If you have a dog named Benny then please continue reading. Otherwise, disregard this and enjoy the rest of my portfolio.
Hey Stephen,
If I'm being honest I've put off working on this little blurb for the past week, partly because I've been rendered inert in the wake of the show's closure, and partly because the task that I've set out for myself seems impossible. I wrote this link in the yearbook impulsively, and now I'm left with a seemingly infinite space to write rather than the confined corner of the "autographs" page. I'm reminded now that creative limitations are a gift, not a hindrance.
There's this old question that floated around the internet years ago that asked: would you rather receive a million dollars or have one dinner with Jay-Z? The question seemed ludicrous to me the first time I heard it, but even today with Mr. Roc-A-Fella's diminished reputation there are countless folks out there who say they'd choose the latter without hesitation. I couldn't help but think of this query when we had our seminar with you at the start of May. Despite months of working around you and meeting so many celebrity guests that the feeling "star-struck" became a stranger to me, there was still an aura surrounding you that I had yet to crack. Maybe it was the way that Martin from security would clothes-line me any time you were about to round a corner or the fact that I didn't do House Band or Script until the latter half of the internship- but the seminar felt like the first time I could really close that gap.
And so I said my name, hometown, and college, then asked my question.
Rather than asking for advice like some of my peers I chose to satisfy an odd curiosity about your identity: I'm paraphrasing here but it was something like "How do you manage performing a stage persona that's more in-line with your real personality, especially considering the transition from playing more of a character on The Colbert Report?" I was intrigued by your answer, and more specifically the part when you admitted the difficulty you faced on the rare occasion that you actually agreed with the Report host. But at the end of your response you made an observation about my question which caught me off-guard. You noted that at its core lied another question more veiled, that being "what's it like to be famous?", which you dismissed as a tool more than anything. Then and there I felt I saw you face-to-face.
In the weeks following our meeting I felt satisfied with what I asked, but all of a sudden I was given this opportunity to speak directly to you again and the wheels in my mind started spinning. My dinner with Jay-Z suddenly had a hypothetical second course, but what was left for me to ask?
My one remaining question (and then I'll wrap this letter), is as follows:
Can I work for you again?
My personal email is joeycacciarelli@gmail.com. If you'd like to respond then feel free to do so there.
Thank you for reading this far and thank you for establishing a work environment as special as this one. When I heard about the conversation you and Spike Jonze had back in 2015, it didn't really make sense to me how a late night show could be about love, especially when so much of the show is butt jokes and the orange man running amok in our high office. Now that I've worked with you, I know wholeheartedly what you meant.
All my best wishes,
Joey
P.S. - It was me who made the catering labels this past year. I heard you liked one of them, here are the rest: