One sunny day in the Inkwell Isles, Gwen attends her latest theater class with her fellow classmates. Gwen brings along her cup brothers along with her fiancé Clarence to her class at the Inkwell Community Theatre. Her teacher and theatre director Sally Stageplay has everyone seated for announcements.
"Well, this should be fun." Clarence said as he and Gwen sat down.
"Just you wait my love." Gwen said.
"Hopefully Sally will give us another chance." Mugman said.
"Guys, best behavior this time. And no sabotaging each other's auditions!" Gwen scolded the cups.
"We're sorry Gweny. We learned our lesson!" Cuphead protested.
"Oh, have you?" Gwen asked, reminding him of the last time he sabotaged the Devil and Mugman's auditions.
"Easy honey. Maybe they have learned their lesson." Clarence tried to calm Gwen down.
Just then, Sally made her grand entrance on the stage.
"Good morning students!" Sally greeted loudly.
"Good morning Mrs. Stageplay." All the students greeted.
"I hope you're all rested and ready for the big announcement!" Sally said.
"Ooh!" All the students said.
Unknown to Gwen and Clarence, the Devil and Henchman appear in the back row.
"Ah. Here we are back at the theatre. Hopefully there'll be a new play so I can get the lead role this time without those stupid cups interfering." The Devil said evilly.
"Now then everyone, as you all know, the Shakespearean Festival is coming up. And we have been asked to put on a play this year!" Sally announced.
Everybody gasped and cheered.
"Wow. Shakespeare huh?" Clarence asked.
"Yeah, every year we go to a fun festival in honor of William Shakespeare, you get to dress like we're in the Middle Ages, games, food, dancing and all that stuff." Gwen explained.
"Wow. I never been to one of those." Clarence said.
"You will now." Gwen said.
"Quiet!" Sally scolded.
Gwen and Clarence quickly turn their attention to Sally.
"Anyway, the play I decided that we're going to do before the festival is… Romeo and Juliet!" Sally announced.
Everybody gasped.
"Ooh. The tragic tale of lovers huh?" The Devil asked.
"Duh, that play made me cry because they both die in the end." Henchman said, wiping a tear.
"I've gathered you all here to cast for the tragic romantic story! First up, Romeo!" Sally continued.
Both Clarence and the Devil's eyes popped, wanting the part of Romeo.
"And the role of the beautiful Juliet." Sally finished.
Gwen's eyes popped, wanting to get the part of Juliet.
"If I'm lucky Henchman, my beautiful flower will be my Juliet and I'll give her another kiss." The Devil said.
"Duh, boss, even if you both got the roles, you know she hates your guts." Henchman reminded his boss.
"Oh, shut up!" The Devil scolded.
"I SAID QUIET!" Sally yelled.
The Devil and Henchman quickly turned their attention to Sally.
"Now everyone, come up here and get your scripts and prepare for your auditions!" Sally instructed.
Everyone gets up, goes on the stage, and grab a script. Cuphead and Mugman each want to audition for the role of Romeo. Gwen and Clarence read the balcony scene.
"O Romeo, Romeo! Wherefore art thou Romeo? Deny thy father and refuse thy name. Or, if thou wilt not, be but sworn my love. And I'll no longer be a Capulet." Gwen read the line.
"Shall I hear more, or shall I speak at this?" Clarence read.
Just then, the Devil is heard rehearsing.
"I take thee at thy word. Call me but love. And I'll be new baptized. Henceforth, I never will be Romeo." The Devil read.
"Yeah, you'll never be Romeo!" Cuphead taunted and laughed.
The Devil's eyes popped and realized the cups were here too.
"UGH! You again curtain boy! I don't have time for this! I have a lead role to grab!" The Devil said impatiently.
"Uh uh! I'm gonna be the Romeo everybody loves!" Cuphead bragged.
"No, I am!" The Devil argued back.
"No, I am!" Cuphead argued.
Both the Devil and Cuphead keep arguing until Mugman intervened.
"Will you two stop it?! You heard what Gwen said. No sabotaging each other's auditions! So, be on your best behavior!" Mugman scolded.
Mugman goes off to get ready for his audition. The Devil and Cuphead glare at each other.
Later, Sally takes a seat in the front row ready to judge the auditions.
"Let the auditions begin!" Sally called out.
Cuphead goes up first and reads aloud the lines.
"But soft! What light through yonder window breaks?" Cuphead read.
But as he raised his arm, he accidentally released his script, and it flew out of his hand and broke a window. Cuphead chuckled nervously.
"NEXT!" Sally yelled.
