Alvin and the Chipmunks and the Bond of Friendship

by CrashGuy41

Rating: everyone
Tags: Equestria Girls, Sunset Shimmer, Main 7 (EqG), Slice of Life, Crossover, Rarity (EqG), Original Character, Alternate Universe, Comedy, Romance
Length: 4387

The Chipmunks and the Chipettes are starting high school.

The Chipmunks and the Chipettes are transferring to a new high school in New York. There, they meet some new friends and reunite with an old one. Things are not well at their new school, however, as the local mean girl, Sunset Shimmer, is determined to make their lives a misery.

Can the youngest Chipette, Eleanor, get through her thick skull, and can the fashion diva, Rarity, convince Brittany to think of someone other than herself for once?

Published 2024-07-13 23:50:01 UTC
Last updated 2024-07-22 02:43:19 UTC

First Year in High School

It was a bright, sunny day at a high school in New York City. A young freshman girl with long, brown hair, fair peach skin and bright green eyes was putting up posters. She was wearing a light blue t-shirt, khaki-colored shorts, white socks, and red sneakers Her name was Chelsea Lee. She was the friendliest, most athletic and most popular girl in the entirety of Midtown High.

"Hey, Chels! Heads up!" a voice called out from behind her.

Chelsea immediately turned around and caught a soccer ball in both of her hands. The perpetrator was none other than the sporty, Rainbow-haired Junior tomboy, Rainbow Miriam Dash, one of Chelsea's friends. Rainbow might be the young captain of a lot of Varsity girls' teams, but she was a novice player compared to 14-year-old Chelsea. In other words, Chelsea was a sports prodigy, even gaining a nickname on the halfpipe, known as the Princess of the Pipes. She even earned one of the best spots on the JV basketball team for the Midtown Cowboys, which was Midtown High's team name.

“Seriously, Rainbow? If I didn’t know you any better, I’d think that you’re just asking to get into detention,” Chelsea smirked.

She tossed the ball back to Rainbow, who caught it easily.

"At least it's better than what you're doing."

Chelsea just rolled her eyes and smiled at her upperclassman. She knew that all Rainbow Dash wanted was to be active all of the time, which often resulted in her getting into trouble.

"Well, at least I'm not going around the school kicking a soccer ball everywhere I go."

Chelsea then grabbed her backpack and started walking down the hall towards her locker. Unbeknownst to her, however, she was being watched by a pair of mean-looking eyes. Burning, hate-filled eyes. Chelsea then came to her locker and opened it. Parting back her hair in the mirror, she then grabbed two books out of her locker. Looking back into the mirror, she received quite a shock at what she saw. It was a girl with fiery red and yellow hair glaring at her with those mean-looking eyes. She quickly spun around to face the girl.

"S-S-S-S-S-Sunset! H-H-H-H-H-H-H-H-How long have you been standing behind me?"

"Two minutes. Care to explain why you're putting up those posters about the Fall Formal Princess?" Sunset snarled.

"It's because the principal told me to. You know how he is about these things. He wanted to advertise the event to the school in case any incoming Freshmen would be interested."

"Who in their right mind would even think about going up against me?! Once they hear about how things work around here, they're sure to turn tail and back out from the competition!"

Unbeknownst to them, they were being watched by someone whose voice Chelsea immediately recognized.

"Hey, you! Back off!" the voice said.

Sunset turned her head and saw what looked like a chipmunk with blue eyes, a red sweatshirt with a big yellow letter A on it, red baseball cap, and blue shoes.

"What did you say?"

"You heard me! I said... BACK! OFF!"

The two face each other in the hallway with angry faces. Almost immediately, Sunset smirked right in his face and yanked his hat down over his head.

"You must be new here, Freshman."

The chipmunk lifted his hat back up and glared at her.

"I can do things around here however I please and you can consider yourself lucky for this one moment. But know this, next time, I won't be as nice."

And with that, Sunset walked away down the hallway.

"I don't believe it. I-I-I-I-I-I-I-I-It can't be!" Chelsea gasped. "Alvin?!"

Alvin turned around and immediately noticed that Chelsea was talking to him. He recognized her right away and gave her a big hug.

