Lollipop is an anthropomorphic pepper mint (it being mostly his head) with a body attached. He wears a steel blue job outfit, along with a sailor's cap.
Lollipop is a "Self Insert" of Emil "ace" Macko, but one of Mary's Forgotten Memories in the storyline of the game. He is first mentioned by Monster Vinnie In the Night 6's Ending Cutscene. In the deepscape, each of Mary's forgotten toy memories give the player hints on how to find him in each of the minigame. The player must find their words carefully to get the secret minigames, where the player must beat Lollipop to get a piece of the 4th star, which is white with red stripes.
How to find him
To find him, you got to talk to your toys, and when they say "If you have something to say, Say it now.", Type with your keyboard WHEREISHE. They will tell you how to find Lollipop and play one of his games to collect a piece of the 4th star.
- Candy's Adventure: After asking the Toy Car Where is he in Night 1, he tells you that you have to get 100 Coins in the arcade game "Candy's Adventure", then get back to the entrance of the cave, and jump to the top of it, like it's shown in this video , after that, you'll get to where Lollipop is, and after his continuous slowing laughter, you will be sent to a minigame where you, with the help of the Toy Car as your kart, will race lollipop in a race, you must take shortcuts to be able to beat lollipop in the race, ending with his laughter. This gives you the first fragment of the 4th star.
- Fishing with Candy: After asking the unicorn where is he in Night 2, it tells you that you must catch the fish in "Fishing with Candy" in the order: RED RED RED RED GREEN BLUE BLUE WHITE RED WHITE BLUE. You'll be sent to another one of Lollipop's games, where the unicorn is running towards him, and the player must jump over the obstacles Lollipop leaves behind him. After that, he will stop running, and the screen will cut to black. This gives you the second fragment of the 4th star.
- Cindy's Garden After asking the toy duck where is he in Night 3, it tells you that you must hit the holes in "Cindy's Garden" in order from the left: 2, 2, 2, 2, 2, 4, 1, 2, 4, 2, 3, 3, 1, 3. You'll be sent to a game similar to Frogger, crossing obstacles such as cars, trains, and logs. Once the player reaches him, the minigame will end, and the third fragment of the 4th star is given.
- Final Night After asking the toy robot where is he in Night 4, it tells you that you must re-confront the final problem. The player must beat the Final Night again. After the cutscene that follows, the screen will cut to black, and Lollipop speaks again. This time, he tells the player that he knows the toys told them, and now that he/she is there, they will play. You'll be sent to a Space Invaders-like game, moving left and right and attacking the ships, dodging their hits. Once all the ships are cleared, the screen cuts to black and the fourth fragment of the 4th star is given.
- Thank You Image After asking the teapot where is he in Night 5, it tells you that you must find him in the Thank You Image in the Extras Menu. He can be barely made out in between Withered New Cindy and New Candy on the left. When the player clicks on him, he will be sent to a game where Lollipop is running back and forth, and the player must catch the drops into the teapot. After enough drops have been collected, he will stop, and the game will return to the main menu. The entire 4th star is visible now, and the player must click on it to achieve the Ultimate Ending.
After the 6th night cutscene, having not found Lollipop
It was just another game
Another game like the ones we always played
You were supposed to find me
But then you never did
WHERE IS HE?
Like all the others in the box
I have become forgotten
Me, your favorite, and your best friend in the world
Where is he?
The game never finished
I'm still hiding,
waiting for you to find me,
find the pieces, and find me.
w h e r e i s h e ?
Just keep asking
Maybe ask the others?
After pressing the final star
You made it
You must be remembering a lot by now
I have one last thing for you though
One last thing for you to remember.
I'm tough, I can last for long, I can be sweet, I can be sour, and I stick till the end.
What is my name?
After entering Lollipop
You finally remembered, huh?
You finally found me
It was getting pretty boring, to be honest
Just hiding forever
At least we got to play games again
Did you enjoy them?
Of course you did
This was really fun
It was just like the old times
We should play my games again someday
Anyway, this is it
There's probably no more to do
You've reached the end
The ultimate ending
I don't have anymore games right now
But don't be sad...
These games won't be my last
Something is already in the works
There's a piece of it in that box, in the corner
If you'd like to take a peek at it...
After pressing the Final Star once everything is unlocked
I guess you must've grown bored?
I think I'm bored too...
Unless... You want to play some games again?
- If you press escape during one of his games, he will jumpscare you, along with a deep demonic laugh before the game exits.
- He also introduced one of Emil Macko's future games.
- If you press ESCape before selecting a game on his screen, having clicked on the 4th star once everything has been beat, the game will stay open, and a childish laugh will play.
- Lollipop could represent the creator of the Five Nights at Candy's games, Emil "Ace" Macko due to his quotes such as, "We should play my games again someday." And, "These games won't be my last. In fact... Something is already in the works."