Mugman goes up next wearing a blindfold and reads out loud.
"It is the east, and Juliet is the sun. Arise, fair sun, and kill the envious moon." Mugman recited.
Just then, a large moon prop set hanging from the ceiling and falls on Mugman, cracking the moon open.
"NEXT!" Sally yelled.
The Devil goes up next and he appears dressed in a medieval outfit.
"She speaks. Oh, speak again, bright angel! For thou art as glorious to this night, being o'er my head. As is a winged messenger of heaven. Unto the white-upturned wondering eyes of mortals that fall back to gaze on him. When he bestrides the lazy-pacing clouds and sails upon the bosom of the air." The Devil recited, imagining he is talking to Gwen.
"Thank you. Next!" Sally called.
Clarence goes up on stage as the Devil takes notice.
"You! What are you doing here boy?!" The Devil angrily asked.
"I was gonna ask you the same question." Clarence said, unfazed.
"That lead role is mine! So, you better watch your back!" The Devil warned.
"We'll see about that." Clarence said bravely.
Clarence took his place on stage. He took a breath and thought about Gwen.
"With love's light wings did I o'er-perch these walls; For stony limits cannot hold love out, and what love can do that dares love attempt; Therefore thy kinsmen are no let to me." Clarence recited with passion.
"Thank you. Next!" Sally called.
Later, the auditions were completed as Sally gathered everyone back in the audience.
"Alright everyone! You all did a stupendous job! It was a hard decision, but I've already cast the role of Juliet while the role of Romeo I'm down to two choices!" Sally announced.
Everyone gasped as Gwen and Clarence held hands.
"The role of Juliet goes to… Gwendolyn Mae Emmons!" Sally announced.
Everybody cheered as Gwen felt shocked that she earned the lead role.
"Congratulations honey. You earned it." Clarence congratulated as he gave her a kiss.
"Yay Gwen!" Both cups cheered.
"I knew my beautiful flower would get the role. She will be mine." The Devil said evilly.
"For the final two choices for Romeo, I've narrowed down to… The Devil and Clarence Hopewell!" Sally announced.
Both the Devil and Clarence's eyes popped.
"WHAT?!" Both men asked shockingly.
"Yes. You two will prepare one more audition next Friday and whoever impresses me the most will be cast as Romeo!" Sally announced.
The Devil snickered evilly, having a plan.
"Oh boy…" Clarence said worryingly.
Gwen grew worried for Clarence, knowing the Devil will do anything to get the lead role.
After theatre class was over everybody leaves. Gwen, Clarence, and the cups prepare to teleport home when Clarence was suddenly approached by the Devil.
"Ah, Clarence buddy ol' pal." The Devil warmly greeted.
Gwen pointed her ink pen at the Devil.
"Stop right there! You will not come anywhere near him!" Gwen angrily warned.
"Relax my dear. I just wanna congratulate my worthy opponent for next Friday." The Devil assured her.
Clarence looked suspiciously at the Devil.
"Uh, sure. Now please leave us alone." Clarence said.
The Devil wrapped his arm around Clarence.
"Look, I know you and I want the same woman as well as the lead role. But maybe this'll be good for us. You know, set aside our differences, and become buddies." The Devil said, being persuasive.
Gwen glared at the Devil, knowing he was at his tricks again.
"Look Devil, I don't know what game you're playing but stop it. Now if you'll excuse us." Clarence sternly said as he freed himself from the Devil's grasp.
Gwen taps her ink pen and disappears with the group.
They arrive back at the cottage and go inside. They take a seat at the table.
"Ugh! I know what he's up to. He's gonna try get close to you so he can eliminate you for the lead role and my hand in marriage!" Gwen said frustratingly.
"Yeah, I thought that's what he's gonna do since we're tied for the lead role. But how do I prepare myself for the audition next week without the Devil trying to kill me?" Clarence asked.
"That is where we come in." Gwen said, having a plan.
Cuphead and Mugman both smiled.
"Guys, how about some good ol' pranks to our two horned fiend?" Gwen asked.
"Yeah! Yeah! Yeah!" Both cups exclaimed excitedly.
"Okay guys, huddle up." Gwen said.
The group gathers around, and Gwen whispers her plan.
Later that day, Clarence was at the radio show studio getting ready for his next episode. In his dressing room, the Devil shows up scaring his assistants away.
"Ah my friend! Getting ready for another show?" The Devil asked as he wrapped his arm around Clarence.
Clarence is unfazed and ignored him as he finished getting ready.
"Don't you dare ignore me! Answer my question!" The Devil scolded.
Clarence sighed.