"Oh, my gosh! How many years has it been since we've seen each other?" he asked.

"It's been at least three years, Seville. How are the others doing?"

"We just got enrolled into the school today."

"No kidding? Well, let me be the first to welcome you, your brothers and the Chipettes to Midtown High!"

"Thanks. But, you're a Freshman too, aren't you?"

"Well, yeah. But I pretty much know the layout of the school like the back of my hand. Are you lost?"

"Kind of. I'm looking for the gymnasium. Dave's going to set up our equipment there eventually for the upcoming Fall Formal. We're the entertainment."

"That's wonderful news, Alvin! I can't wait to hear you guys perform again! The gym is just through those two double doors over there."

Chelsea pointed to a set a double doors behind her, which led to the gym. Alvin then started to head off in that general direction.

"Thanks, Chels! I'll tell the others I saw you!"

"You do that! And tell Brittany about the upcoming Fall Formal Princess sign-ups! You and I both know how competitive she is with those things!"

"Will do, Chelsea! And thanks again!"

"You're welcome, Alvin! And take care!"

As he disappeared through the double doors, Chelsea chuckled to herself.

"Some things just never change with that boy."

Later that day, Alvin was setting things up in the gymnasium with his two younger brothers, Simon and Theodore and their female counterparts, the Chipettes.

There was Simon, Alvin's younger brother. He was a male chipmunk that had blue eyes and wore round, black glasses, a blue shirt and red shoes.

The youngest of the Chipmunks was Theodore. Theodore loved to eat. He had green eyes and was wearing a green shirt with orange shoes.

The eldest Chipette was Brittany. She was Alvin's girlfriend. She had dark blue eyes and auburn-colored hair tied in a ponytail. She wore a pink dress, a yellow scarf, purple leggings with yellow leg warmers, and pink shoes. She was very fashionable, if not extremely selfish at times.

Jeanette was Simon's female counterpart and girlfriend. She had dark green eyes and dark brown hair, also tied in a ponytail. She was wearing round, black glasses, a dark blue shirt, a purple skirt, a purple hair tie, white leg warmers, and blue shoes.

Finally, there was Eleanor. She was the youngest, and ironically, the most mature of the Chipettes, as well as Theodore's girlfriend. She had brown eyes and blonde hair that was tied into two pigtails. She wore a white shirt underneath a green vest, along with a striped green tie and a green skirt. She also had on a pair of white knee-high socks and black shoes.

"I honestly hope everything goes well," Jeanette said.

Just then, she ended up tripping on her own shoe and nearly lost her balance. Thankfully, Simon caught her just in time.

"Thanks, Simon."

"Don't mention it," Simon replied with a smile.

"Try to be more careful next time, Jeanette," Brittany groaned as she rolled her eyes.

Jeanette glared at her sister. For five to six years, she had endured her sister's constant verbal abuse due to her being the clumsy one. She was about ready to tell her off, when from out of nowhere, they all heard a voice nearby.

"INCOMING!" the voice shouted.

That's when a bunch of streamers started heading down in their general direction.

"DUCK!" Alvin cried.

The six of them did just that as the streamers came tumbling down. Brittany soon emerged from the multi-colored streamers and got them off of her.

"Why don't you watch where you're throwing these things?" she snarled.

Eleanor jabbed her in the stomach with her elbow in frustration.

"Brittany! That's the person in charge of the event planning!" Eleanor hissed.

Standing right in front of them was a girl that was the same age as Rainbow Dash, but instead of long, rainbow-colored hair, she had pink poofy hair that emphasized her energetic personality.

"Sorry. Sometimes I get a little carried away with party stuff. Anyways, my name's Pinkie Pie. Nice to meet you!" Pinkie said excitedly, while shaking Brittany's hand.

"Uh... okay," Brittany said nervously.

"Are you by any chance the famous Chipmunks and Chipettes singing groups?"

"As a matter of fact, we are," Alvin said smugly.

"Alvin!" Simon hissed, elbowing him in the stomach.

"Thought so. So, what are you doing here?" Pinkie inquired.

