk their lives, as seen in his order to kill a hostage to distract Batman.
Equipment:
Costume: Riddler's costume consisted of a dark green suit jacket, a purple shirt, a green tie, dark green trousers and a pair of black leather shoes. To hide his identity, he would also wear a green domino mask and a hood, the latter of which seemed to be sown to his suit jacket. Riddler also wore a golden question mark on his left lapel and black gloves, to prevent him from leaving evidence that could lead to the authorities learning his identity. It is unclear how much protection he wore, but it is known that he had equipped a device that neutralized Batman's Bat-Stunners during their final confrontation.
Cane: Riddler would carry a golden-topped black cane during his crimes, which he used as both a weapon and a tool during his crimes. The top of this cane was stylized as a question mark, though the inside of it was sharp enough to cut human flesh. Riddler would use this as a method of execution of his victims and within combat with his opponents, using the hooked edge to grab at his enemies and objects to use in combat. The hook could also act as a grappling hook, with a button to detach and fire it at specific objects. This also came with a pulley system to pull the Riddler towards his target. The cane also had a multitude of different buttons on it, which could act as transmitters to activate or operate devices and contraptions, such as explosives and his death traps.
Puzzle Boxes: Riddler would often leave these boxes at his crimes, believing that his pursuers would not be able to solve them. These would often consist of elaborate puzzles, including riddles and methods to reshape them, and clues to his plans. Riddler would also place advanced circuitry within them for the purpose of challenging his opponents, such as one where the person had to manipulate waveforms to access their next clue.
Murder Boxes: Riddler would use death traps (or "murder boxes", as other people called them) to either taught his victims or challenge his opponents. These would consist of many different machines or devices, including controllable saw blades, sonic blasters and a multitude of different devices, most of which he made himself. One such was used on Rumi Mori, where he was trapped within a small glass chamber and his fingers were removed for each time he got the solution to a riddle wrong. Another trap, set for Batman, forced the vigilante to solve a puzzle whilst coping with a sonic blast if he got a riddle right, or killing an Agency agent if he refused or got it wrong.
Quotes
Attributes: Riddler possessed great inteligence, having a vast knowledge on riddles, which he used to his advantage to both intimidate, confuse, and torture his enemies. Despite this, his arrogance, along with his obsessions led to his downfall at the hands of Batman, and his eventual murder by Tiffany.
Biography: Riddler began his criminal career in Gotham, during the years it was controlled by Thomas Wayne, Carmine Falcone, and Mayor Hamilton Hill. He terrorized the city for some time, during which the trio gave him a personal berth to operate out of. However, in the midst of his criminal career, Riddler disappeared so suddenly that many believed he had died.
In reality, Riddler had been recruited by the Agency into their scientific division, SANCTUS. During his time there, he helped research for many of their top secret projects, including the experimental LOTUS virus. After multiple failed tests, Riddler was infected with the virus in an accident and was expected to die. Instead, he survived and was physically enhanced by the virus. However, his brain's chemistry was severely damaged and caused him to develop multiple mental disorders, including Obsessive Compulsive Disorder and Narcissist Personality Disorder.
Riddler was kept within the confines of SANCTUS for years, constantly monitored by their scientists hoping to study LOTUS's effects. Eventually, he was able to escape the organization and fled the labs, though installed a backdoor into their network to ensure he could access their files. With this, Riddler planned to expose both SANCTUS and the Agency as revenge for the experimentation. He also planned to regain his place as Gotham's greatest costumed criminal and rule the underworld.
Following his escape, Riddler built up a small criminal organization of his own and began operating internationally. During this time, he became acquainted with Selina Kyle/Catwoman after recruiting her for a heist. Riddler became a frequent contact to her, during which he seemed to show a kinder nature. He also acquired a personal barge called the Lady of Dublin, though it is possible Riddler gained it before his Agency employment.