"Yes. I am. Now if you'll excuse me." Clarence calmly answered.
"And now, the Inkwell Isles favorite human of The Clarence Hopewell Show: Clarence Hopewell!" The announcer introduced.
Clarence danced on stage playing his ukulele and scatting. Everybody applauded Clarence's introduction.
"Good evenin' folks! Let's get this party started!" Clarence greeted.
As Clarence was performing his show, the Devil prepared to ambush him. The Devil runs on the stage, only for him to start slipping across the stage and crashing into the jumbo sign.
"Uh oh. Looks like someone went for a slip and slide!" Clarence joked and the audience laughed.
Backstage, it is revealed that Cuphead and Mugman used floor wax to make the Devil slip.
"Whoopsies!" Both cups taunted.
Clarence continued his show until it was over.
"Thank you! You've been a wonderful audience! Good night!" Clarence ended and danced offstage.
Clarence walked up to the Devil still trapped in the jumbo sign.
"Did you have a nice slip?" Clarence taunted and patted the Devil's head.
The Devil growled furiously as Clarence ordered his security guards to get the Devil out of the sign and kick him out of the studio.
Clarence and the cups laughed as they walked away back to their homes.
The next day, Clarence was out in Inkwell City doing some window shopping when he was looking at a nice new outfit in the window. But to his annoyance, he notices the Devil standing next to him in the window's reflection.
"Afternoon boy." The Devil greeted calmly.
Clarence sighed.
"I don't have time for this." Clarence said impatiently and walked off.
But the Devil wrapped his arm around Clarence, stopping him from leaving.
"What's the rush buddy? Let's have a drink, shall we?" The Devil offered.
The Devil teleports themselves to a nearby bar and both appear sitting on barstools. The Devil orders himself a glass of scotch and orders Clarence a water with lemon.
"There you are my good man." The Devil said as he passed the water to Clarence.
The Devil sips his drink while Clarence looked suspiciously at him.
"What's this all about? The audition? Gwen?" Clarence asked.
"I just wanna wish you good luck this Friday. May the best man win for the lead role." The Devil answered.
"Yeah. Sure." Clarence said, not believing him.
Just then, a jazz band on the stage started performing jazz music and people got up and started dancing.
"Ooh! Let's dance!" The Devil said excitedly.
"Oh, no thanks. I'm not in the mood." Clarence declined and prepared to leave.
But the Devil wrapped his arm around him and pulled him to the dancefloor.
"Aw come on pal, I insist!" The Devil said as magically made his white tuxedo and top hat appear.
The Devil started dancing as Clarence stood there confused.
"Come on Clarence! I could use some company!" The Devil called.
Clarence was unsure until he caught sight of Gwen arriving in the bar. He mouthed the words 'help me' to her. Gwen winked and gave him a thumbs up, gesturing she has a plan.
Clarence looked at the Devil.
"Oh alright." Clarence agreed.
Clarence started dancing to the music. The Devil took Clarence's hand, and both started dancing together, getting the attention of all the patrons. Clarence and the Devil dance impressively together as people cheered them on.
Just then, the Devil prepares to jump and attack Clarence. As the Devil jumped in the air with his pitchfork, Gwen quickly took Clarence's hand and pulled him and danced with him. The Devil landed and started slipping on the floor and crashed in the bar.
It is revealed that Cuphead and Mugman placed two banana peels on the dancefloor, causing the Devil to once again slip and crash. After eating the bananas, the cups walked up to the Devil.
"Nice new dance shoes you got." Mugman said.
"Yeah! A new pair of slippers!" Cuphead finished.
Both cups laugh and walk away, making the Devil growl furiously.
The next day, Clarence was at the theater rehearsing his lines for the audition.
"But, soft! What light through yonder window breaks?" Clarence said his line.
Unknown to Clarence, the Devil once again attempts to get rid of Clarence. He hides backstage and prepared to drop a large sandbag on Clarence. He pulls a lever to release the sandbag, that's when Cuphead also released another sandbag. Clarence bowed to the audience after rehearsing, barely dodging the sandbags. One sandbag hits the Devil, making him slam into a wall. Both cups snicker at the Devil's pain.
Gwen clapped at Clarence's performance.
"You're ready honey." Gwen complimented.
"You really think so?" Clarence asked.
Gwen nodded as the cups joined Clarence onstage and bowed.
"Thanks fellas." Clarence thanked.
"No problem buddy." Cuphead said.
Friday finally arrived and it was time for the final audition for the Romeo role. Clarence and the Devil both prepare to audition. Sally Stageplay sat in the front row, ready to judge the audititons.