"Well, for one, we're the new students here. But we're also here as the entertainment for the Fall Formal," Alvin said.

"Not to mention I want to sign up for Fall Formal Princess and show everyone that I'm the one that they should vote for for my natural beauty," Brittany said as she patted her ponytail.

"Is that so?" Pinkie asked.

She then reached into her hair and grabbed a clipboard, along with a pen for Brittany to sign.

"Well, you just need to fill out this form and you'll be our third entry for the coveted Princess of the Fall Formal crown."

Hearing those words made Brittany's jaw drop.

"Third entry? Let me see that!"

She grabbed the clipboard and pen, then read the two entries from before. The entries read Sunset Shimmer and Missy Snootson. The latter of whom made Brittany furious. She did not like Missy one little bit ever since their days in Elementary school.

"I'll show that Missy Snootson that I'm the one who deserves the crown! Not her!"

She immediately signed her name and gave it back to Pinkie. The entry read Brittany Miller, even though she and her sisters were technically living with the Chipmunks. That aside, Pinkie was more than happy to see that someone else was going up against Sunset Shimmer for Princess of the Fall Formal.

Just then, the doors opened and a girl wearing about Pinkie's age with blonde hair tied in a short, puffy ponytail at the bottom walked in with a crate of fizzy apple cider. She wore a brown Stetson hat and talked with a southern drawl, despite the fact that she lived in town. The girl's name was Applejack. She was a local farm girl that helped out at her family's farm, Sweet Apple Acres, known for their A-Quality apples and apple cider.

She set down the crate she was carrying on a table, then wiped the sweat from her forehead due to how heavy it was.

"Hey, aren't you the new kids Chelsea's been going on about?" Applejack asked.

"Uh... yes?" Jeanette answered sheepishly.

"Thought so. And that cap-wearing fella really gave Sunset Shimmer the what-for today."

Applejack then took a bottle of apple cider and removed the metal cap with her teeth. She then spat it on to the floor and started drinking it, since she was thirsty from carrying the heavy crate in earlier.

"Little Brittany Miller here is going to run against both Missy Snootson and Sunset Shimmer for Princess of the Fall Formal," Pinkie explained.

Shocked at hearing this revelation, Applejack spat out her sip of her family's famous apple cider.

"Another Freshman going up against Sunset Shimmer, Pinkie? Seriously? What is Principal Harrison thinking? You and I both know that once Sunset Shimmer finds out about this, that she'll show no mercy with the backstabbing!"

As if on cue, the gymnasium doors flung open and standing right in plain sight, was none other than Sunset Shimmer herself.

"THIS! LOOKS! TERRIBLE!" she bellowed as she stormed in.

Terrified of her presence alone, Theodore immediately hid behind Eleanor as he trembled in fear.

"And I suppose THAT'S Sunset Shimmer?" Brittany asked, unimpressed.

"Yep," Alvin replied.

"There should be more streamers near the stage and fewer balloons!" Sunset fumed, popping some of the balloons with her nails.

She then inspected the stage and was not impressed by the banner that the Chipmunks and the Chipettes had set up.

"Are you kidding me?! What is this? The banner looks like it was made with crayon marks!"

"It was not! Dave made it!"

"Oh, yeah? Then why do the letters look like they were written by a bunch of five-year-olds?"

"Maybe because little Brittany here helped with the preparations," a voice laughed from behind her.

Brittany immediately recognized the voice as one Missy Snootson. Missy was a girl the same age as Brittany. She had brown, curly hair that had a light blue bow on top. She wore a blue-and-white dress, long white socks, and black shoes.

"As if things couldn't get any worse, here comes Missy Snootson," Brittany grumbled.

"Well, well, looks like you and your boyfriend stood up to one of the meanest girls in the school. Gotta say, I never expected someone like you to stand up to someone like her."

"Shut! UP! Snootson!"

"Why? So you can tell me how unqualified you are to compete for Princess of the Fall Formal? HA! Yeah, I don't think so, Miller."

"WAIT, WHAT?!" Sunset exclaimed. "You two lowly Freshmen are competing against me?!"

