Danny Pellegrino Is Already in the Holiday Spirit With 'The Jolliest Bunch'

CUL PS Danny Pellegrino
Danny Pellegrino. Brian Kaminski

"It's so important to just sort of celebrate the things that you love, because you'll find the community of people who also love those things."

If there's one thing Danny Pellegrino, host of the hugely popular Everything Iconic podcast, is ready for, it's the holidays. "I'm a festive person. I love decorating for whatever holiday it is. I'm a huge fan of table scaping." And after the success of his bestselling first book, How Do I Un-Remember This? Pellegrino decided to lean into his love for the holidays with his new book of essays, The Jolliest Bunch (Sourcebooks, October). "It focuses on the Christmas holidays, but there's a Halloween chapter in there, there's some Thanksgiving, all sorts of stuff." And it certainly wasn't difficult for Pellegrino to find sources of inspiration for the book. "The holidays are so filled with emotion that there's so many stories." He "just wanted to make sure that there was a balance of really funny, heartfelt and a little drama." It's the heart Pellegrino brings to his stories which is what makes this book and everything he does so successful. "It's so important to just sort of celebrate the things that you love, because you'll find the community of people who also love those things."

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Editor's Note: This conversation has been edited and condensed for publication.

One of the things I love about your podcast is that, because of your deep love for pop culture, it's like I've found my other half, my BFF. Do you get that from listeners?

You know, I noticed with my podcasts, people coming up to me when I would go on tour or wherever listeners would see me, they would tell me that they had similar stories where they liked something that I thought was so obscure that I talked about on the show that they also really loved. That made me realize early on in the podcast run it's so important to just sort of celebrate the things that you love, because you'll find the community of people who also love those things, because you just naturally gravitate toward each other the way you and I have gravitated toward each other.

How did the podcast come about?

I was doing stand-up and sketch comedy around town in Los Angeles and really struggling with my mental health. I had fallen into a pretty deep depression. I had said I was never going to perform on stage again; I thought I just couldn't even get up on a stage in front of people. And a friend was like, "You should start a podcast because you can do your show from home, you could perform your bits from home and you just need a microphone and yourself." It took a little while for me to get the courage to actually record an episode, but I did at the end of 2017, and it sort of snowballed from there. But it came out of me thinking that I could never perform again or be in front of people in that way on a stage and, and oddly enough, the success of the podcast has led me to tour the podcast and get to meet people on stage. It really opened up so many doors at a time I thought everything was closed. And so I feel so grateful to the podcast.

I am sometimes blown away by how often you do the podcast solo. Just you talking to people. That is so hard. How do you prepare for something like that?

I don't know. I'm just used to it now that it doesn't take as much. I think early on, I was maybe scared to do these episodes where it's just me alone because my show is about 80 percent of me recapping reality TV. Early on, it was hard for me to book guests. I didn't have a Rolodex to book people, so I had to either adapt and do my show where it's just me, or I wouldn't be able to do the show. So I quickly just kind of found the way that works for me. I know some listeners really liked the episodes where it's just me talking, and then other people probably prefer when I have interviews and guests on, but I always just try to be authentic and enjoy what I'm doing. I try to recap the shows that I enjoy recapping, so I don't recap everything. I just try to pick one or two shows at a time and then also sprinkle in those interviews with celebrity guests throughout. But I have fun doing it on my own. I can't imagine doing it any other way.

What are some guests you're dying to have on?

Meg Ryan is at the top of my list. She is just the best. I love her. You've Got Mail is my all-time favorite movie. She's given us so much—When Harry Met Sally, Sleepless in Seattle, I mean, I could go on and on. And I also think she has a really interesting story. She hasn't talked to press all that much, and I think it's fascinating how the media treated her from about 2008 and beyond. I think it's terrible how she was treated, whether it be her looks or relationships, or just her personal life. So I would love to talk to her. Mariah Carey is also a favorite of mine. I ask all my guests their favorite Mariah Carey songs, so I would love to get to talk to her. But I kind of like any—name a woman in the entertainment industry that's over 40 and I probably would love to talk to them. Those are the most interesting people. It's unfortunately a male-dominated industry, so I like when a woman has outwitted and outlasted in the industry for a long period of time. I think they have the most interesting stories, they're the most fun to talk to and I tend to gravitate toward their content the most. I'm probably going to be rewatching a Meg Ryan movie on a Friday night rather than whatever the new Netflix thing is.

