Lollipop Guild (5e Guild)

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Lollipop Guild[edit]

We represent the Lollipop Guild
The Lollipop Guild, the Lollipop Guild.
And in the name of the Lollipop Guild
We wish to welcome you to our Land
~ Ballad of the Lollipop Guild

Small-sized males clad in all blue and carrying huge lollipops make up the infamous Lollipop Guild.

Inside the Lollipop[edit]

The Lollipop Guild is simply any male of a small-sized race that wishes to welcome people that visit their towns, cities, homes, or lands. The group has no formal leadership since all that is required of them is to sing their ballad to welcome people. Once the song is sung, they disperse and continue their business as usual. Members are typical joyful and smiling. No one feels welcomed by a scowl!

Goals of the Lollipop Guild[edit]

For all its existence, the Lollipop Guild has only ever had one mission: Greet newcomers with their song. By extension of this, the Lollipop Guild has been seen as cheerful and spreading happiness to others. Interactions with other guilds is usually minimal too and if pressed on the Lollipop Guild backs down from confrontation. They only want to bring glee and warm welcomes to others so hostility and violence is usually avoided.

Lollipop Guild Characters[edit]

Alignment: Usually neutral, often good
Suggested Races: any small-size
Suggested Classes: Bard

You might enjoy playing a Lollipop guild character if any of the following sentences describe you:

  • You enjoy welcoming others
  • You like to sing
  • You find joy in making others happy
  • You want to help others

Joining the Lollipop Guild[edit]

Membership is easy: Be short and happy! Sometimes small races can be tossed aside or looked down on and the Lollipop guild helps bring cohesion for all races that are short.
When you start adventuring, you'll find other places that have a Lollipop guild and you'll instantly be welcomed by your guildies. You may even find it fun to join in on singing with them and welcoming yourself!

Background: Lollipop Performer[edit]

Essentially a performer, you enjoy singing, dancing, and theatrical acts to welcome people. Your kind spirit makes it easy for others to get along with you and you're almost always willing to lend a helping hand. A long frown or a angry red face is nothing but an opportunity to help someone in your eyes.
Skill Proficiencies: Acrobatics, Performance
Languages: Choose one from Gnome, Halfling, or Dwarven.
Tool Proficiencies: One type of musical instrument
Equipment: Lollipop Guild attire & insignia, a musical instrument (one of your choice), a tinderbox, 10 torches, a belt pouch containing 10 gp

Feature: Smallfolk[edit]

You are recognized as an individual wanting to help others and do good. The cheerful reputation of your people proceeds you and there is no difficulty for you to find food and shelter for 1d4 nights, after which even the friendliest face becomes the visitor that stinks like fish.

Lollipop Guild Spells[edit]

Prerequisite: Spellcasting or Pact Magic class feature
For you, the spells on the Lollipop Guild Spells table are added to the spell list of your spellcasting class. (If you are a multiclass character with multiple spell lists, these spells are added to all of them.) The spells used by the Lollipop Guild are mandated to be used only to put smiles on people's faces, and can never be used for ill!

Level Spells
Cantrips guidance, mending
1st bless, ceremony
2nd calm emotions, aid
3rd daylight, beacon of hope
4th aura of life, aura of purity
5th wall of light, modify memory

Suggested Characteristics[edit]

Lollipop guild members are tooth-achingly sweet people. They are largely characterized on the side of benevolent emotions, though people who dislike optimists would find them nothing but annoying.