Riddler heard tales of the Santa Priscan criminal mastermind Bane, who he believed could be a member of his growing numbers. To achieve his trust, he allowed himself to be captured and taken to Peña Duro prison, where he was being held. Shortly after being captured, Riddler orchestrated a mass breakout and murdered the warden. Though it gained Bane's trust, the breakout gained the Agency's attention, leading Amanda Waller to authorize a search for Riddler. Agents constantly followed Riddler to many counties, but he was able to escape them each time. During an encounter in Sudan, the Agency came close to capturing Riddler, but he was able escape.
Some time after the Children of Arkham's defeat, Riddler returned to Gotham with Bane at his side. Together, they recruited new criminals Victor Fries/Mr. Freeze, Harleen Quinzel/Harley Quinn, and former Arkham patient "John Doe" into their organization. Calling themselves the Pact, Riddler christened himself their leader and finalized his plan to attack SANCTUS. In return for their assistance, he promised each member access to LOTUS to cure various ailments they or their loved ones suffered, though hid the psychological effects. The group accepted the offer, though only John Doe refused (due to his own interests). Needing her help, Riddler also asked Catwoman to join them but she declined.
During this time, Riddler heard stories of Batman and his reputation in the city. Seeing him as competition and against the wishes of his fellow members, Riddler decided to murder the Dark Knight to make his return known in a spectacular fashion. For this, he allowed the Agency to track him down and bring their operatives to Gotham, including Waller. Setting himself up in an East End water tower, Riddler recruited local criminals in Gotham, including Eli Knable. Through arms dealer Rumi Mori, he gained access to radio signal-guided homing missiles. After creating a targeting signal, Riddler planned to hack into the agents' phones and install it onto them, guiding the missiles to their location. After Mori bowed out after learning his scheme, Riddler set up plans to murder the arms dealer in retribution and prevent him from leaking the plans early.
Name: The Riddler
Age: Late 60s
Gender: Male
Canon: Batman: The Enemy Within
Main Thread or Sandbox: Main Thread
Personality: The Riddler was intellectually gifted, but very brash and arrogant, enjoying beating his opponents and believing himself superior to both his victims and pursuers. He also appeared to be deranged, enjoying seeing his victims scared or horribly injured. He also lefy elaborate clues and puzzles behind at his crimes, believing that nobody would be able to figure them out, something which he was proven incorrect on more than one occasion. He was also willing to kill innocents or risk their lives, as seen in his order to kill a hostage to distract Batman.
Equipment:
Costume: Riddler's costume consisted of a dark green suit jacket, a purple shirt, a green tie, dark green trousers and a pair of black leather shoes. To hide his identity, he would also wear a green domino mask and a hood, the latter of which seemed to be sown to his suit jacket. Riddler also wore a golden question mark on his left lapel and black gloves, to prevent him from leaving evidence that could lead to the authorities learning his identity. It is unclear how much protection he wore, but it is known that he had equipped a device that neutralized Batman's Bat-Stunners during their final confrontation.
Cane: Riddler would carry a golden-topped black cane during his crimes, which he used as both a weapon and a tool during his crimes. The top of this cane was stylized as a question mark, though the inside of it was sharp enough to cut human flesh. Riddler would use this as a method of execution of his victims and within combat with his opponents, using the hooked edge to grab at his enemies and objects to use in combat. The hook could also act as a grappling hook, with a button to detach and fire it at specific objects. This also came with a pulley system to pull the Riddler towards his target. The cane also had a multitude of different buttons on it, which could act as transmitters to activate or operate devices and contraptions, such as explosives and his death traps.
Puzzle Boxes: Riddler would often leave these boxes at his crimes, believing that his pursuers would not be able to solve them. These would often consist of elaborate puzzles, including riddles and methods to reshape them, and clues to his plans. Riddler would also place advanced circuitry within them for the purpose of challenging his opponents, such as one where the person had to manipulate waveforms to access their next clue.