"You got a problem with that, bacon hair?" Brittany snarled.

"No. In fact, this just makes things even more interesting."

Sunset slowly walked over to Brittany with an evil smile on her face.

"Now that I know who I'm running against, all I can say is... Be prepared to lose."

"My thoughts exactly."

And with that, Sunset slowly walked out of the gymnasium. Applejack took off her hat and wiped her forehead nervously.

"Whew. That was pretty intense," she said.

"I hope Brittany knows what she's doing," Alvin said.

"My thoughts exactly, Alvin," Simon agreed.

Later that evening, the Chipmunks and the Chipettes arrived home at their white-and-red two-story house, which owned by their caretaker, Dave Seville. Dave had black hair, wore a red shirt underneath a pink sweater, light brown pants, and dark brown shoes.

"Hey, kids, how was your first day of school?" he asked.

"It was... eventful," Simon said, struggling to find the right words.

"Eventful, how?"

"Brittany signed up for Princess of the Fall Formal," Alvin said, chiming in.

"Princess of the Fall Formal? That's the big event that determines who gets to ride the float in the parade, isn't it?"

"Uh-huh."

"I can see why she would want to do it. No one knows how to please crowds better than the two of you, Alvin."

"Ah yes, Mr. Crowd pleaser himself. Hold your applause, please."

"Alvin. Don't start."

As the conversation was going on, Brittany made her way up to the bedroom and looked out the window in curiosity.

"Princess of the Fall Formal. That would finally get me all the respect I ever wanted," she said.

Just then, out nowhere, Dave suddenly lost his patience and yelled Alvin's name.

"ALVINNN!!!" he shouted.

Brittany facepalmed and sighed in annoyance.

"Not again," she grumbled.

Despite all of the odds that were about to be against her, Brittany knew that this was going to be one competition that she would never forget.

Author's Note

For those who don't know, Chelsea's look is inspired by the Marvel Adventures Power Pack character, Chrissy Fletcher, from the Fantastic Four/Power Pack four-part crossover miniseries from the mid-2000's. Also, the team name, Midtown Cowboys, is a reference to the Telltale game, Sam & Max Save the World Episode 2: Situation Comedy. There is a sitcom in that Telltale episode with that name with a goal that you need to complete in order to progress to the next part of the story.

Also, when the characters eventually sing, here's the color code for the characters.

Pinkie Pie

Applejack

Rarity

Rainbow Dash

Fluttershy

Sunset Shimmer

Brittany

Simon

Jeanette

Alvin

Eleanor

Theodore

You may have noticed that Twilight isn't on the list. That's because I won't be introducing her for this particular series until this story's sequel. More on that when it actually gets published.

Meet Fluttershy

The next morning at school, Jeanette was walking in the hallway when she suddenly ended up bumping into a girl with long, pink hair, light purple eyeshadow and even had a butterfly hairpin on the left side of her hair. The girl's name was Fluttershy and like Pinkie, Sunset, Rainbow, and Applejack, she was also a Junior. By bumping into her, she managed to knock the flyers clean out of her hands.

"Oh, my gosh! I'm sorry!" Jeanette apologized as she started picking the flyers up off the floor. "I am just so clumsy."

"No, no. It was my fault. I wasn't watching where I was going," Fluttershy said.

As she was picking up the flyers, Jeanette decided to look at one of them and see what it was that Fluttershy was advertising. It turns out that they were flyers for a local animal shelter.

"You work at the Queens Animal Shelter?"

"Um, I volunteer, actually."

Jeanette then handed her the remaining flyers as the two of them stood up.

"Thanks for helping me."

"You're welcome. My name's Jeanette, by the way. What's yours?"

"It's Fluttershy," Fluttershy squeaked.

"Fluttershy? That's kind of a strange name, but a pretty one, nonetheless."

"Y-Y-Y-Y-Y-Y-Y-You really think so?"

"Sure. In fact, I think it's very, um... unique."

Before the conversation could go any further, the school bell rang.

"So, uh, do you think you could show me what you do at the animal shelter after school today?"

Fluttershy nodded in response to Jeanette's question.

