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Kenneth “Mr. Smiley” Jesperson is a character role-played by mrwest16



When he first came to Los Santos he was wild, completely unhinged, and prone to bursts of pure anger on the basis of people referring to his 'Face' as a mask or people using his 'birth name'. For all intents and purposes, he is a psychopath with social-anxiety disorder.

However, after much therapy and intense acclimatization to his new environment within the city of Los Santos, he has calmed down to a point that he now considers himself a 'Productive Member of Society'. However, that is an obvious guise to the fact that the therapy he received had the OPPOSITE effect on him, and helped him become a much more clever, clear, and focused Psychopath.

Generally, he is actually VERY friendly to people. And, despite his appearance, and vocal demeanor, he gives no real indication that he wants to hurt anyone. Because of this, lots of regular citizens think he's a great guy to have as a friend.

Though he still often has bursts of anger towards those who attack other Smileys and he has no qualms with taking out a knife to assert dominance.

Despite this, he has extreme loyalty to his fellow Smileys, almost to a fault. And even has the capacity to love and show love to the people he considers his friends... and slaves.

Background Information

Born in Hell, otherwise known as ‘Carcer City', Kenneth Jespersen lived most of his life under the rigors of perpetual war between rival street gangs of whom have long since forgotten the reason for their plights of conflict. Raised by neglectful parents who were as equally part of the problem as any two-bit criminal, Kenneth would have a short-lived childhood as he was, at the young age of thirteen, thrown into ‘Darkwoods Penitentiary’, a prison for the criminally insane, for reasons currently unknown.

He would join the biggest gang in the prison, known as the ‘Smileys’, a group of lunatics where psychopathy is a constant among other things. Murder, Torture, Cannibalism, etc. etc. the Smileys were at the forefront of all these things and they took pleasure in all of it. As time trudged forward, Kenneth would no longer acknowledge his birth name, and he would put the mask of the Smileys on his face, but little did he know, this mask would become part of him, almost literally and figuratively.

As the years went on, he would assume the name ‘Mr. Smiley’ and become the leader of the Smileys, tasked by the ‘The Director,’ Lionel Starkweather, to help death row inmates complete their task of creating “snuff films” for sale in the black market. The gangs of Darkwoods, and most notably the Smileys, were created to ‘hunt’ these death row inmates with whatever weapons they could acquire and fight them to the death but not before filming the deadly confrontations. ‘Mr. Smiley’ was one of the few of these hunters who survived the confrontations having claimed over 200 victims, although not all of them were because he was made to. And not all of them were in the prison.

Now that ‘Mr. Smiley’ is a free man, what will he do next?

'The Scarecrow'

Inspired by the lore of the same name, Scarecrow was the nickname that Smiley originally went by before adopting the 'Mr. Smiley' persona. He would walk around the prison with a sack on his head, looking like a scarecrow, killing indiscriminately anyone who would even look at him the wrong way. He would speak in garbled mumbles but would eventually find his voice again once the other Smileys started to look to him as a leader.

In Los Santos, the moniker was resurrected in order to create a "smokescreen" to divert attention away from 'Smiley' activities and to confuse police into thinking there was more than one killer active at any given time despite all the bodies dropped being essentially from the same person or persons. 'Scarecrow' was meant to invoke fear in targets to the point of mentally manipulating the victims to make them easier prey for the final attack, but also as a means to perhaps capture more than one victim for those who wish to save them.


He was on a mental evaluation hold at Parsons Rehabilitation Center, but was released on February 26, 2020.

#CarcerWorld (3.0)

After his release from Maximum Security prison under mysterious circumstances, Smiley was already hard at work plotting and planning his next scheme.

Carcer World is a movement. Before, the killers who joined The Smileys were mostly independent but would come together under one roof to do 'jobs' as well as assist clients, but with the 'Carcer World project' the intent is to TAKE POWER over the serial killer element within the city of Los Santos.

But this is not subjected to simply serial killers. But assassins, mercenaries, and other 'underbelly' figures who do work outside the traditions of typical criminality.

