Another day passes in Heaven as Gwen and her friends continue hiding in her palace. They continue their usual routine with breakfast and Gwen doing college homework, Clarence rehearsing for his upcoming movie and the cups play with their toys.
After doing her homework, Gwen looked out the window at the clouds, worrying for their upcoming wedding coming much closer and the Devil was still on the move.
"You alright honey?" Clarence asked, joining her.
Gwen stood silent, saying nothing.
"You nervous for the wedding?" Clarence asked.
"No. Scared." Gwen corrected.
Clarence wrapped his arm around her, comforting her.
"I know. I'm scared too. But I also think things will still work out in the end." Clarence said.
Gwen sighed.
"I've been warned that something much worse than anything we faced before is coming. And soon too." Gwen said, recalling Quadratus's warning.
"I know. But we need to be ready for that." Clarence said.
Gwen still felt unsure. Clarence took both her hands.
"I know what'll cheer you up." Clarence said, getting an idea.
"Where do you wanna go today?" Gwen asked, figuring it out.
"I have the perfect romantic place in mind this time." Clarence said with a smile.
"You don't mean…?" Gwen was about to ask.
"Oh yes." Clarence said.
"Italy." Both said at once.
"Oh. Heh heh." Gwen said, recalling her 19th birthday when the Devil took her to Rome.
"We could maybe go to Rome, Venice, Sicily, the ruins of Pompeii, the Coliseum, and maybe that famous art museum you want to go in Ferrara." Clarence said, laying out the details.
"The Palazzo dei Diamati to be exact." Gwen said.
"Yeah, that one." Clarence confirmed.
"Okay, okay. You win." Gwen said.
Just then, they felt 3 pairs of arms wrap around the couple.
"Hey fellas." Gwen greeted.
"You better not leave without us." Cuphead said.
"Cuphead, she knows better than to abandon us." Mugman reminded him.
"Yeah ding-dong." Ms. Chalice agreed.
"We were just waiting for you." Clarence said.
Gwen tapped her ink pen, and they disappeared. They appear in the city of Rome.
"Wow, where are we?" Cuphead asked.
"Welcome to Italy. We're in city of Rome." Gwen answered.
"Italy?" Mugman asked.
"Rome?" Ms. Chalice asked.
"Yep. This is where pizza and other delicious food was invented." Clarence added.
"Pizza!" Both cups exclaimed.
"Yum, pizza sounds good right now." Ms. Chalice agreed.
"We'll have pizza this afternoon. But first, time to fly." Gwen said as Cerulean Bolt flew out of her satchel.
The group hop on, and Cerulean Bolt flies up in the sky.
"There's the Coliseum!" Clarence said and pointed.
They fly over the massive Coliseum.
"What'd humans do here?" Mugman asked.
"Long ago, there were gladiator fights where they fought to the death for entertainment." Gwen answered.
"Yeesh!" Both cups groaned and cringed.
"Why didn't they just play soccer or some fun sport?" Cuphead asked.
"Because soccer wasn't invented till way later." Clarence answered.
"Boy, those people were messed up with how they got entertainment." Ms. Chalice said.
"Okay, moving on." Gwen said.
They fly and notice a tower leaning.
"Why is that tower leaning?" Mugman asked.
"That is called the Leaning Tower of Pisa." Gwen answered.
"Ooh! Is that where the pizza is?" Cuphead asked.
"Not pizza you dumdum! Pisa!" Mugman argued.
"Guys enough." Clarence scolded.
Gwen shook her head as they moved on. They pass various sights of the Trevi Fountain, the Pantheon, various churches and palaces.
Next, they fly south to the Palazzo dei Diamati in Ferrara. They look at the beautiful Re paintings from the Middle Ages and the 18th century.
"Really old paintings they have from long ago." Clarence said.
"Yep, Italy has really talented artists from way back." Gwen said.
After their tour of the museum, they continue traveling south until they reached the ruins of Pompeii where crumbled building and corpses covered in ashes were present.
"Woah, what happened here?" Ms. Chalice asked.
"A long, long time ago, a volcano called Mount Vesuvius erupted and wiped out the town of Pompeii. Nobody survived." Gwen told the story.
"Wow, nobody was lucky that day." Mugman said.
