20 Questions with Danny Pellegrino

Danny Pellegrino

20 Questions is a Q&A interview series with musicians, authors, and everyone in between, celebrating experiences both shared and individual in the messy game of being human.

“There is so much heaviness around us that it’s important to recharge our batteries with a matinee or a hike with some music. Sometimes the pop culture challenges our thoughts, and sometimes it serves as a meditation to help us relax.” Danny Pellegrino is a writer, comedian, and content creator. He is the creator and host of Everything Iconic with Danny Pellegrino, a comedic pop culture podcast available wherever you listen to podcasts.

Pellegrino has performed at The Troubadour, The Gramercy Theatre, The Laugh Factory, The Comedy Store, Groundlings, Second City Chicago, the iO theater, and more. His content has been featured in a wide range of publications including but not limited to Billboard, BuzzFeed, People, World of Wonder, Refinery29, and the Huffington Post. On television, he’s appeared on ABC News and Watch What Happens Live, and his new book, How Do I Un-Remember This?: Unfortunately True Stories, hits shelves everywhere tomorrow.

A dream comes true as Danny is this week’s guest on 20 Questions! He told me all about his new book, how pop culture is able to unite the most broken of things, the importance of working through our collective grief as well as LGBTQ+ visibility and storytelling, and so much more.

What inspired you to start your iconic podcast, Everything Iconic with Danny Pellegrino?

I had been doing stand-up and sketch comedy, and a serious bout of anxiety/depression made me think I would never get on a stage again. A friend recommended starting a podcast because I could perform from my home. I had a little following on Instagram from making memes, so I used that platform to help launch the show. I used the Instagram and podcast to help each other grow, plus I was able to satisfy the performing itch I had without the stress and anxiety of getting in front of an audience in person.

Growing up, did you always know you wanted to be a writer? Which career paths did you consider the most?

I always loved to read, but I thought I would be a television/film writer and actor. I am working in that space now, but my love of book writing came a little later in life. When I was young, I just wanted to entertain people, make them laugh, and it never mattered much to me if that was through writing, hosting, acting, or some other format. Also, I grew up OBSESSED with The Rosie O’Donnell Show, so it’s always been a dream to have a talk show like hers was in the 1990s.

If you could pick one author that’s inspired you the most, who would it be and why?

Joel Derfner wrote a book called Swish: My Quest to Become the Gayest Person Ever and I remember reading it right before I decided to come out of the closet. It was so important to me because it was the first time I read something that felt like me on the page. It was also a glimpse into a future that I hadn’t seen before, because around 2009 there still wasn’t a whole lot of gay representation in media. I had read other gay work before, but his book hit me at such an impactful time.

Favorite book of all-time?

Bridge to Terabithia. Truly obsessed at a young age. I collect different editions of it, so I have multiple copies. It’s always a great reminder to me as a writer to not be afraid of the darkness. Although it was a book written for kids, it presents death and grief in a way that is honest and unfortunately too rare, even within more adult work.

One piece of advice you’d give to your younger self?

I wish I could enjoy the stages of life as I’m in them. I tend to want to rush time and skip ahead. Be happy where you are now!

What fuels your passion for pop culture the most? What do you make of the ways that it serves as an escape while also providing an avenue through which to better understand ourselves?

Pop culture is the great unifier, particularly in the times we’re living in when we’re all so divided. I always know that I can connect with someone by asking their favorite movies, songs, or books. There’s usually something that we can find common ground on, which is what I love most about pop culture. We also need the escape. There is so much heaviness around us that it’s important to recharge our batteries with a matinee or a hike with some music. Sometimes the pop culture challenges our thoughts, and sometimes it serves as a meditation to help us relax.

What time of day are you most inspired?

In terms of writing, the inspiration can hit me at any hour. I’ve stayed up all night writing, and I’ve also been able to write at noon. For my podcast, I try to always record between 10 AM – 2 PM because that’s when I’m most wired and my brain is a little sharper. When I record at night, the jokes don’t come as easily or as quickly.

What’s the most challenging part of writing for you?

Finding the time. I feel so fortunate with some of the opportunities that I’ve gotten to explore over the last year or so, but they all take me away from writing. There have been many times lately where I want to sit and write something that’s floating around in my head, but I’m simply too tired.

Favorite social media app?

Instagram! I love Twitter because I follow a lot of hilarious people, but Insta feels the nicest overall, with a lot less negativity. And I like that I’ve curated my feed so it’s mostly dogs, male models without their blouses on, food, and Real Housewives memes.

As you explain, the decision to write a book about yourself came about after listeners online kept wanting more from the tidbits of your personal life that you’d share on your podcast. How would you describe the leap from the microphone to the page?