Named after his home city of Carcer, Kenneth believes that bringing a slice of home to Los Santos would do it some good, as the nature of Carcer City is just that... a hellhole where blood, death, and anarchy run rampant.

In order to spread the message of Carcer World, Kenneth would order his Smileys to drop a calling card, make victims tweet out #CarcerWorld, or carve into victims to spread awareness and the message of the movement. Although Kenneth would prefer targeted attacks against 'serials' or other significant individuals within the city, but in order to make an omelet, you gotta crack a few eggs. :)

'Make Me Smile' Project (3.0)

An expansion of Kenneth's work at the end of 2.0, he implemented brainwashing techniques that would essentially enable him to 'create' new Smileys who would listen to his every command. The Process would involve months long 'education' in order to implement. Removing essential elements from a person's life before slowly reintroducing it invoking a certain level of "Stockholm" as well as implementing physical and mental tactics of an indescribable nature.

Topping it off with a dash of hypnotic suggestion. So far, the only one to receive the treatment has been Brett Maxwell at the hands of Rick Locke.

Later, Kieran Felix White, Harleen Quinzel, and May Flowers would be added to the family through the tactic.

Rick Locke himself would later be placed into the 'Project' and reconfigured into Kai Locke, as perpetrated by his child May Flowers (Fauna Locke).

Smiley always wanted to create a family, and now he can TRULY make the family he always wanted in the image he sees them in.

'The Fear Initiative' (3.0)

Coming Soon. :)


Kenneth, after being incarcerated, was forced to partake in the production of many snuff films, so as the years went on, his craft as a "Performer" allowed him to come up with and BECOME several different roles or identities as it were. But NOT different Disassociated identities but simply identities created through the art of 'Method' acting. And he took the method very seriously to the point that he would NEVER break character depending on the role he was portraying, regardless of whether the camera was rolling or not.

Here are some of his such "Roles":

Mr. Smiley

The moniker given to Kenneth Jesperson to signify his status as the leader of 'The Smileys'. Essentially, an amalgamation of all of his "Identities". This role was used as more of a 'Bit' part in the snuff films as where he could have easily been any random Smiley who was hurt, maimed, or possibly even killed by whoever the protagonist of the film was. However a good chunk of the time, he would be the "Producer" of the film and he would place other Smileys and gang members in their proper locations for when filming was set to occur. Kenneth sees Mr. Smiley as his true self, though there is some debate about this as another one of his "Roles" came before.

In Los Santos, Mr. Smiley is his most known persona and the persona he has found himself most comfortable attributing to. A persona he once became so immersed in that he not only saw the mask as his face, but also felt ALL the pain he had ever received from the violence of his past coming back to haunt him the moment he would 'break' character or try to break character by removing his mask or any article of clothing. He has since overcome this and can now go in and out of the persona at any moment of his choosing without fear.


When Kenneth was first placed in Darkwoods, he lost most of his ability to speak coherently and decisively. Along with Barry, Fug, and many other Smileys, Kenneth was bestowed the name 'Scarecrow' because he would wear a very distinguishing sack on his head and garb that made him look as such. Of all the Smileys, he was perhaps the most deadly and "trigger" happy when it came down to killing. A truly fearful sight to behold to the point that even his own people feared him for his callous and relentless nature. Scarecorw never played a specific role in any film, he was seen as more of a dark passenger who ensured that the films were produced without flaw and that the Smileys would stay in line.

As things stand presently in the city of Los Santos, the role returned. With the intent of it being the most merciless of all his roles and personas. Someone who does not care who he hurts or kills, as where Mr. Smiley can at times be ruled by compassion, Scarecrow is the opposite. His speech patterns are almost completely different as well as done as a means to instill a certain level of monotone fear into his victims before going for the kill. He spent months playing the role with Sydney before enacting his final judgement upon her and her friends.