"Yeah. Those poor people settled in the wrong place." Clarence agreed.
"Is that the volcano up there?" Cuphead asked pointing up.
The group looked up and saw the volcano still standing.
"Yep, that's Mount Vesuvius. We can't go there. That place is forbidden for a reason nowadays." Gwen said.
"Phew!" The cups sighed of relief.
The group continue flying south until they reached the Italian island of Sicily. They arrive at a famous beach called Isola Bella and settle on the white sandy beach.
"Hey guys look! Boat tours!" Mugman exclaimed.
They looked and noticed a group of tourists on a boat traveling through a cave.
"Wanna check out the Blue Cave?" Gwen asked.
"Yeah!" All three cups exclaimed.
They hop on Cerulean Bolt and fly inside the Blue Cave.
"Woah!" The group exclaimed as their voices echoed.
"No wonder it's called the Blue Cave. It's blue inside!" Mugman said.
They continued flying until they reach outside of the cave and return to the beach.
"Okay, wanna grab pizza?" Gwen asked.
"Yeah!" All three cups exclaimed.
They travel in town and find a local restaurant and order an extra-large supreme pizza for all of them to share with breadsticks and Caesar salad.
"This is the best pizza I've ever had!" Cuphead complimented as he was eating.
"Ditto to that!" Mugman agreed.
They grab their glasses of Italian sodas.
"To another day of fun in paradise." Gwen toasted.
They clinked their glasses and drank the Italian soda. Afterwards, they have biscotti cookies for dessert.
After lunch they travel to a local gift shop and purchased Venetian masks, little wooden puppets of the fairy tale character Pinocchio, Italian chocolate and small Murano glass.
They leave the gift shop until Clarence noticed something around his neck. He discovered a beautiful golden necklace.
"Gwen, did you make this for me?" Clarence asked.
"Maybe." Gwen quickly said with a smile.
"Thanks honey, you didn't have to." Clarence thanked.
"I wanted to. Because your heart is the real gold." Gwen said as Clarence smiled.
They continued walking down the streets until they noticed a local female painter painting on a large canvas on the side of the street. Gwen takes a peek and notice the girl painting the Isola Bello with the beach and the town.
"Ciao, ti piace il mio dipinto?" The girl asked in Italian.
"Uh…" Gwen wasn't sure what she said.
"Parli italiano?" The girl asked.
Gwen shook her head, still not understanding.
"You speak English?" Gwen asked.
"SÌ. I speak English." The girl answered.
"Oh good. What did you ask me?" Gwen asked.
"I asked if you like my painting. It is my latest work." The girl translated.
"Oh, yes. It's beautiful. The colors, the details, the likeness." Gwen complimented.
"Grazie." The girl thanked in Italian.
"What's your name?" Gwen asked.
"My name is Ortensia Vendelini. What's yours?" Ortensia introduced herself.
"Gwendolyn Mae Emmons. Call me Gwen." Gwen introduced herself.
"You are American. I can tell by your accent." Ortensia said.
"Yeah. Are you from here in Isola Bella?" Gwen asked.
"No, I come down here to finish my painting. Then I return home to Messina." Ortensia explained.
Just then, Clarence and the cups approached the women and look at the painting.
"Beautiful." Clarence complimented.
"Grazie." Ortensia thanked.
"Oh, sorry dear. I was just chatting with Ortensia here. She paints beautifully." Gwen explained.
"It's okay. Really nice painting she has." Clarence said.
"I have an art exhibition show coming up if you and your…" Ortensia was about to say until she noticed the cups.
"Oh mio Dio! What are they?" Ortensia asked shockingly.
"Calm down. These are my best friends Cuphead, Mugman and Ms. Chalice. And this is my fiancé, Clarence Hopewell. We're getting married soon." Gwen introduced.
Ortensia looked at the cups with fascination.
"Yeah, we know. We have cups for heads." Cuphead said.
"Tazze." Ortensia said.
"Tazze?" Mugman asked.
"Cups in Italian." Ortensia translated.
"Oh nice." Ms. Chalice said.
Ortensia then remembered the time and packed up her painting supplies and safely placed her canvas into a bag.
"I just remembered. I have to get home to my mama and papa." Ortensia said.
