Read stories! We've got a bunch of the best fanfics to dive into starring Cheerilee and the other underappreciated pones.
Go get them below! Thanks to Whisper Key for the scouting.
Slice of Life
The Teacher and the Hippogriff by Nyronus
https://www.fimfiction.net/
Cheerilee has, by and large, been detached from the events at the School of Friendship. She heard the rumors about a total meltdown at the school, and even worse ones about a diplomatic incident that followed, but by and large, she's simply wished Twilight well and went about her business of helping all the young ponies of Ponyville grow.
Then, one day, not too long after the School of Friendship reopened, a new young mind flies into her life.
"Teach Me Goodness" by Posh
https://www.fimfiction.net/
On the last day of school before summer vacation, Cheerilee informs her students that she's going to pursue her doctorate in Fillydelphia, and won't be returning as their teacher in the fall. Her friends and students alike spend her last night in Ponyville bidding farewell and showing their appreciation for her, each in their own unique way.
But one student, in particular, has a hard time coping.
Wassail, Wassail! by Skywriter
https://www.fimfiction.net/
A holiday tale in which Cheerilee learns the true meaning of the word "wassail"; Granny Smith fails to learn the true meaning of the word "polymath"; and somehow, amidst it all, three flowers finally begin to put down roots. Happy Twelfth Night, everypony.
Flashes on the Horizon by Goblin Scribe
https://www.fimfiction.net/
Something's happening. Cheerilee isn't sure what. All she knows is what she saw, and that's not much to go on—no more than a glint of flame on the dark horizon. Whatever it is, it's very far away.
The moon is high in the sky, but she doesn't plan on sleeping tonight. Instead, she will take her telescope, sit by the lake, and wait. Perhaps she will see more.
School Daze by Paleo Prints
https://www.fimfiction.net/
After her students release the spirit of Discord on an official field trip, Cheerilee finds herself out of a job. With no opportunities in Ponyville, the schoolmare takes a job offer in the inner city area of Canterlot's old mining town. Can even she overcome the insanities of her colleagues and apathy of her students in time to pass her next annual review? And who is the mysterious backwards-talking filly following Cheerilee around? Luna's School for Disadvantaged Youngsters will never be the same!
Crimps and Prance by Conner Cogwork
https://www.fimfiction.net/
Cheerilee is becoming frazzled after a long semester. But when a friend recommends a new dance club in Ponyville, she feels she's too old to partake in today's current hip scene... or is she?
Breaking The Sound Barrier by SusieBeeca
https://www.fimfiction.net/
Young Cheerilee is happy to have finally settled down with her family in a nice town like Ponyville, and she's not about to let her nervousness about her first day of school stop her from making new friends. Most of her classmates seem nice, but...
There's one young colt who'll barely say two words to her. And she's determined to find out why.
A Town that Time Forgot by Freglz
https://www.fimfiction.net/
One night, on Hearth's Warming, Diamond Tiara returned to her hometown of Ponyville.
She'd hoped that some things might have changed.
She didn't expect somepony to change so much.
When Space Met Time by Impossible Numbers
https://www.fimfiction.net/
Twinkleshine had barely started kindergarten when she first met the universe. Like most first meetings, it had been awkward, not under the best of circumstances, and a single instant that ignited a lifelong passion, which would inevitably end with late nights and concerned parents.
Just a Regular Day for the Bug Resistance by Tennis Match Fan
https://www.fimfiction.net/
Queen Chrysalis is trying to take over Equestria!
Meanwhile, Berry Punch sleeps in. She's a member of an elite guard, and she sleeps in?! Pinkie doesn't mind, but Bon Bon does. Being an Elite means watching out for Changelings. Is Berry good at what she does?
The Perfect Drink by GaPJaxie
https://www.fimfiction.net/
Every year, on Hearthswarming, Berry Punch makes a drink for Fluttershy. One perfect drink.
Keepers by Bad Horse
https://www.fimfiction.net/
Berry Punch made a mistake, and now she has a problem. A little problem that could grow into a big problem. Question is, her artist friend Happy says, is it the kind of mistake that needs fixing? Or the kind where fixing it would be another mistake?
Apple Knots by BlazzingInferno
https://www.fimfiction.net/
Lotus is a professional masseuse. She sees the pony below the skin, and tends to coax just as much out of their mouths as their muscles. Late one day, she gives three very different massages to three close friends, all of whom mention a name she isn't familiar with: Applejack.