Kenneth is who he was before Smiley, before Scarecrow, before any of his other roles or personas. As Kenneth Jesperson, he is calm, collected, cool, and frightening in terms of how he presents himself at times as it is so RADICALLY different than what you would see in his Mr. Smiley role and even to an extent his Scarecrow role. For a time he would put on a very, very fake sounding voice that was clearly meant to be his 'Normal' citizen voice but for those who were paying attention, they could tell this was fake. Eventually, he would find his normal speaking voice without having to 'put on a voice'. The only time he was referred to as Kenneth when he was in Darkwoods was right before his full incarceration, Lionel would call him 'Kenny boy' but he would quickly forget and discard this name after going through, the 'process' of becoming a 'Smiley', and a performer in Starkweather's films.

If Mr. Smiley is meant to be Kenneth at his most real, accentuated self, Jesperson is the exact opposite in every way.


The Tramp was, as is described, a homeless man who loved to drink alcohol. He was perhaps Kenneth's greatest role. After having been cast in a film as the lead he was finally given full creative freedom to sculpt his own path and dish out the pain to others that was often times dished out to him firstly.

The film he starred in was called 'The Tramp Who Knew Too Much' a movie that was different than a lot of Starkweather's other directorial efforts. A film with heavy dialogue and a much more refined plot and character motivation which made the film seem like more of an art piece than anything else. Unfortunately, the movie didn't sell very well on the black market due to its less of a focus on the blood and guts and more of a focus on artsy-fartsy crap as Starkweather would describe it.

Kenneth would portray the Tramp character again in another film, but the role was reduced to a glorified cameo where he was a helpless man who needed to be saved from The Innocentz, of which greatly upset him.

It was partially because of this reason that Kenneth brought the character back in Los Santos to begin a de-facto sequel that would redeem the Tramps name as a threat to be reckoned with.

*Before coming to the city, he claims to have killed 200 people in Carcer City making his kill/attack count at 270*

List of Kills

  1. Lunar Tranquillitatis (Stabbed)
  2. Skinny Pete (Stabbed)
  3. William Williamson (Stabbed)
  4. Jake Frasteafrom (Stabbed)
  5. Flop Dugong (Hammered)
  6. Larry Dickerson (Stabbed)
  7. Regina Bunny (Hammerd)
  8. Sydney Bearmont (Hatched)
  9. Takashi Morrimoto (Stabbed)
  10. Dougie Howzer (Hatched)
  11. Random Victim on a Jasper Cassette Tape (Hammered)
  12. Random Victim on Smiley's OWN Cassette Tape (Drilled)
  13. Thomas Dwayne (Stabbed)
  14. Arthur Ale (Hatched)
  15. Darlene Pickens (Stabbed)

(As The Tramp)

  1. Reginald Jones
  2. Steven Rich
  3. Elizabeth Duncan
  4. Damien Sharp (Alive)
  5. Mitchel Saltzman
  6. Leslie Poehler
  7. Tina Lemon
  8. Jacob Bennett | December 16, 2020
  9. Richard Bennett | December 16, 2020
  10. Mary Bennett | December 16, 2020
  11. Hayley Bennett (Alive) | December 16, 2020
  12. Sutter Kane (As part of the Legion Square "Demonstration")
  13. Carrie Black (As part of the Legion Square "Demonstration")
  14. Michael Strode (As part of the Legion Square "Demonstration")
  15. Nancy Krueger (As part of the Legion Square "Demonstration")
  16. Ryann Devereaux (Alive, As part of the final Manhunt) | January 19, 2020
  17. Jeffrey Bradley (Alive, As part of the final Manhunt) | January 19, 2020
  18. Bonnie Venture (As part of the final Manhunt) | January 19, 2020

(3.0 Kills)

  1. Betty Jax (Gun Shot)
  2. Daryl 'Bonez' Blood (Stabbed)
  3. Alexandra Yang (Stabbed w/Jocelyn Wade)
  4. Alberl Jonie AKA The Tower (Stabbed)
  5. Emma Levine (Stabbed multiple times, left for dead)
  6. Steven Hayes (Stabbed)
  7. Shirley Lemons (Stabbed)
  8. Posy Florian (Stabbed, throat slit)
  9. Cassandra Silverton (Hatcheted)
  10. Hanna Baker (Tortured, Carved into, and hit with an axe)
  11. Cara Lynn (Gun Shot)
  12. Keith Wanderlust (Stabbed)
  13. Kiki Pendragon (Stabbed, Sliced Stomach)
  14. James Sarkoff (Intended to be brainwashed into believing he was Joshua Wade)
  15. David Sear (Intended to be brainwashed into believing he was Kenneth)