"Let the final auditions begin!" Sally announced.
Gwen gives Clarence a kiss.
"Break a leg." Gwen said.
Clarence goes on stage and starts performing his audition.
"What lady is that, which doth enrich the hand of yonder knight? O, she doth teach the torches to burn bright!" Clarence recited.
He performed his monologue and Sally is impressed with his audition.
Meanwhile the Devil prepares for his audition. He was too busy looking in the mirror he doesn't notice Cuphead quietly swapping his breath spray with another bottle. The Devil takes the bottle and squirts the stuff in his mouth.
When Clarence finished his audition, Sally applauded his performance.
"Bravo! Bravo my boy!" Sally cheered.
"Thank you, ma'am." Clarence thanked and exited the stage and rejoined Gwen.
"That was wonderful honey." Gwen complimented.
"Thanks honey." Clarence thanked and both kissed.
The Devil goes up next and a spotlight shone on him with a ladder soft to the balcony on the stage.
"But soft! What light through yonder window CROAK!" The Devil recited until he suddenly croaked like a toad.
Sally is shocked at the Devil's croaking. The Devil nervously cleared his throat and resumed his audition.
"It is the east, and Juliet is the CROAK!" The Devil recited until he croaked again.
Gwen, Clarence and the cups stifle their laughter. Sally is not impressed with the Devil's performance.
"Uh…" The Devil nervously said as he struggled to continue his audition.
Next, he reached for a fake rose in the prop bush, only to realize he grabbed a lit stick of dynamite.
"Oh no…" The Devil said worryingly.
BOOM!
The dynamite exploded in the Devil's face, making the group backstage laugh.
For a final attempt, he started to climb the ladder to the balcony. Only to realize too late, it was tampered with a cut, causing the Devil to fall and crash down and destroy the set pieces.
"THAT'S IT!" Sally yelled, finally fed up as she stormed on the stage.
"You are an insult and abomination to Shakespeare!" Sally angrily yelled and kicked the Devil out of the theater into a garbage can once again.
"Wow, she gets really angry." Clarence said.
"Yep. You never wanna get on her bad side." Gwen confirmed.
Sally walked up to Clarence.
"Sorry you had to see that, but you have displayed professionalism and honor to Shakespeare. Which is why I'm giving the Romeo lead part to you Clarence Hopewell." Sally announced.
"Whoo! Yay!" Both cups cheered as Gwen hugged Clarence.
"I knew you could do it." Gwen complimented.
"I have you guys to thank for helping me." Clarence thanked Gwen and the cups.
"Now then, rehearsals will start next Friday!" Sally reminded them.
"We'll be there ma'am." Gwen promised.
A few weeks later, it was time for the Shakespearean Festival. Gwen invites Elder Kettle, Ms. Chalice, Cordelia, her parents, Rose, William and their kids to attend the festival and watch them perform the play.
They all dress in medieval costumes including Emma and Jack. While Gwen and Clarence get ready for the show, Rose and William take the kids to do some fun festivities. They notice King of Games hosting a series of board game events along with the Queen including chess.
"Come one come all! Test your wits in our beloved games!" King of Games called.
"I was pretty good at chess in my day." Edgar said as he sat down at a chess table.
"Alright. Maybe just one game." Margarine said as she sat down at the table.
Both Edgar and Margarine play chess while Rose and William took the kids to explore some more.
Then, they notice Glumstone the Giant performing puppet shows for an audience. After his show, everyone applauds him, including Rose and William. Glumstone notices Rose as everyone was leaving.
"Hey! I remember you! You came to my mountain with your sister!" Glumstone said.
"Yeah. How could I forget you were the one who ate and swallowed my sister just so she could complete a challenge?" Rose reminded him.
"He did what?!" William asked shockingly.
"Hey, I had my little friends get her out before she was digested!" Glumstone assured him.
William gagged, feeling nauseous.
"Anyway, what brings you to town?" Rose asked.
"I'm doing my puppet shows! Kids really love them." Glumstone said as he showed off his hand puppets.
Emma and Jack giggled in their carriage, which catches Glumstone's attention.
"Ooh! You have little ones of your own?" Glumestone asked as he looked down at the carriage.
"Yeah. These are my children. Emma and Jack." Rose introduced.
"Aw. Tiny human babies." Glumstone said as he reached his large finger to them. Emma reached and felt his finger and grabbed it. Jack grabbed his finger and hugged it.
"I think they like you." William complimented.
"Thanks mister?" Glumstone asked for his name.
"William. William Smith." William introduced.