I'm the same way. The things I love and watch all have strong female leads. Sometimes I have to actively be like, men exist, men exist. Focus on some men.

See, I don't feel like I have to. If I'm interested in them, then I'll tell them. And sometimes, as I'm sure you notice, sometimes you might have a guest that you know that the audience wouldn't be interested in, but you love. What's fun about that is that sometimes that translates so the listener might not have been interested in the guest, but they listen and because of your enjoyment of the interview and that person's work, they become a fan. You and I both love The Rosie O'Donnell Show. And the thing I always go back to with her show was she would have guests on that weren't popular, that had been in the industry for a while, but young people didn't know. I just posted a clip of an episode that she put on her YouTube channel, it was Lauren Bacall and NSYNC. The whole audience is loaded with NSYNC fans, are screaming, they've taken off school to see NSYNC. So the fever was high. And she makes the whole audience sit through an interview with Lauren Bacall. That's two segments and a video package. And she even says [something] like, "I had Lauren Bacall on the show once but I'm having her back on for two whole segments because we didn't have enough time." And that all happens before anything. So long story short, I think she did that so beautifully, and I always try to hang on to that; follow your own gut of what you like and and then maybe the listeners or the viewers or whoever will like that person and [it] might make them become a fan.

I feel the same way about Rosie. Her interview style and how she approached being a public personality is the basis for everything I try and do. She was always a fan first and was eager to introduce the things she loved to everybody else.

Yeah, and I think people respond to the emotion and the genuineness. There have only been a few times that I've had guests that I wasn't interested in, maybe doing it as a favor, PR person reaches out to me, and it's a big name or something. There's only been, I'd say under five in the six years that I've been doing the podcast, and I always feel like those are the worst ones. And it might be a big name. But if my heart wasn't in it, it's like, what did I do that for? So I am fortunate enough that 80 percent or so of my show is just me, that I don't have to have guests on all the time. So I just try to have the people I really like on and not worry about too much else. If somebody doesn't like it, they just will listen to the next one. And hopefully we'll get them on the next one. I think it's important to have at least some sort of passion for who you're interviewing, otherwise, what's the point? No one's really going to get anything out of it, including the listeners, myself, whoever.

Your new book, The Jolliest Bunch, is all about the holidays. Now I know you're very into Christmas, but are you into all holidays?

I'm a festive person. I love decorating for whatever holiday it is. I'm a huge fan of tablescaping, which I know is so gay of me. It's so relaxing to go into the dining room with all the stuff I got from Home Goods and just rearrange and figure it out for each holiday season. But yeah, my book is called The Jolliest Bunch, and it focuses on the Christmas holidays, but there's a Halloween chapter in there, there's some Thanksgiving, all sorts of stuff. I love the holiday seasons and there are times I hate the holiday season. I think this book is for those people, too. I know it can be a stressful time and it can be a lonely time and an exhausting time. I wanted the book to be for all of those people: If you love the holidays, hopefully you'll pick it up and feel joy and you'll be thinking about your own family memories. And if you hate the holidays, hopefully you'll be just able to sit by the fire and laugh and have a good time reading these chapters.

Danny Pellegrino Jolliest Bunch
The cover of Danny Pellegrino's latest book, 'The Jolliest Bunch: Unhinged Holiday Stories' from Sourcebooks. Sourcebooks

You're right, it's not just a cheery holiday book. There are some funny alternative takes to the holidays. Was it difficult to narrow down what stories you wanted to tell?