"Oh, well it was nice meeting you Ortensia. Good luck with the art exhibition." Gwen said.
"Wait, I was wondering if you and your friends want to attend? I could use some new faces to impress the art collector who is shopping for a new museum." Ortensia asked.
"An art collector?" Ms. Chalice asked.
"SÌ. If he is impressed with my art, he'll buy some and make me famous in his museum. Also to help my family from going poor since times have been bad. My art has to help bring us out of that." Ortensia explained.
The group looked at each other. After quietly discussing, they reached a decision.
"Okay, we'll attend your art exhibition." Gwen said.
"Perfetto! Let's go! There's a bus leaving soon to Messina!" Ortensia said excitedly.
The group follow Ortensia to a local bus stop only to realize they were too late as the bus left.
"No! Come back!" Ortensia called.
"Oh, maybe we can wait for the next one?" Clarence asked.
"No, the art collector will be at my home in a couple of hours and I have to get home fast!" Ortensia said feeling panicked.
"Hey, hey. Calm down. I have a solution." Gwen calmed her.
"You do?" Ortensia asked, confused.
Gwen summoned Cerulean Bolt and flew in front of Ortensia, making her gasp.
"Don't freak out, he's friendly." Mugman said.
"He?" Ortensia asked.
"This is Cerulean Bolt. My magic carpet." Gwen introduced.
Cerulean Bolt shakes hands with Ortensia.
"Wow. Un tappeto magico." Ortensia said in Italian.
The group hop on, and Gwen reached her hand to Ortensia.
"Come on, it's okay." Gwen assured her.
Ortensia hesitated but then remembered the exhibition and hopped on.
"To northwest!" Gwen ordered.
Cerulean Bolt flies in the air, making Ortensia scream.
"Hey, no screaming. It hurts our ears." Cuphead said, making her stop.
"What is this magico?" Ortensia asked.
"Yeah, I'm what you call 'magico.'" Gwen answered.
They flew until they reached Messina.
"Where's your house?" Gwen asked.
Ortensia looked and then pointed to a little yet pretty house.
"Down there." Ortensia answered.
They flew down to the front door and stepped off.
"Wow. That was amazing." Ortensia said.
"Yeah, you get used to it after a while." Mugman said.
Ortensia opens the house, and they enter inside.
"Mama! Papa! Sono a casa!" Ortensia called in Italian.
"Sono in cucina!" An older woman called.
"Are you sure your parents won't mind?" Gwen asked.
"Yes, Gwen. Mama loves the extra company." Ortensia assured her.
They enter the kitchen.
"Mama, abbiamo ospiti." Ortensia announced.
The older lady turned around and is shocked at the guests before her.
"Oh, mio Dio!" The older woman exclaimed.
"Va bene mamma. Sono amici." Ortensia calmed her.
The group looked at them, having no clue what they said.
"Anyway, this is my mama, Lucia Vendelini." Ortensia introduced.
The group waved at her.
"Mama, questi sono i miei amici Gwen, Clarence, Cuphead, Mugman e Ms. Chalice." Ortensia introduced.
"Ciao." Lucia greeted.
"Ciao. I hope we're not intruding on your home." Gwen said nervously.
"Don't worry Gwen. You are here for the exhibition." Ortensia assured her.
"Ortensia!" An older male voice called.
The group looked and saw an older man with a broom enter the kitchen.
"Chi sono questi estranei?" The older man asked.
"Papa, sono venuti per la mostra d'arte." Ortensia answered.
The group still had no clue what they were saying.
"This is my papa, Lorenzo Vendelini." Ortensia introduced.
The group waved at him.
"Papa, questi sono i miei amici Gwen, Clarence, Cuphead, Mugman e Ms. Chalice." Ortensia introduced.
Lorenzo looked at them.
"If they are here for art exhibition, they will help us set it up." Lorenzo said in English.
"Oh, you speak English." Clarence said feeling shocked.
"English, I knew it." Cuphead said.
"You two, help mama with the food. And you strange children, help me clean up. We have important guest coming over." Lorenzo ordered.
"Aw, do we have to?" Cuphead complained.
"Cuphead! We want these people to like us! So do as he says!" Gwen quietly scolded.
"Fine." Cuphead said as he grabbed a broom and started sweeping.