"Great! I've always wanted to go there."

Later that day, Chelsea was outside on the soccer field with Rainbow Dash getting some practice goals in the soccer nets. Today, however, something was really bugging her, as she was kicking the balls with full force. While normally calm, Chelsea is sometimes known to have quite a short fuse on her.

"Stupid Sunset!" she grumbled as she kicked one of the balls. "Trying to tell me what do with the stupid Fall Formal! UNH!"

She then kicked another ball at full force, as well.

"Woah, woah. Take it easy, champ. You're going to rip the goal net," Rainbow warned.

"Shut up, Dashie! I'm not in the mood for a pep talk, right now!"

Angry, she kicked a third ball in the net at full force. Rainbow Dash knew that something had to be done before Chelsea ended up ripping the soccer net.

"Look, I know you're upset at Sunset Shimmer, we all are. But taking your anger out on the net isn't going to solve anything."

"You're one to talk! The last time I saw you blow a fuse, you were practically doing the same thing!"

"I had to practice, anyways! Don't be drawing comparisons to the time I thought Applejack broke her promise to me!"

"AARGH! You are so immature! You know what your problem is Rainbow Dash? You can be extremely egotistical and self-centered at times!"

"BUT AT LEAST I HAVE ENOUGH DECENCY TO CARE ABOUT MY TEAMMATES ON THE FIELD!"

"THAT'S BESIDE THE POINT, DASH! YOUR ARROGANCE DURING THAT ONE GAME NEARLY COST US THE ENTIRE MATCH! IF IT WASN'T FOR COACH PUTTING ME IN, I GUARANTEE YOU THAT WE WOULD'VE LOST!"

"GRRR! WHY DO YOU HAVE TO BE SO STUBBORN?!"

"BECAUSE I HAVE TO DEAL WITH SUNSET'S TRASH TALK MORE THAN ANYONE ELSE IN THE ENTIRE SCHOOL, OKAY?!"

Rainbow gasped. She had no idea that Chelsea was undergoing so much stress because of Sunset.

"Don't you get it, Riley? Ever since I first started here, Sunset's been giving me grief every single chance she gets. Wouldn't you feel the same way if it was you instead of me?"

Rainbow didn't know what to say. She had never seen Chelsea get this emotional before.

"Chels, look..."

"Forget it, Dash! I'm tired of you trying to cheer me up by saying you know how I feel! Because you don't! You don't even know the first thing about me!"

And with that, Chelsea stormed off and headed back inside, as it was beginning to look like rain. Thunder was heard in the distance as Rainbow looked up. She saw storm clouds directly above her and was soon caught in the rain. She ran back inside as quickly as she could to dry her hair off.

Sometime later, during lunch, Eleanor had noticed that Chelsea wasn't sitting with them like she did the other day. Instead, their friend was sitting all by herself looking very angry. She even had her arms folded to emphasize how angry she was.

"Uh, hey guys? Is it just me or is Chelsea acting a bit strange?" Eleanor asked.

"Strange as in, how?" Simon inquired.

"Well, I mean, yesterday she was all upbeat and happy to see us. And yet, today, she seems to be extremely angry about something."

"I think I know what's wrong," Jeanette chimed in. "Sunset Shimmer."

"Oh, puh-lease, Jeanette! How would you know what was bothering Chelsea?" Brittany snarked.

"Because I talked to her just before she went out on the field to practice for the upcoming game. Really, Brittany. Don't you think you're being a little bit insensitive?"

Brittany glanced over at Chelsea, who was now eating her lunch while still angry at Sunset Shimmer.

"What has this world come to?" she asked herself.

After school that day, Fluttershy showed Jeanette around the Queens animal shelter that she volunteers at.

"Wow, Fluttershy! This is amazing!" Jeanette beamed.

"Thanks," Fluttershy giggled.

As soon as Fluttershy put down her backpack, a wooden tambourine rolled out and landed on the floor. Jeanette picked it up and was intrigued by it.

"You play the tambourine?" she asked.

Fluttershy took the instrument from her and slipped it back into her bag.