I didn't find it difficult narrowing it down. I wrote a book that came out last year called How Do I Un-Remember This? and as I was writing that, I found that a lot of the stories I wanted to tell in that book were holiday themed. So I just kept writing. I think the holidays are so filled with emotion that there's so many stories, so I didn't feel like it was hard to cut them down. But I just wanted to make sure that there was a balance of really funny, really heartfelt and a little drama. I like that in any sort of thing that I consume. I like when stuff is mixed and you're having a really good time and then all of a sudden it hits you with something that gets you in your feels or hits you with something romantic or hits you with something dramatic. So I was mostly focused on, do I have those layers? Because I think those make up the holidays. I think loneliness is a huge thing for the holidays. I didn't want to ignore that or pretend that doesn't exist. And so I just wanted to be able to explore all those different facets. I'd say that was the most challenging part.

Is there a story from the book that particularly stands out to you?

There's a chapter that opens the book about my mom and Christmas Eve, and she has this sort of meltdown—she has this meltdown every Christmas Eve as I think most moms and dads or whoever's kind of in charge of the holiday do. So I love that chapter because it reminds me of my mom. As I was putting the book together, I noticed that there were all these stories about Santa Claus and so many movies about Santa Claus and I thought, well, there's not much about Mrs. Claus. So I had this fantasy of what does she get up to? I wrote a whole chapter that's a fictional take on Mrs. Claus. She takes the sleigh on Christmas Eve and goes to Vegas with her girlfriends. They have a debaucherous night in Vegas. It's sort of like Bad Santa with Mrs. Claus or like The Hangover or something like that. It's very raunchy and silly. I loved writing that because it got me able to explore a different side of my writing. But I was just talking to a friend, there's a chapter about this book Now and Then [which was based on] a movie called Now and Then, and when I was younger, I wanted [this book] from the Scholastic Book Fair. I had ordered it at the holiday Scholastic Fair and something else had been delivered and I was devastated at the time. But there's a chapter about that whole thing that I I think encompasses the heart and also the silliness of the book.

When I was a kid, I saw my dad putting out presents on Christmas Eve naked and it fully ruined the fantasy of Santa for me. When did you stop believing in Santa?

Very early on. I remember my mom would write on the present, it would say, "From Santa," but it was her handwriting very clearly, the only difference is she would make all the letters of the word Santa capitalized. It was still the same pen, the same everything. But then I remember trying to hide it and hold onto the Santa. So even though I knew for a year, for a couple of years, I remember trying to still pretend when my mom would hand me the gift that said "Santa." I don't even think it was for me, I didn't want to let down my parents down. I'm always so worried about somebody else's feelings.

I'd keep up the Santa gig just for the presents.

Wait, do you have a favorite gift that you received?

Oh, wow, that is a great question. One year my mom gave me a VHS combo TV. I was a Blockbuster kid. I lived at Blockbuster. So that was a big gift. What about you?

Well, by the way, I just saw on YouTube you can like watch videos of Blockbuster in the '90s. Just people casually strolling through Blockbuster in 1993. But, there was one particular Christmas that I had wanted the 101 Dalmatians plush. The movie had been rereleased or something and I wanted it so badly. And I had gotten the stuffed animal and then my brothers had gotten the Nintendo. But I remember it was like the best Christmas because they set up the Nintendo. I remember seeing it on the screen and being mesmerized by Super Mario and we played all day. So even though that wasn't my gift, I was just holding my plush stuffed animal while we all played video games, and it just sort of sticks out.

I feel like how we approach the holidays changes after we leave our families. How have you adapted the holidays for you outside of your family?