Murder Boxes: Riddler would use death traps (or "murder boxes", as other people called them) to either taught his victims or challenge his opponents. These would consist of many different machines or devices, including controllable saw blades, sonic blasters and a multitude of different devices, most of which he made himself. One such was used on Rumi Mori, where he was trapped within a small glass chamber and his fingers were removed for each time he got the solution to a riddle wrong. Another trap, set for Batman, forced the vigilante to solve a puzzle whilst coping with a sonic blast if he got a riddle right, or killing an Agency agent if he refused or got it wrong.
Quotes
Attributes: Riddler possessed great inteligence, having a vast knowledge on riddles, which he used to his advantage to both intimidate, confuse, and torture his enemies. Despite this, his arrogance, along with his obsessions led to his downfall at the hands of Batman, and his eventual murder by Tiffany.
Biography: Riddler began his criminal career in Gotham, during the years it was controlled by Thomas Wayne, Carmine Falcone, and Mayor Hamilton Hill. He terrorized the city for some time, during which the trio gave him a personal berth to operate out of. However, in the midst of his criminal career, Riddler disappeared so suddenly that many believed he had died.
In reality, Riddler had been recruited by the Agency into their scientific division, SANCTUS. During his time there, he helped research for many of their top secret projects, including the experimental LOTUS virus. After multiple failed tests, Riddler was infected with the virus in an accident and was expected to die. Instead, he survived and was physically enhanced by the virus. However, his brain's chemistry was severely damaged and caused him to develop multiple mental disorders, including Obsessive Compulsive Disorder and Narcissist Personality Disorder.
Riddler was kept within the confines of SANCTUS for years, constantly monitored by their scientists hoping to study LOTUS's effects. Eventually, he was able to escape the organization and fled the labs, though installed a backdoor into their network to ensure he could access their files. With this, Riddler planned to expose both SANCTUS and the Agency as revenge for the experimentation. He also planned to regain his place as Gotham's greatest costumed criminal and rule the underworld.
Following his escape, Riddler built up a small criminal organization of his own and began operating internationally. During this time, he became acquainted with Selina Kyle/Catwoman after recruiting her for a heist. Riddler became a frequent contact to her, during which he seemed to show a kinder nature. He also acquired a personal barge called the Lady of Dublin, though it is possible Riddler gained it before his Agency employment.
Riddler heard tales of the Santa Priscan criminal mastermind Bane, who he believed could be a member of his growing numbers. To achieve his trust, he allowed himself to be captured and taken to Peña Duro prison, where he was being held. Shortly after being captured, Riddler orchestrated a mass breakout and murdered the warden. Though it gained Bane's trust, the breakout gained the Agency's attention, leading Amanda Waller to authorize a search for Riddler. Agents constantly followed Riddler to many counties, but he was able to escape them each time. During an encounter in Sudan, the Agency came close to capturing Riddler, but he was able escape.
Some time after the Children of Arkham's defeat, Riddler returned to Gotham with Bane at his side. Together, they recruited new criminals Victor Fries/Mr. Freeze, Harleen Quinzel/Harley Quinn, and former Arkham patient "John Doe" into their organization. Calling themselves the Pact, Riddler christened himself their leader and finalized his plan to attack SANCTUS. In return for their assistance, he promised each member access to LOTUS to cure various ailments they or their loved ones suffered, though hid the psychological effects. The group accepted the offer, though only John Doe refused (due to his own interests). Needing her help, Riddler also asked Catwoman to join them but she declined.
During this time, Riddler heard stories of Batman and his reputation in the city. Seeing him as competition and against the wishes of his fellow members, Riddler decided to murder the Dark Knight to make his return known in a spectacular fashion. For this, he allowed the Agency to track him down and bring their operatives to Gotham, including Waller. Setting himself up in an East End water tower, Riddler recruited local criminals in Gotham, including Eli Knable. Through arms dealer Rumi Mori, he gained access to radio signal-guided homing missiles. After creating a targeting signal, Riddler planned to hack into the agents' phones and install it onto them, guiding the missiles to their location. After Mori bowed out after learning his scheme, Riddler set up plans to murder the arms dealer in retribution and prevent him from leaking the plans early.