Just then, a fanfare was heard playing.
"Ooh it's time!" Rose said.
Rose and William take the twins and start heading to the theater. Only to notice her parents were playing chess.
"Checkmate!" Margarine said, claiming Edgar's last piece, winning the game.
"How did you do that?" Edgar asked shockingly.
"I have my ways." Margarine bragged.
"Mama! Papa! It's time for the show!" Rose called.
Margarine and Edgar got up from their seats and joined Rose and William to the outdoor theater. Sally Stageplay enters on the stage.
"Welcome one and all to our annual Shakespearean Festival!" Sally greeted.
Everybody applauded.
"Tonight's performance is a tale of forbidden romance which ended in tragedy. Romeo and Juliet!" Sally announced.
Everybody applauded.
"Ladies and gentlemen, I give you… Romeo and Juliet!" Sally announced as she exited offstage.
The curtains pull open with a Verona-like setting. Sally reappears in a different outfit.
"Two households, both alike in dignity,
In fair Verona, where we lay our scene,
From ancient grudge break to new mutiny,
Where civil blood makes civil hands unclean.
From forth the fatal loins of these two foes
A pair of star-cross'd lovers take their life;
Whose misadventured piteous overthrows
Do with their death bury their parents' strife.
The fearful passage of their death-mark'd love,
And the continuance of their parents' rage,
Which, but their children's end, nought could remove,
Is now the two hours' traffic of our stage;
The which if you with patient ears attend,
What here shall miss, our toil shall strive to mend."
Sally delivered the prologue as everyone applauded.
A few hours pass as they reached the final scene. Clarence pretends to drink a vial of poison and pretends to succumb to his death as Gwen wakes up on the grave and sends the Friar away.
"What's here? A cup closed in my true love's hand?
Poison, I see, hath been his timeless end.
O churl, drunk all, and left no friendly drop
To help me after! I will kiss thy lips.
Haply some poison yet doth hang on them,
To make me die with a restorative.
Thy lips are warm!"
Gwen recited sadly and kisses Clarence. She takes a prop dagger from Clarence's belt and held it in the air.
"Yea, noise? Then I'll be brief. O, happy dagger,
This is thy sheath. There rust, and let me die."
Gwen delivered her final lines as she pretended to stab herself and fall to her death, making most of the audience cry.
After the show, everyone applauded as all the cast members gathered on stage and took their bows. Sally enters and raises her arm towards the cast as they all stood up applauding.
Later Gwen and Clarence were each given compliments for their performance and flowers. Elder Kettle gave Gwen and Clarence a hug.
"That was beautiful you two." Elder Kettle said with a tear in his eye.
"Thanks, Elder Kettle." Gwen thanked.
"Yeah, you and Clarence killed it out there!" Cuphead added.
"Your love made it most convincing." Mugman said.
"Thanks fellas." Clarence thanked.
Ms. Chalice and Cordelia hugged Gwen and Clarence.
"You and Gwen were awesome handsome." Ms. Chalice complimented.
"I was literally crying." Cordelia said as she wiped her tears.
"Thanks Chalice. Thanks sis." Clarence thanked.
Gwen's family approached them.
"You were wonderful my dear. You and Clarence." Margarine complimented.
"I couldn't be prouder of you both." Edgar added.
"Thanks mama, papa." Gwen thanked.
"What say we head to that tent to celebrate; they're having that banquet!" Rose suggested.
"Wonderful idea, I'm starving." William agreed.
The family and the cups all head to the banquet together. Later, they join a dancing event as Rose and William along with Gwen and Clarence join in the dancing with other couples. Back at the outdoor theater, it is revealed that the Devil was put to work as a janitor as punishment for his failed audition as well as his attempts for killing Clarence.
"Get to work! The theater isn't going to clean itself!" Sally yelled.
The Devil groaned in agony as he continued sweeping the audience rows.
Gwen and her family and friends celebrated together and continued to enjoy the festivities until it was finally time to return home. Gwen's human family returned to the human world and Gwen and her second family return to the cottage while Clarence, Ms. Chalice and Cordelia returned to their apartment.
Gwen changed into her nightgown, put on her invisible sweater, and crawled into bed. She felt proud of herself for once again protecting Clarence from the Devil and another spectacular performance with her fiancé at her side and realized their wedding day was getting much closer.
"A glooming peace this morning with it brings.
The sun for sorrow will not show his head.
Go hence to have more talk of these sad things.
Some shall be pardoned, and some punished.
For never was a story of more woe
Than this of Juliet and her Romeo."
Gwen recited the final line and went to sleep.