d8 Personality Trait
1 I tell myself every day that it's going to be a wonderful day.
2 I will never run away from a challenge!
3 I smile through rain or shine!
4 If I see someone crying, I can't help but go help!
5 When the going gets tough, I look for silver linings.
6 I hear that my smile is infectious.
7 Everyone is a viable friend!
8 Sometimes a good word is all someone needs to have a better day!
d6 Ideal
1 World Happiness. I want to spread smiles all around the world! (Good)
2 Revelry. Everyone should party like one big family, come on! (Neutral)
3 Hospitality. I want everyone to feel welcome under my roof. (Good)
4 A Local Smile. If I can make even one person's day better, I'm good all the way. (Good)
5 Helping Hand. A lot of people need help and I want to be the one to give! (Good)
6 Chaotic Happy. No matter how I have to do it, I'll make people smile... (Chaotic)
d6 Bond
1 Anyone can be friends with anyone!
2 I will go anywhere there are frowns to turn them upside down!
3 I like to treat everyone the same, with a sunny disposition!
4 Everyone wants to be happy in some way, and there has to be a way for all of us to be happy...
5 I have a big family of friends I've made over the course of my travels!
6 Part of being a great Lollipop guildie is fitting in!
d6 Flaw
1 My cheek muscles hurt sometimes from smiling so much...
2 I am told I'm too annoying about my cheeriness. But how can that be?!
3 I am too open and trusting.
4 I never take "no" for an answer.
5 Trying to make everyone happy, I sometimes make them unhappy.
6 People say I talk too much, but all I want is to make them happy! Don't they know that happiness comes from being with other people and talking, laughing, and sharing? What's the fun in being alone, all quiet and dour? You see happy people surrounded by warmth and love, not cold and dark, right? Right, so that's why I...


The Lollipop Guild is known far and wide across the realms of fantasy! People know them to be upholders of peace and happiness. Villains regard them as a nuisance.

Lollipop Contacts[edit]

Contact Description
Gerlitch Jackson One of the three heads of the Lollipop Guild, located in Munchkin Country, Gerlitch is a jolly and friendly face who welcomes newcomers with a smile, ever eager to recruit. He wears red and brown plaid.
Maorien Jeremiah Second of the three heads of the Lollipop Guild, Maorien is a spunky spirit full of gumption. He wears the green and lime colored plaid.
"Hairy" Earl Esry The third of the Lollipop Guild masters, Earl is the tough-acting one of the leadership. While he likes to be tough, it's the sort of tough from tough love that one appreciates. He wears solid blue colors.
Argol Otte Argol aspires to be as popular as the famous munchkin traveler, Ojo. He is sequestered as the main guild's janitor boy at the moment.
Pippy The runt of a family of five, Pippy recently got the prestigious position to be the guild ambassador to the nation of Quadling Country. He's a fairly precocious youth who is often unaware of his own shortcomings. The three guild masters often send other members after him to help clean up any mess he gets into.
Unko Runkle An old storyteller, Unko is a retired adventurer of the Lollipop Guild. He spends his days near the back of the guild, telling his tall tales about his adventures all over the land of Oz and trying to inspire new recruits to follow in his footsteps.

Non-Lollipop Contacts[edit]

Contact Description
Melfbyn Buttonlip A quadling in the nearby neighboring country, Melfbyn is a homely farmer that deals in produce with the guild. Every now and then, the guild helps him out with pest problems that threaten his crop yields.
Toot Also known as "The Wayfarer," Toot is a gillikin from the northern country. He is a cousin of Woot the Wanderer and seeks Princess Ozma's affections.
"Hairy" Earl Esry The third of the Lollipop Guild masters, Earl is the tough-acting one of the leadership. While he likes to be tough, it's the sort of tough from tough love that one appreciates. He wears solid blue colors.
Kuli Mary Kuli lives at the northeastern city-state of Keretaria. Seeing the state of the city-state under the control of the witch Wunchie, she solicits help from the Lollipop Guild to help overthrow the prophecy regarding Nox the royal Ox.
Orgmo A winkie in the eastern nation of Winkie Country, Orgmo is a talented tinsmith. Despite the malicious oppression from the Wicked Witch of the West and her army of monkeys, Orgmo still desires for all of Oz to enjoy his creations. As such, he has the guild help him with smuggled shipments.
Tuschi Tuschi is the royal mediator in the Oz castle for the guild. He acts as the monarch's direct line with the Lollipop Guild.

How Do I Fit In?[edit]

The Lollipop Guild is a fairly easy place for one to find their footing. Just be happy and, most importantly, make others smile too! They are not limited only to munchkins, while they are situated within Munchkin Country.

Lollipop Party[edit]

Because of the relative danger level in Oz, it is not uncommon for people to travel alone. The Lollipop Guild usually spares groups of three for jobs that are considered particularly dangerous. Otherwise, they typically fund solo wanderers.

Rank and Renown[edit]

The Lollipop Guild is not super organized or stratified. There are simply the three guild masters at the top command, and everyone else under them. While the guild does have reaches abroad, they are all lumped together with domestic members as one large rank below the guild master. This is a very free system that sometimes creates organic leaderships within groups.

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