List of Participated Kills

  1. Denis Menis
  2. Pogg Dann
  3. Arthur Yelton
  4. Frank Beans
  5. Ryan Hernandez
  6. Dakota Black
  7. Jeremy Rivet
  8. Boe Jangles
  9. Jerry Slime
  10. Stanley Stepper
  11. Savanna Skinner
  12. Mervin Potts
  13. Tessa Lamb

(3.0 Participated Kills)

  1. Father Dinke
  2. Delmon Homme (Directed from Phone)
  3. Josh(John) Levine (Watched him being drained of Blood from afar, by Honey Quickk)
  4. April Levine (Watched her being drained of Blood from afar, by Honey Quickk)
  5. Doctor Destructo
  6. Kai Leo
  7. Francis Angel Luis
  8. Cora Katz (Wasn't there when they were killed but provided them for Bree McNab and Percy Perkins.)
  9. Richard Kuklinski (Wasn't there when he was killed, but provided him to The Damaged.)

Relationships (Most of these relationships are 2.0 Centric)

August Vakarian

A very close friend to "Mr. Smiley" of whom he met while they were both in Parsons Rehabilitation Center, they instantly clicked and have remained close ever since. Although they seem to have different ideas on how to approach "criminal" activity and will sometimes even criticize each other for recklessness or a lack-thereof. They have a pseudo-sexual-abusive, but consensual, relationship where often times when she asks him to hit her, he will, due to her masochistic nature. And sometimes even allowing her to hit HIM in order to help treat her schizophrenic tendencies to see things that aren't there. Smiley was one of the first people to say that he LOVED August when she brought up the 'L' word to him, although he does not have the capacity for love in the romantic sense, he still loves her as a friend and would never harm her, unless she asked for it.

Tobi Argent

After Jaden's death, Tobi Argent essentially became the new "information guy" in regards to collecting and dispersing critical information to Smiley and friends. But as time would go on, Tobi would become one of Smiley's oldest and best friends in the city, being one of the only people, other then Smiley himself, to still be alive and REMAIN on good terms with him throughout. Together they weathered the storm of The Coven, Alexandra Moroz, the fracturing sanity of Chasity Dawes, and the consequences of Imperium. Although they have certainly had a rocky relationship at times, Tobi and Smiley remain good friends to this day, despite slightly divergent paths.

Tessa Lamb

One of the first few people that Smiley met when he was released from Parsons who treated him like a normal person, despite his clearly lunatic demeanor. Part of it he believed was to due to the fact that he assumed she was just pretending to accept him so he wouldn't become angry with her and perhaps hurt her. But a few conversations after he NAILED his driving test and gave her a Smiley face pin, he quickly understood that her capacity for acceptance was far greater than most as he even confided in her the fact that he killed over 200 people prior to entering Los Santos. And she simply told him "that number doesn't define you either. I just wanted you to know that.". This relationship has even gone as far as Smiley ACTUALLY admitting that he is wearing a mask to her. Something he would NEVER do, traditionally. They have remained friendly ever since, and Smiley tries to look out and "protect" her as much as he can. Whenever he can.

Recently, she had begun to learn that Smiley was dangerous to be around, so he called her out to the fishing dock up north and they had a discussion in which he would reveal a ton of information about the 'Underground below the Underground', and this conversation led to Tessa revealing herself as 'Mary Wolf' to Smiley. This would make Smiley the third or fourth person in the entire city to be aware of 'Mary Wolf' who WASN'T one of her victims, opening an entirely new chapter in the Smiley/Lamb dynamic.

