Staring at the face of Leonardo Di Caprio, Will couldn’t help but gape for a few seconds. He even reached out and pinched Leo’s cheek to check if he was real. 

“Dude! Are you Gay?! I thought you were in a relationship with June Roberts!” Leo exclaimed, not being able to step away because of the wall behind him. Snapping out of his daze, Will realized what he’d done and stepped away from Leo but continued looking at him.

“What is your name, kid?” He asked, ignoring his previous question.

“Uhhhh, Leonardo, sir. Leonardo De La Rosa,” Leo replied, fumbling for his words, a little weirded out by Will’s reaction.

“How old are you?” Will asked again.

“Why would you tail someone up to four blocks just to talk to them?” Will asked, finally regaining his composure from the momentary loss he’d faced due to seeing yet another famous face from his previous life.

Leo chuckled nervously and scratched the back of his head, fidgeting a little “Uhmm, yeah, uhhh, I am sorry, I didn’t mean to, you know, stalk you or anything, I mean, I did. But not like that. Ugh, I am messing up, aren’t I? Please don’t hand me over to the police.” He asked rhetorically.

Will just had an amused face at seeing someone as charismatic and talented as Leonardo Di Caprio fumbling over his sentences just because he was talking to him.

“Breathe! I will not hand you over to the cops, and I just need an honest answer.” Will tried to calm him down.

Leo breathed a sigh of relief hearing that and replied, “I saw you outside the photo studio, I work opposite the studio, in the café. I just finished high school, you see. And I saw you exit the studio, and despite the heavy clothing, I recognized you, I am a big fan, by the way. I wanted to become an actor, and so I thought that if I got to talk to you, I might have a chance at, maybe, possibly, working with you. I mean, I am not expecting a big movie or anything, just something small, maybe, I don’t know. I didn’t think this through, did I?” He trailed off in the end.

Will looked at him again, and he could see that Leo did look like he did during [Titanic], which meant that he’d need a lot of work before he could potentially match the talent he’d shown in later films like [Wolf of Wall Street], [Django Unchained] or [The inception]. But he could certainly, potentially pull off the boyish charm that had launched him to stardom after [Titanic]. 

“You know what, kid. Follow me, I want to see if you have the talent in acting required for this industry. I will give you one chance; I have a script back at my hotel.” Will informed him.

Leo’s face brightened immediately, and you could see that he was both shocked and hopeful about getting an opportunity to potentially start his career in Hollywood.

“And kid, don’t follow people up to four blocks, if people found out, your whole career would be finished before it even begins,” Will informed him, making Leo go pale.

***

Walking to The Plaza hotel, Will kept asking Leo about his life and why he wanted to be an actor. He’d found that Leo actually had worked as an extra in some Hollywood movies, mostly movies made by Krown Studios and ICM. He had hoped to land a big role in the industry, but when he didn’t, he returned to finish high school and his education and then take another shot at Hollywood. Unfortunately, he didn’t have money to keep attempting to land a shot at big movies and he had plans of starting a restaurant if it didn’t pan out.

Will wanted to check if he had the same talent that he had in his previous life. He wanted to exploit the boyish charm that so easily skyrocketed him to stardom in his previous life in the early 90s and 2000s. 

Walking up to the front desk of The Plaza, Will called for the hotel manager. He was immediately answered by a tall man of Italian descent. 

“Good Afternoon, sir! How may I help you today?” The manager asked him.

“Good afternoon, I have a suite here in The Plaza, Suite 7; I wanted to check whether the conference rooms of the hotel are empty and maybe book a conference room for the evening today.” He asked.

“Certainly, sir, the conference rooms are available now, and for this evening, would you need a catering service for the guests in the conference room?” The manager asked after confirming Will’s hotel card against the Suite registry.

“No, if they’re available now, please guide the gentleman beside me to the Conference room and send a busboy with me. I want to send a few documents to him in the room from my suite.” He requested.

“Certainly, Sir.” The manager nodded, looking at Leo, and then called for a busboy, “Istaban! Please guide this gentleman to conference room 23, and then head to Suite 7; Mr. Evans will give you further instructions there.”

The Busboy, Istaban, immediately stood by Leo and Will, waiting for them to finish their talk.

“Leo, I will send a script with the busboy to the conference room. I want you to work on it, for two hours and prepare whatever you think is necessary. I want to see the best performance that you can muster in two hours. I will see if you’re good for a role in one of my next projects based on the performance.” Will informed Leo.

Hearing his words, Will could see that Leo had become extremely nervous, but there was a glint of determination in his eyes. He knew he was placing Leo on the spot with the small amount of time he had given him, but he wanted to measure the actual talent this Leo possessed and see how versatile he could be at the moment. Based on that, he would decide how much work would be necessary for nurturing the talent within Leo.

Leo nodded to Will and said, “Thank you, sir, you won’t regret giving me a shot!” And then motioned the busboy to lead him to the Conference room.

Will watched him leave for a second and wondered whether he had hit yet another jackpot like Robert. To him, it seemed many talented actors and actresses of his previous life were still struggling to make a name for themselves in the bland Hollywood industry of this life. While Hollywood here did have some fantastically written and directed movies, over the course of the year, he had come to realize that due to the drastically different political structure in Hollywood, many aspiring actors and actresses couldn’t achieve their dreams. He intended to find as many hidden gems that he could recognize from his previous life and try to help them make a name for themselves in this version of Hollywood as well.

Heading upstairs to his Suite, which gave a rather elegant view of Central Park. He quickly searched his laptop for the final version of the script of [Liberty City], that he wanted Leo to act out. He had realized the Italian actor would make a perfect candidate for Mario Di Mauro, should he possess the same acting prowess he did in his previous life, no matter how rough it may be as of yet.

Quickly creating a separate document for Leo, removing certain scenes that he didn’t yet want him to know of, he curated a scene that should last at least five minutes while giving a good detailed picture of who the character was supposed to be. Getting the document printed, he waited for the busboy to ring the bell while he once again admired the view of Central Park from his Suite window, wondering whether he would find more talents like Leo in the coming future.

As soon as the bell rang, he opened the door and instructed the Bus Boy to hand the document to Leo and then get him a steaming cup of tea. He wanted to clear his mind and prepare for the future, if Leo performed well, he could already see [Liberty City] turning into the start of something really big for him and his company.