"I-I-I-I-I-I-It's just a little hobby of mine. Rainbow Dash keeps going on about wanting to form a band, but I'm a little nervous when it comes to singing."

"Fluttershy, how do you think I feel when I'm up there on stage with my sisters and the boys? I have to wear that heavy keytar around my neck during our live stage performances and I'm always afraid I'll mess up when it's time to sing."

"B-B-But... B-B-B-B-B-But..."

"Fluttershy, look. I know it's hard. But just give it some thought."

Jeanette started walking towards the doors to leave and was soon stopped by Fluttershy.

"W-W-W-W-W-Where are you going?"

"I need to run a few errands for Dave. Because we all know that Alvin's not going to do them. I'll be back in about twenty minutes, tops."

She got on a bright, blue bicycle and pedaled off as the rain started to clear up. As soon as she was out of sight, Fluttershy let out a deep sigh and looked at the animals in shelter. One animal that she was fond of was her spoiled, white pet rabbit, Angel.

"Be in a band? Maybe she's right. Maybe I can do it. You know, there's just so much more that people don't know about me."

She grabbed the broom and started cleaning the floor as she spoke to Angel.

"Do you think the coast is clear?
No one to see, no one to hear?
Me sing out my song.
I think we're all alone.

I don't need my name in lights.
That's not where I've set my sights.
No-oh-oh-no. Not me.
I don't need a stage to SING!"

She then put the broom away and started dancing while playing her tambourine.

"I like the quiet.
I like the calm.
To turn it up...
To sing along!

I'm not just shy.
Look close and you will see...
There's so much more to me."

After playing her tambourine for a bit, she put it back in her bag and took out her hairbrush. After doing so, she then started brushing Angel's fur at the washing station.

"I'm just fine rehearsing on my own.
My hairbrush is my microphone.
Look out, now! I'm in the zone! Yeah!
Can you feel it?

I like the quiet.
I like the calm.
To turn it up...
To sing along!

I'm not just shy.
Look close and you will see...
There's so much more to me."

She then heard her phone go off in her backpack and immediately rushed towards it. Answering it, she saw that it was her friend, Rainbow Dash. It was a text that read, I really want you to be in this band, Flutters. You're the best tambourine player ever!

"I speak soft out in a crowd.
I whisper Am I being too loud?
But when I close that door...
The crowd, it just wants MORE AND MORE AND MORE!"

She answered the text almost immediately after giving it some thought. Her response read, I'll do it! The new girl, Jeanette, convinced me to.

"I like the quiet.
I like the calm. (oh-oh-woah-oh-woah)
To turn it up...
To sing along!

I'm not just shy.
Look close and you will see...
There's so much more to me."

She then started dancing like a ballerina after answering the text, showing just how good she felt about accepting the offer.

"I like my friends.
I like my pets. (oh-oh-woah-oh-woah)
I like to rock...
Do pirouettes. (oh-oh-oh)

I'm more than shy.
I'm more than you can see.
There's so much more to me."

Just then, the door opened and Jeanette walked in.

"Hey, Fluttershy! I'm back! Sorry I took so long. The traffic was murder," Jeanette said. "So, have you thought about it?"

"Uh-huh. And I just responded to Rainbow Dash's text. And I said YES to being in her band!" Fluttershy squealed.

"Th-Th-Th-Th-Th-Th-Th-Th-That's amazing, Fluttershy! Wait'll Chelsea hears about this! That's sure to cheer her up, for sure!"

"Well, I certainly hope so. She was acting real huffy at school, today."

"You can blame Sunset Shimmer for that," Jeanette sighed. "But, in any case, why don't I text Chelsea and tell her the good news? Oh, she'll be so happy! I just know it!"

Jeanette got out her phone and started texting Chelsea about Fluttershy's decision to join Rainbow's band. Despite her good intentions, little did she know that this harmless text was about make things a lot more complicated with Sunset Shimmer.

Author's Note

Yes, Rainbow's real name is Riley. When I looked it up, the definition of the name means courageous. That perfectly suits Rainbow Dash. Also, Fluttershy's real name is Fawn, a reference to the fact that she loves animals and that her favorite animal in the story is the deer.