It's still changing. I think the pandemic was a change for everybody as well. My boyfriend and I have lived together for a handful of years now and we try to come up with our own little things. But it's forever evolving. I think it's so fun to reminisce. And that was one of the fun things about writing this book was being able to reminisce about those times from my childhood that I want to hang onto for when I have kids or as I move into my own adult life. I was exploring those things that I wanted to do and the things that maybe I looked at and was like, why did we do that? So it's forever changing. But I think the most important thing is to just relax a little bit around the holidays. I always say that to people because a lot of people feel so much pressure to get the perfect gifts and to go to every holiday party they're invited to. And then suddenly, January comes and you look back on the last couple of months, and you're thinking, "I didn't even enjoy it." There's so much festivity, so much beautiful music and lights and colors and all that stuff that is so joyous and fun and cozy and warm, and sometimes we get to January and we didn't enjoy any of it because we were so focused on what we have to do and all those traditions. So that's one of the important things, letting go of some of those things so that you can enjoy the process of the holiday season. Just because you made a specific cookie every year does not mean you have to do it this year. If that means that you're not going to have as much fun this holiday season, then get rid of those cookies and order some cookies from your favorite place or do something that makes you feel good instead of going to the holiday work party that you don't really want to go to or doing those things that you don't want to do. I think it's so important to just find some time for you and whatever you like about the holidays. Do that and don't be so tied to those traditions just because they're traditions.

OK, I know neither of us can pick just one holiday movie, so what are some of your go-to holiday movies to start the season?

The list is long. Home Alone one, Home Alone 2. Jingle All the Way is unhinged and it makes me laugh every time. It's crazy. Also, in terms of Muppet-content, I'm a huge Muppet fan and I know people love Muppet Christmas Carol, which is flawless. Perfect. We love it. But A Muppet Family Christmas is the one that I have to go back to all the time. And then I'd say Family Stone for the drama. And finally, [National Lampoon's] Christmas Vacation, which really is my book. I really wanted it to feel like the book version of Christmas Vacation. That was the goal. My last book, I heard from a lot of people, there was this family vacation that sort of spanned three chapters, and so many people were saying, "Oh my God, it reminds me of Vacation" or "your family is like the Griswolds" or whatever. It felt so apt because for this book, that's what I wanted. I wanted it to feel like you're watching Christmas Vacation where there's like a little heart and a little drama, but it's a lot of laughs hopefully.

I mean, Family Stone and Christmas Vacation are at the top of my list. I also would say Mickey's Christmas Carol; it's only 26 minutes, but it's incredible. It just gives me everything. But the number one for me, and no one really ever mentions this, is While You Were Sleeping. It doesn't feel like a Christmas movie, but it is a Christmas movie.

There's so many of them. I have a holiday movie podcast, where my co-host and I recap and break down these holiday movies every year. And we keep thinking at the end of every season, we say there's not enough for another season. And then we look at the list and there's so many, some good, some bad. I just watched Little Women, the '90s version, for the first time. It's so warm and cozy. And I became a fan of it after seeing it. I think I had seen it when I was little but seeing it again, as an adult, the '90s version was just lovely.

What is the one holiday food or tradition that you think just absolutely needs to die?

Oh, gosh. Well, I think there are cookies that we could do away with, that become cookies that people just make for traditions. In my family, my mom always does those snowball cookies, and I just think they're a little dry. I like a soft gooey cookie. So I'd say those probably are my least favorite, although I know Linda Pellegrino is not gonna like that I said that. But I'd say get rid of those.

I think maybe meant to be dipped in something. But still, if a cookie has to be dipped to enjoy, is it worth it?

And by the way, I say this as someone who will eat 10 of those in one sitting, so it's not something I will give up or stop eating by any means. I just think if there were other things, I'd pick the other things first,

And that is also the definition of the holidays for me. Just sitting there being like, "I know I don't like this but I can't stop eating it."

There's so much stuff. I like when all the candies come out and they're all seasonal. Here's a trick, I heard you should always buy the seasonal candies at the store because they're fresher. So you never know when the store is putting out Snickers or whatever, but you know that if it's the holiday version, even though this product is the same, if it's the holiday packaging, they're supposed to be they're always fresher.

Listen to H. Alan Scott on Newsweek's Parting Shot. Available on Apple Podcasts, Spotify or wherever you listen to podcasts. Twitter: @HAlanScott