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2.0 and Prior


The Smileys are a seemingly innocent organization within Los Santos. But underneath lies a darker secret. A secret that only nightmares are made of.

Origins of the Smile

The Smileys were once a gang in Carcer City, within Darkwoods Penitentiary for the criminally insane. They were one of many gangs within the prison bred for the purposes of creating death, quite literally, for the director of the Prison, Lionel Starkweather, a snuff film producer.

Death Row inmates would be tasked to kill members of the Smileys and other gangs in order to not only earn their freedom but to give 'The Director' footage of all the murder and mayhem that they would cause on their pathway to freedom.

But most of them died. Until the day that 'James Earl Cash' not only killed his way through Darkwoods but managed to CHAINSAW 'The Director' before making his escape, and while blowing a hole in the prison, allowing the inmates of Darkwoods to carve an entirely new path.

Entry into Los Santos

After their escape, the leader of the Smileys, Kenneth Jesperson AKA Mr. Smiley entered Los Santos with an entirely new goal and an entirely new method of creating future Smileys. Gone were the days of easily manipulated insanity, as Mr. Smiley had to reconfigure his whole philosophy in order to recruit people into his newly growing "family". Anybody can be a Smiley. But are you prepared to take a step further?

The Pins

The Smiley face pins, hand crafted by Mr. Smiley himself, are a catalyst to becoming an 'always-happy-every-day-citizen'. When you are given the pin, you are a Smiley forever and always. Although your life may not change much, the pin is a metaphor for protection in the eyes of the Smileys. The pin may also just be the starting point for those who wish to take their participation within the group to the next level.

The Song

In order to Associate or become a Full Member of the smileys, you must also sing the song of the Smileys. The song is called 'Smile', originally an instrumental piece in the Charlie Chaplin film 'Modern Times' but later given lyrics by Nat King Cole, and re-popularized by Jimmy Durante (The version that Mr. Smiley bases his initiation off of).

Though, sometimes the song is not sung, which begs the question the validity of some members, though only associating with the Smileys on a base level isn't nearly as important as those who want to take it a step further.

The Current Look

The Look of the 'New' Smileys, with the exception of Mr. Smiley himself, and any original Smileys from Carcer City, black and yellow, similar to Mr. Smiley's own face ma- I mean, FACE. But slightly more refined.

Although occasionally, in order to remain COMPLETELY anonymous, sometimes they will employ a more mysterious look to dissuade those who may think that the Smileys are responsible for something.


Although, the current goal seems mostly ambiguous, the Smileys wish to bring into their fold specific individuals of a specific repute. Anyone who joins can be shepherded into the darker impulses, however the Smileys TRULY want 'Visionaries' who wish to paint the city in blood and tears. No Robbing. No stealing. Only artistry in the guise of murder.

Those who DO NOT smile and who attack the PROTECTED citizen members of the Smileys will be destroyed. All the frowns in Los Santos will be turned upside down, through love... or pain. Make your choice.

But even through the fear and sorrow, just remember to smile. Always Smile. :)

Main Goals

  1. We need Visionaries!
    Find out who in the city is a “Visionary” (Serial Killer) and attempt to offer guidance or a home to help and ensure that they can complete their work whilst also being able to aspire to a family in their off-time. These people DO NOT have to be considered Smileys (given a pin or what-not) but are integral to the overall goals of the Smileys. They are our “clients”.
  2. We create Visionaries
    For those in the “New Blood” who wish to indulge, we shepherd and mold them into their own little artist, so that way, if they have a “vision” of their own they want to create, we can give them the tools and the confidence they need in order to complete that vision. We give them home on their way to independence.
  3. We Can Take The Heat
    The Smileys as a collective, have taken quite a bit of some heat of late. If you feel like the Police are getting close to you on your own independent project, we can help create just enough doubt in their eyes to make them believe that it was US who did it and not necessarily YOU.
  4. We Kill Our enemies
    Our enemies are vast, and our needs strong. There is a list, and on this list is growing number of “frowners”. These frowners have done a disservice to our Family. Only together, can the collective handle these threats, from those who attack us, to those who betray us. As much as there is a list of those who we DO NOT attack at any time, there are those on the opposite list. If you are bold enough, if you are strong enough, we want your help to take down these targets, whether temporarily or permanently.
  5. We Protect Our Family
    As difficult as it tends to be in a city as dangerous as this, the list of those who are involved in our activities and those who are NOT involved in our activities is important to us. If you want us to kill someone for you, we will do so. If someone has wronged you, we will fight back against them for wronging you. However, the “innocents” on the list are to be watched over and protected from the dangers of Los Santos. We. Do. Not. Attack. These people. And we expect the “clients” to adhere to the same.
  6. Murder for Hire/Or Just murder because.
    If you’ve heard of us, and you find us. Maybe we can kill for you, if you want it done. Just give us the fine details and we will see what we can do for you. 😊 …Payment? Possibly. Enjoyment. Hell yes!


  • The Smileys are based on the gang of the same name from the 2003 Video Game 'Manhunt'.
  • They DO exist within the GTA lore as Manhunt takes place in the same universe.

Smileys Member Roster