Johnathan Wright

The relationship between Johnathan and Smiley has been a complicated one. Although Wright seems to believe he has figured Smiley out, the tables have certainly turned into more grey directions. What started as a semi-antagonistic relationship, became a "friendly" relationship on the basis of him being one of the only therapists that seemingly understood Smiley and accepted him for what and who he is. Smiley made Johnathan a smiley, however, his lies the night that Smiley was detained and placed into Parsons forever put a mark on that relationship that Smiley has been waiting ever so patiently to repay. Though he has no personal issue with Wright and even will go as far as to say that he very much LIKES the man, and will protect the man when the need arises, his punishment has alluded him and their chess match of who will upset the other first has continued on-and-off ever since. But the question is, who will get that checkmate first?

Victoria "Vivi" Veine

Although they have not known each other long, Vivi and Smiley hit things off rather quickly. Being one of the few people to instantly correct herself once she mistakenly referred to Smiley's face as a mask. Up until the night that Smiley had a meeting with 'The Coven', a group of medically diseased vampires, they had more of a passing relationship. But after Smiley asked her for a favor to sit-in on this meeting and act as a sort-of henchmen to keep the vampires from attacking him, he would later learn that there was more to this woman than met the eye as she would later introduce him to a man wearing a mask, dressed in black. A man as mysterious as Smiley himself. Vivi and Smiley wish to keep in contact to see where this rabbit hole takes him as time trudges forward.

Jaden Sparks

Jaden was one of Smiley's first friends in the city after being released from Parsons. When they first met, he would be intentionally vague toward Smiley, and would call him randomly on the phone/watch him from a distance without revealing how he received his number. Although Smiley would quickly, and correctly, guess that it was August who gave it to him he still kept him guessing for a while. Both men seemed to have a lot in common and Jaden would help gather information for Smiley in an attempt to help build-up his "growing family". Although Smiley never truly understood why Jaden wanted to help him, and one of the final conversations they had before his untimely death went something like this: "Why are you helping me?" and Jaden responded with "Because I like your cause." Even though Jaden didn't seem to fully understand the cause, he wanted to help build it and see to it's goal. And, after his death, that cause has grown larger than Jaden could have possibly imagined.

Hemet Nesingwary

The first "true" serial killer to be recruited into the Smileys as a pesudo-member who shows up usually only when Smiley needs him to, or vice versa. Smiley saw an ad in the Yellow Pages about a "Hunter" offering his services while in Parsons. Smiley would instantly ask him if his hunting involved 'human' hunts, and Nesingwary almost, without hesitation, admitted to everything. Although seemingly, they have different ideas about their plights of murder, thus far, there has been a fairly good business rapport between the two enabling one to help the other if need be. Although, this relationship may be doomed as some of the people on Hemet's list are people that Smiley protects... so what will happen as this relationship continues?

Gemma "Emerald" Knight

Generally, a fairly new relationship in Smiley's pocket, initially, Smiley saw Ms. Knight as an enemy. That antagonism led to Smiley sending her an email with a video entitled ["I seeeee youuuuu" ] after having one of his Smileys, Nicholas Reyes, get bitten and drained of blood by her. Smiley wanted to destroy the ENTIRE Vampire Coven but after some convincing from Jaden, Smiley would settle down on this mentality and open up talks with the vampires instead, which led to Gemma offering to join the Smileys in exchange for August joining The Coven. It's a fresh relationship, but so far, a friendly one after a month of a sort-of-cold war.

Flop Dugong

What started as an innocent induction into the Smileys, like any other person brought into the group would later become a game of cat and mouse, and no one would ever have expected Flop, everybody's "fellow Dugong" to become one of Mr. Smiley's greatest nemesis'. But before that, the relationship was very positive, Flop would show Smiley around town and they would hit it off rather well with very friendly banter. For a time, Flop may have even once been considered one of Smiley's favorites similarly to Tessa Lamb, however fate would be against this as once Flop began investigating the 'Scarecrow' stalkings of Sydney Bearmont, Smiley took action and left Flop for dead out at the docks.

Ever since then, Flop has been uneasy around Smiley, and Smiley has been uneasy around Flop. And they have continued the game of 'cat and mouse' ever since, both wanting the other dead.

Sydney Bearmont

A very close friend of Johnathan Wright, based on the plans of August Vakarian, Smiley was able to investigate who was close to Johnathan in order to facilitate the 'Scarecrow' project in which he was meant to bring both her and another individual to a specific location in order to make Johnathan "choose" who would live and who would die to challenge his philosophy on life of "everyone being equal" through his eyes.