Ms. Chalice grabbed a duster and Mugman grabbed a cloth and cleaner spray. Gwen and Clarence help Luisa with the cooking and helped plate up all the delicious food.
A couple of hours later, the house was clean, the table was set up and the art canvases were on display.
"Wow, we did it. Everything's ready." Ortensia said.
"Yeah, this art collector is gonna love this." Cuphead said.
"Now remember guys, best behavior when the art collector gets here." Clarence reminded him.
"You got it handsome." Ms. Chalice agreed.
Just then, they hear a knocking at the door.
"Oh! That's him! Everyone to your places!" Lorenzo instructed.
Everyone took their positions as Ortensia opened the door. There stood an older well-dressed man smoking a cigar.
"Saluti Mr. Anthony Gandolfini. Ci aspettavamo te." Ortensia politely greeted.
"Ciao, Ms. Vendelini. I trust you have your art pieces ready?" Anthony asked as he blew smoke.
"Sì, vieni subito." Ortensia said and gestured him to come in.
Anthony entered the house looking around, noticing the clean house.
"Very small yet very clean house you have." Anthony said.
"Grazie." Ortensia thanked.
Anthony enters the family room where everyone smiled.
"And who are your visitors? Here to look at your art collection I assume?" Anthony asked, noticing the cups.
"Sì, Mr. Gandolfini. And this is my mama and papa Lucia and Lorenzo Vendelini." Ortensia introduced.
Anthony approached Cuphead, Mugman and Ms. Chalice.
"What strange beings with cups for heads." Anthony said.
Gwen gave a glare to Cuphead, gesturing him to be polite.
"H-h-h-hello." Cuphead greeted nervously.
"Oh, you do speak." Anthony said, shocked.
Ms. Chalice was about to say something until Clarence shot her a glare to keep quiet. Anthony looked at Mugman then Ms. Chalice.
"What are your names?" Anthony asked.
"They are Cuphead, Mugman and Ms. Chalice." Ortensia introduced.
"Extraordinary." Anthony said.
"Grazie." Ms. Chalice thanked and gave a curtsey.
Gwen gave a nod of approval.
"Prego." Anthony said.
He stood up and started looking at the art displays. His face remained unreadable as he observed each painting one by one.
"Very good. Excellent choice of colors, details and likeness." Anthony said his thoughts.
Ortensia watched with anxiety if he will buy her artwork. Gwen held her hand, calming her. Anthony turned to Ortensia and Gwen.
"Ms. Vendelini, very wonderful display of art." Anthony complimented.
"Grazie." Ortensia thanked nervously.
There was a pause of silence with growing anticipation.
"I believe these will do wonderfully in my new collection." Anthony gave his verdict.
Everyone smiled.
"Oh, grazie Mr. Gandolfini! You won't be disappointed!" Ortensia said excitedly.
"I know you won't." Anthony said.
"Mr. Gandolfini, would you like to stay for dinner?" Luisa politely asked.
Anthony looked at the well-set table with the food prepared and ready to serve.
"Why sì, I have not eaten yet. Grazie Mrs. Vendelini. The food smells delicious." Anthony agreed.
Everyone sits down as Gwen and Ortensia served pasta, bread and vegetables to everyone and sit down. Then, they poured glasses of red wine except for the cups who were too young for alcohol.
Cuphead attempted to eat first.
"Psst! Not yet!" Gwen whispered.
"Oh, sorry." Cuphead apologized.
"Let us pray." Lorenzo said.
Everyone clasped their hands together in prayer, Gwen gestured the cups to clasp their hands.
Lorenzo delivered a prayer in Italian until he said 'Amen.'
"Amen." Everyone said.
Everyone started eating and enjoying themselves.
"Oh, where are my manners? I haven't learned your names." Anthony said, referring to Gwen and Clarence.
"Oh, I am Gwendolyn Mae Emmons. And this is my fiancé, Clarence Hopewell." Gwen introduced.
"Very charmed. You are an artist yourself?" Anthony asked.
"Yes, I am studying art at college." Gwen answered.
"Excellent. You like Ms. Vendelini's artwork?" Anthony asked.
"Oh yes sir. She paints beautifully." Gwen complimented.
"You have an eye for beauty in art." Anthony said.