It was a fairly seamless leap for me. I was familiar with the publishing world after ghostwriting/co-writing two other books for other people, so I knew what to expect in terms of the process. I also felt confident in the storytelling because the podcast offered me a way to workshop a lot of what is in the book. Even stories that I never shared on the pod, I knew that they would work in the book because I had a good sense of what the audience was liking and not liking. Finally, it was a thrill to get to expand on little moments I shared on the show and flesh them out on the page. I’m SO excited for people to read about certain moments that maybe I briefly touched on during my show.

One song that you will never be sick of?

“Teenage Dream” by Katy Perry is, to me, a perfect pop song. I also never tire of anything by Queen Mariah Carey.

The last series you binge-watched?

Love Life on HBO Max. Loved season 2!

Favorite movie of all-time? Only one!

You’ve Got Mail. It is my everything.

Reading How Do I Un-Remember This? brought about memories of the time I performed Kelly Clarkson’s “I Do Not Hook Up” as my audition for my sixth grade musical and no one thought to tell me that might’ve been an inappropriate choice. What do you make of the ways that pop culture allows queer people to see themselves, even within heteronormative media?

Okay, now I need to know everything about this sixth grade audition! How did everyone react?! I think LGBTQ people often look to heterosexual stories for something to relate to, simply because there aren’t a lot of options out there for LGBTQ-led stories. I always think about how many gay men love The Golden Girls, and of course the storytelling is brilliant, but I think gay men also saw themselves in these older women, who were adults with vibrant sex lives and friendships that became family. A lot of gay men, particularly at the time, weren’t seeing stories that looked like their own, but Golden Girls was pretty close.

How would you describe the importance of storytelling, especially in an age of social isolation?

We all need to feel less alone, particularly when we’re physically solo. Storytelling helps us all feel like our experiences are valid and shared.

As a writer and artist, what would you say is the best way to rest or decompress?

Reading helps me decompress. I also like watching my favorite movies/TV shows, things that I’ve seen a million times. The Comeback, You’ve Got Mail, Moonstruck, Father of the Bride, The Nanny, Love & Basketball, Jerry Maguire, The Golden Girls…these are all things that bring me comfort and help me unwind even though I’ve seen them all more times than I can count. I also get in YouTube spirals watching old talk show clips at night. Helps me relax.

You touch on the subjects of mental health and processing grief in the book. What do you make of the current progress of dismantling the centuries-old stigma associated with mental health and what are some key areas our culture still needs to work on?

We all need to talk about our experiences more! I noticed when I started to open up about my own mental health struggles on my show, people were writing me with their own stories, which made me feel less alone. It’s so simple, but so important. In writing How Do I Un-Remember This?, I realized I may be comfortable talking about all the brain stuff, but I still had walls up when it came to grief. I tried my best to explore why that is, and I think we still have so many strides to make when talking about death. The way it’s handled is strange and unhealthy. So many of us our taught to only acknowledge loss for a short time, to get through the funerals and the wakes and then simply move on. Sometimes that might not be enough, and people shove their feelings of loss down deep where it festers. I worry about how we’ve all lost so much during this pandemic and how so few people really understand how to properly process grief (myself included). I don’t quite know what the ramifications will be, but we need to start looking at and talking about death and loss in a healthier way, in my opinion. I hope that doesn’t sound too bleak!

For you, how important is queer visibility in media and culture?

Queer visibility is SO important in media and culture. I think many people assume that just because we’ve made strides in the last 10 or so years that suddenly everything is equal, but there are still so many areas of pop culture that queer people are excluded from. I was recently talking to some friends about the National Lampoon’s Vacation movies. There have been tons of knockoffs and takes on the classic family vacation story, but to my knowledge, we’ve never seen one with two lesbian parents or two gay parents. We need these stories so that young queer people can see having a family as a viable future. Even going more broad, it’s rare to see LGBTQ representation in any family films—animated or otherwise. There are so many different stories left to tell and genres left to explore when it comes to LGBTQ representation so that people can see themselves on screen.

One thing that’s been keeping you sane throughout the COVID-19 pandemic?

Rosie O’Donnell has been posting old interviews from her talk show on her YouTube channel. She uploads one per day throughout the week. Highly recommend!

What can we expect to see next from you?

I’m hoping to do another book! After I finished How Do I Un-Remember This?, I kept writing and I’m optimistic the new stories will be part of an upcoming collection. There are some things I’m exploring in the film/TV world. One of the movies I wrote was recently optioned. We have a director and a couple of great actors attached to it, as well as there being a part for me to act in it. I’m hopeful we’ll be able to get it made, but who knows these days. Also working on adapting the book for TV and talking to some production companies about that now. There are a few other projects that I will hopefully be able to share soon!

Follow Danny Pellegrino on Twitter and Instagram, listen to his podcast Everything Iconic wherever you find podcasts, and find his book How Do I Un-Remember This? tomorrow wherever books are sold.