Aloe and Lotus: A Slow Day by Dream Bolt
https://www.fimfiction.net/
Aloe and Lotus are having a slow day at the spa, and are rather bored. When Rarity shows up by herself, and finds nopony else to talk to during her beautification, she ends up striking up a conversation with the two ponies who own the spa.
Comedy
Cheerilee's Thousand by xjuggernaughtx
https://www.fimfiction.net/
"How could somepony as amazing as you not have a Special Somepony on Hearts and Hooves Day?"
With that single sentence, a thousand memories came flooding back to Cheerilee. A thousand memories of a thousand terrible dates...
The Good Ship Lifestyle by A Hoof-ful of Dust
https://www.fimfiction.net/
Why won't everypony leave Cheerilee alone about being single?!
Cheer On by GWFan
https://www.fimfiction.net/
After a budget cut, Cheerilee is replaced by a younger and stricter teacher. Cheerilee searches for a new job in Ponyville while her students deal with the new teacher. However, everything is not what it seems. Can Cheerilee use her vast knowledge to save her students and Ponyville?
Of Time and Cavities by RavensDagger
https://www.fimfiction.net/
My name is Minuette, but a privileged few know me as Agent Colgate, Dental Practitioner. We hide in the shadows, ever watching out for pony's teeth. When cavities strike, we are there. Saving Equestria, one toothache at a time.
The Other Dentist by Sorren
https://www.fimfiction.net/
For Colgate, it's just any other day, complete with scared foals, teeth, floss, gigantic caverns, plaque fiends, and an evil oral menace known as Dr. Cavity.
Just an average day.
Chompers by SpaceCommie
https://www.fimfiction.net/
Granny Smith insists that Applejack has to go to the dentist.
But she doesn't have to like it.
At all.
We Get Diplomatic Immunity, Right? by Pascoite
https://www.fimfiction.net/
Very few ponies have ever gotten a dressing-down in person from Princess Celestia. So at least Berry Punch has that going for her. Even though what she did wasn’t technically illegal.
Fluid Exchange Under Closed Timelike Curves by CoffeeMinion
https://www.fimfiction.net/
This might be the story of Berry Punch going home with a time traveler, or it might be the story of what happens after.
Time travel is confusing enough when you aren't rip-roaring drunk, y'know?
Berry Punch's House Can Talk by Glimglam
https://www.fimfiction.net/
Berry Punch likes to think that she's a fairly-normal pony, who lives in a fairly-normal town filled with other fairly-normal ponies.
Unfortunately, her house is anything but normal, in any sense of the word.
Wine And Toothpaste by Aragon
https://www.fimfiction.net/
Beer tastes bad, Whiskey is just horrible, and Colgate does not like drinking.
This is the story of how Colgate met Berry Punch for the first time, and how she saw a bartender who was clearly a ninja.
Special Treatment by CategoricalGrant
https://www.fimfiction.net/
Forced into an exhausting and frustrating job by Twilight during what should be a relaxing summer break, Spike is flabbergasted to find that his first pay check will be coming late. The spa's owners, however, are confident they can give him something to tide him over until then.
A Bird In The Dryer... by Estee
https://www.fimfiction.net/
Running a spa isn't easy. Lotus Blossom is expected to lower the stress levels of an entire town on demand, with nopony ever thinking about what those demands might be doing to her. Keeping the La-Ti-Da Spa functional, calming, and more or less in one piece means paying attention to the small details. Birds in the dryer vent counts as a small detail. But at least that's just a minor problem.
Or not.
Sad/Dark
Smiling Flowers by TheBrianJ
https://www.fimfiction.net/
A Cutie Mark is meant to represent the personality and special talent of each pony that has one. Cheerilee's flowers symbolize her desire to help her students bloom, and the smiles represent the cheer that she hopes to bring to their lives.
At least...that's what she tells everypony who asks.
A Night in Tartarus by SockPuppet
https://www.fimfiction.net/
Dr. Minuette will treat any patient. Even Cozy Glow. Even if dentists don't usually do Tartarus calls...
Set sometime between Seasons 8 and 9. Inspired by the old fan name for Minuette, "Colgate the Dentist."
It Spills Over by ambion
https://www.fimfiction.net/
When you fear the cure worse than the affliction, how can you ever hope to recover? For Berry Punch, there's never been an easy answer.
And when she is forced to confront consequences worse than any she could have imagined, it's just going to get harder.
With only her newfound desperation to drive her forwards, Berry Punch throws herself into what might truly be her last living attempt at recovery.
Shipping
The F-Grade Drinking Game by James_Corck
https://www.fimfiction.net/
Cheerilee and Twilight Sparkle get together for an exam correcting session. What sound like a boring plan for a Sunday night turns into something else when Cheerilee and Twilight play Cheerilee's favourite game: The F-Grade Drinking Game.
Aubade by TheJediMasterEd
https://www.fimfiction.net/
Miss Cheerilee has always looked out for her former pupil, Pinkamena Diane Pie ("Pinkie" to her friends).
Hooves must always (always) look after his current employer, Roland Bertram Aethelnoth Whickers the Third, Viscount Astley ("Bertie" to his friends).
But when Bertie met Pinkie, something happened that neither the schoolteacher nor the butler had looked for.
...But It Often Rhymes by Posh
https://www.fimfiction.net/
For four years, Sunset Shimmer has carried a torch for Miss Cheerilee, and for four years, she's struggled to look at her without thinking of the one who got away.
Teach Me Beauty, Teach Me Grace by PropMaster
https://www.fimfiction.net/
Rarity helps Cheerilee remember that she is an amazing mare.
A Stallion for the Time Being by Sharp Spark
https://www.fimfiction.net/
Minuette is determined to have a nice date with a nice stallion, no matter what that takes.
Twilight Sparkle just wants her to stop wreaking havoc on the time-space continuum.
Things get complicated.
Best Friends, Too by shortskirtsandexplosions
https://www.fimfiction.net/
Minuette and I have got to be the absolute best friends in all of Equestria. Or at least we thought so... before running into Lyra and Bon Bon.
Lágrimas del Corazón by Marcibel
https://www.fimfiction.net/
Sometimes a little tequila can make things a little clearer and a lot more complicated, be it about one's future or one's past.
And Berry really needs to stop drinking at work.
Berry Bitters and Apple Sours by King of Beggars
https://www.fimfiction.net/
For the first time in a long time, the Apple Family Reunion is being held somewhere other than Sweet Apple Acres. Big Mac decides this is his chance to finally have some time to himself and volunteers to stay behind to look after the homestead. But time alone doesn't mean that the chores can be ignored.
Berry Punch has had her eye on a certain stallion for a while now, and with his family out of the way, it's the perfect chance to test the waters.
Drama
A Former Student of Mine by Pascoite
https://www.fimfiction.net/
Sweetie Belle had never really considered how so many ponies contributed to the mosaic of her life. At least until she thought she might not get another chance for one of them.
Hindsight by Jack of a Few Trades
https://www.fimfiction.net/
Hearts and Hooves Day was a whirlwind, especially for Cheerilee and Big Macintosh. They remained friends in wake of the fiasco that almost ended in hasty marriage, and Cheerilee never gave their friendship any further thought. They were just friends, nothing more.
However, when she learns of Big Mac and Marble Pie's fling over the Hearth's Warming holiday, Cheerilee begins to dwell upon her friendship with Big Mac. Could there have been something more to their relationship that she hadn't realized before?
After all, hindsight is 20/20.
Teacher's Pet by Pascoite
https://www.fimfiction.net/
Fair or not, most classes have that one perfect student, that one little flower that the teacher can't help but adore. Cheerilee's class is no different.
Mrs. Robinson's Stand by WishyWish
https://www.fimfiction.net/
Four by hundreds of hooves, they march in dreary lockstep towards their cages, to serve their fate as beasts of burden. From all over the nation they came to this place in the name of friendship, but now their colors are struck and their ears drooped; scorching sulfur invading their nostrils as heavy chains bear them into capitulation.
Tempest Shadow, commander of the armies of the north and mistress of her own name, has subdued the capital of the largest nation in the known world without a single casualty on either side. She has bested three of the four legendary alicorns in combat, and chased away the last. Every obstacle in her way has been found wanting...save for one.
This is a story of the pillar that would not fall.
Veneer by Pascoite
https://www.fimfiction.net/
Aloe and Lotus love the looks on their customers' faces during a nice soak in the tub, a relaxing massage, a new pony greeting them in the mirror. But it wasn't always that way, and even now, the occasional difficult customer can prove trying.
Adventure
All the Time in the World by Adda le Blue
https://www.fimfiction.net/
Everypony knows that the future is predestined; the very existence of cutie marks proves it. Still, Minuette isn't so sure that she has to make the same mistakes twice.
Two ponies look to the future, and all the while one looks back to the present.