"Thank you, sir." Gwen thanked.
Just then, there was knocking at the door.
"Another guest?" Lucia asked.
"I'll answer it." Ortensia said.
She gets up and heads for the door. She opened it and saw an older American man standing outside. But something about him unsettled her.
"Ciao, may I help you?" Ortensia nervously greeted.
Suddenly, she was slapped and knocked to the ground.
"ORTENSIA!" Lorenzo yelled.
The man stormed into the room, making Gwen and Clarence's eyes widen in horror.
"H-H-H-Harry!" Gwen exclaimed.
"No!" Clarence exclaimed.
Clarence's disowned father Harry Hopewell arrived with vengeance. He reached for Gwen, grabbing her arm and pulled her away.
"Gwen!" Cuphead cried.
"Stay back! You follow; she dies!" Harry threatened.
Clarence grew furious, bravely stood up and approached him.
"Take your hands off her!" Clarence yelled.
"Do I have to kill you this time son?" Harry angrily asked.
"Son? He's your father?" Luisa asked.
"Never has, never will." Cuphead answered as he and the cups prepared to fight.
Suddenly, Harry felt something bite him on the leg.
"OUCH!" Harry cried in pain.
Mugman bit him on the leg, forcing Harry to release Gwen as she ran to Ortensia's aide. Clarence delivers a punch to Harry's head, preparing for a fight. The two men fought to everyone's horror until Harry finally pins Clarence to the floor.
"Now I know why the Devil wants her alive. But he was also specific about you." Harry revealed.
"She will… never be his! I love her!" Clarence yelled as he struggled.
"You know, all of this could've been prevented if you helped me get out of Hell, but you abandoned me to suffer and chose her." Harry scowled.
"Just like you abandoned me after I was born and tried to have me killed?!" Clarence angrily shot back.
Harry pulled out a gun and aimed at Clarence's head.
"Now, I'm going to do what I should have done 21 years ago. Say hi to your mom for me." Harry said, preparing to pull the trigger.
Suddenly…
WHACK!
An empty wine bottle broke against the back of Harry's head, knocking him out cold. Ortensia is revealed to have knocked him out as she caught her breath. Ms. Chalice moved Harry's body off Clarence as he got up and looked at his insane father.
Gwen quickly hugged Clarence.
"Are you alright? Are you hurt?" Gwen asked, checking for injuries.
"Just a few bruises but I'll live." Clarence said.
"That was brave of you handsome." Ms. Chalice said hugging him too.
"My boy, you lay on couch and rest. I will call police." Lorenzo said.
"No, I have a better idea." Anthony said, stopping him.
Luisa tended to Clarence's injuries.
Anthony grabbed the house phone and dialed a number and talked to someone in Italian. Afterwards he hung up.
"Who'd you call?" Ms. Chalice asked.
"I called some friends little Chalice. They owe me a favor." Anthony answered.
Clarence's eyes widened, having a good idea who he called. Just then, a knock was heard at the door.
"I'll take this one." Anthony said.
He opens the door, and two scary looking men dressed in nice suits entered the house. Anthony explained the situation and pointed at Harry. The gentlemen nodded and lifted Harry's body, tie him up and cover his mouth with a cloth gag. They stuff him in the back of their car and drive away.
"Who were those guys?" Mugman nervously asked.
Anthony gave Mugman a blank stare.
"Oh, sorry sir." Mugman apologized.
"It is alright son. Let's just say they are friends of mine who owed me a favor." Anthony hinted.
"Got it." Mugman said, nodding.
Clarence approached Anthony, feeling a bit better.
"Mr. Gandolfini, thank you for dealing with him. He's just the man who got my mom pregnant with me, but he was never my father at all, and my mom unfortunately died after I was born, and he wanted me dead." Clarence thanked and explained.
Anthony placed his hand on Clarence's shoulder.
"He is not the definition of the word 'father.' I have loving wife and beautiful children of my own." Anthony explained, revealing he is a husband and a father himself.
Clarence gave a small smile.
"You are engaged to Ms. Emmons here." Anthony said, figuring it out.
"Yes sir." Gwen confirmed as she held Clarence.
"I trust you two want children of your own?" Anthony asked.