Smiley would befriend Sydney, learn more about her, and even eventually initiate her into the Smileys. And once the plan started to take shape, Smiley would begin placing threatening phone calls to her to invoke fear into her and mentally manipulate her in order to easily pick her up for the final act against Johnathan. However, things have gone quiet on the western front, and Smiley and Sydney have not spoken since suspicion of him reached a fever pitch. However, that may soon change.

Andi Jones

While in Parsons, Smiley called Andi on the Yellow Pages, who was offering pep talks because he felt sort of down on his luck due to the unending and lonely nature of Parsons. She introduced him to the concept of the Chicken Man and they have remained fairly close ever since. As with many people, she KNOWS who and what Smiley is, but instead of casting him aside she always actively attempts to change him and make him a better person, even if the end result is always the same. However, despite this, Smiley genuinely cares for her.

Regina Bunny

Smiley and Regina first met during his first stay in Parsons. She was emotionally down and out so August invited her out to the facility to meet with him and her. Living up to his name, he managed to put a Smile on her face and he would give her a pin. Fast forward a couple of months, that relationship would essentially end after Smiley found out she supposedly gave out information she wasn't supposed to give so he proceeded to give her the hammer treatment. However, recently, they have started to get close again as she is one of the few people that Smiley regrets hurting, and their relationship has even gotten to a point to where she MIGHT even adopt him as a son. A night and day thing brought on by the fact that Smiley was there for her the day that three of her fingers were chopped off by Denzel Williams and Carlos Sanchez. Much like Andi, she too wants Smiley to be a better person despite the obvious illusions against it.


  • He is known for wearing a smiley face mask, which he believes is his face.
  • He was previously an inmate at the Darkwoods Penitentiary, in Carcer City.
  • Mr. Smiley is based on "The Smileys" gang from the videogame Manhunt.
  • Often makes people sing 'Smile', a song by Nat King Cole/Jimmy Durante/Charlie Chaplin.
  • Does NOT like being compared to 'The Joker' or in this case, Jack Knaves.
  • His real name is inspired by real-life Serial Killer, Keith Jesperson, known as the "Happy Face Killer"
  • Is a huge fan of the Dragon Ball Franchise.
  • He quotes 'The Wondrous Boat Ride' from the film 'Willy Wonka And The Chocolate Factory' before a lot of his kills.
  • People often mistake him for Jasper Saxon and vice versa.
  • Inspired by Cut Content Character 'Kenneth Jesperson' from the aforementioned video game: Scarecrow... Scarecrow... Scarecrow....


  • "I just got out of parsons!"
  • "I'm a productive member of society now!"
  • "....Good." (In response to Sydney's fear of him)
  • "This is me underneath." (He reveals a horribly scarred, worn face)
  • "I felt responsible, I had to show it to you. I had to... to see the truth. Every time I take off my face, there's nothing but unrelenting pain. Unrelenting pain and misery... But I'm willing to endure the pain so you can see the truth. Because you deserve the truth, and nothing but the truth." (Upon first meeting Mary Wolf)
  • "There's so many people in The Smileys who are willing to complete visions. That's what I do, I try to 'complete visions'. I don't use the term serial killer because it's such a childlike term. I don't even consider myself one."
  • "I take it that... I'm not speaking to Tessa Lamb right now." (After noticing the change in Tessa)
  • "She will be immortalized. But she will not be immortalized… by you." (He says of Chasity, before stabbing Thomas Dwyane)
  • "Sydney Bearmont. The Day of reckoning is nigh. The Day of the Scarecrow is coming. Prepare yourself for Armageddon."
  • "I love you too, August..." (He says to her in Parsons)
  • "Poor guy, Apples!"
  • "We sound nothing alike!" (When people think he's Jasper Saxon because of similar vocal cadences)
  • "The Scarecrow is coming!"
  • "Smile every second, smile every minute, smile every hour..."
  • "Always Smile!"
  • "...Welcome to Creep Club."