"Yes sir. But I will never be like Harry. I want to be there for my kids. Love them, guide them, raise them and protect them." Clarence promised.
"Very good my boy. You are not that parasite." Anthony said, feeling proud.
Anthony turned to Ortensia.
"As for you Ms. Vendelini, I am still on to buy your art. That final attack on our unwelcomed guest was brilliant. You have a bright future ahead of you." Anthony said, still willing to buy her art.
"Oh, thank you sir. I won't let you down." Ortensia thanked.
Everyone smiled as Ortensia smiled at Gwen.
"Grazie Gwen." Ortensia thanked.
Gwen nodded.
As time went on, Ortensia's art is displayed in the new art museum collection and is getting fame from all around Italy. Anthony commissions Ortensia to do another painting of a beautiful woman. Ortensia gets an idea and pulls out Gwen's business card.
Later, Gwen returns to Italy and meets up with Ortensia in her art studio.
"So, what do you need from me?" Gwen asked.
"Mr. Gandolfini wants me to paint a beautiful woman for his collection. So, I want you to be my model." Ortensia said.
"Wow, I've never been a model before." Gwen said.
"All we need is for a beautiful dress and have your hair styled." Ortensia said.
Gwen smiled, getting an idea. She magically transformed into her celestial form and her goddess dress. Ortensia gasped in shock at the sight.
"You… you really are magic." Ortensia said staring in awe.
"Yeah. That's why Harry was after me. I have great power and magic the Devil wants from me." Gwen explained.
"Wow. I am sorry." Ortensia said, showing sympathy.
"Thanks." Gwen thanked.
"Now, stand up there, make a pose and I'll get started." Ortensia instructed.
Gwen stood up on a pedestal, raised her arms up as her hands glowed.
"Perfect! Don't move!" Ortensia instructed.
Ortensia started with her painting a very tall canvas as Gwen did her best to stay still.
Sometime later, Gwen and her friends join Ortensia and her parents at the unveiling of the new painting in Anthony's collection in the museum. Anthony pulls the curtain, and it reveals a tall painting of Gwen in her celestial form in her goddess dress. Everyone gasped in awe and gazed at the painting. Ortensia walked in front of the painting.
"Ciao. My name is Ortensia Vendelini, and I painted this. I believe you would all like to know what made me paint this. I learned from my friend the importance of helping other in need just as she did for me. She was a light who showed me there is still good in this world. I want to show people that too." Ortensia explained.
Everybody applauded at Ortensia's speech. Gwen and Clarence walked up to Ortensia and Anthony.
"That was a great speech, Ortensia. I was really moved." Gwen complimented.
"Grazie, Gwen. You inspired me. Mr. Gandolfini here is planning to have me teach art to other people." Ortensia said.
"Sì, your fiancé is a brave man. Willing to take a bullet for you. That's a real man." Anthony complimented.
"Thank you, sir." Clarence thanked.
"And thank you." Anthony said.
"For what?" Clarence asked.
"Aside from your fiancée, you also showed me there is still good people in the world." Anthony said.
"Oh, thank you." Clarence thanked.
"And do not worry. I had my friends take care of the man who got your mother pregnant. He can tell your mother 'hi' himself." Anthony assured him.
Gwen grew worried, knowing Anthony somehow had connections to a powerful Italian mafia.
It is revealed that the mobsters had Harry killed and buried in an unknown location.
However, the Devil caught on to this and magically took his body back to Hell, resurrected him and imprisoned him once again as punishment for his failure.
The Devil looked angrily at Harry in a dungeon cell.
"You failed me once again. And now you're permanently bound here for all eternity." The Devil said coldly.
The Devil walked away and returned to his throne room to sit on his throne. Henchman brings his boss a cup of tea.
"Here's your favorite tea boss." Henchman said, handing him a cup.
"All those human pawns failed me. I don't need them anymore; I'll make that teenage girl spill the beans on Gwen's hiding place." The Devil said, tapping his magic mirror revealing Maile working as a waitress at a local café and going to high school.
"Once everything's ready, my plan will be put into motion." The Devil said evilly.
"Aw jeez." Henchman said worryingly as the Devil laughed evilly.
After saying goodbye, Gwen and Clarence return to Heaven back to the cups. They continue to live in hiding while also doing good deeds for people in need around the world.