February 21, 2025, 10:21am
Photo by Mindy Tucker
Telling a good, smart joke about immigration is hard. Not only is it a fraught and complicated topic, but it’s a space that’s overstuffed with bad, right-wing attempts at comedy. Too often immigrants are the targets of mean-spirited jokes by hacks — as comedy writer Felipe Torres Medina told me, “a lot of jerks are already making fun of these incredibly brave people and most of them have jobs in the current administration.”
Felipe should know, as an expert in both joke writing and American immigration. The Colombian writer has been working in comedy for years, widely publishing short humor before landing a job at The Late Show with Stephen Colbert. Next month he has a new book coming out, which tackles head-on the labyrinthian process of becoming American.
America, Let Me In: A Choose Your Own Immigration Story is a satirical and at times serious look at the US immigration system. The book’s choose-your-own-adventure elements involve exploring “a multitude of possible immigration stories,” guided by the reader’s choices: are you a model? Do you have an EB-5 Investor Visa? Do you know who The Smiths are? Some of the fictional outcomes are silly, some are poignant, and some are drawn from Felipe’s own experiences.
The book is also a lot more informative than I would have guessed, something that comes from the pressure for immigrants to have an “encyclopedic knowledge of the immigration system to know what your options are,” as Felipe put it. Amongst the humor, there’s a lot about specific immigration forms, processes and terms — the glossary in the back has some of my favorite jokes in the book.
I talked to Felipe over email about his forthcoming book, his literary inspirations, and what it’s like to write comedy right now.
The interview has been trimmed from our original conversations for clarity and length.
Tell me about the origin of America Let Me In — when did you first start thinking about the idea that would become the book?
I got the idea for the book sometime in 2017. I moved to the U.S. in 2013 for school and by the time I had this idea, I had already navigated getting or attempting to get three or four kinds of visas. When you’re an immigrant and you’re trying to remain in the country and you’re neurotic like me, you have to acquire this sort of encyclopedic knowledge of the immigration system to know what your options are.
2017 was a very strange time for immigrants because Trump had so obviously made immigration the key to his campaign and people had, after eight years of Obama where liberals mostly ignored the subject, come to learn that it is 1. a huge issue, and 2. full of contradictions. It was a period of time where I found myself explaining to all my American friends just how hard and expensive it is to move here “the right way.”
So, in a mix of frustration and inspiration I decided to try to write a how-to guide about immigration but actually make it funny.
I’m not sure a lot of people look at the American immigration system and think “comedy goldmine” — were there moments from your own immigration that struck you as funny or sparked your comedy brain?
Yes! The immigration system is so chaotic and insane that it is inherently funny. For example, because I am Colombian, before I even moved here, my family and I had to apply for a tourist visa as a teen to come to the U.S. because we wanted to go to Disney World. When you’re filling out the online questionnaire that starts your application (you later have to go to an in-person interview at the embassy) the questions can range from “What’s your name?” and “What’s your address?” to “Have you ever been a part of a terrorist organization?” and “Have you ever participated in genocide?”
The tonal shift is funny in and of itself, but I remember as a teen growing up in the middle of the Iraq War and the War on Terror, picturing the members of ISIS or Al Qaeda filling out the form to try and enter the U.S. to do some terror attacks and being like “Ope! They asked the question if we’re terrorists. Guess we gotta answer honestly! Agh, we were so close!”
There are a lot of layers in this book: there’s obviously tons of comedy, but there’s also some stuff that feels pulled from your own life, as well as some grounded and not-fully-tongue-in-cheek explainers about our immigration system. How did you balance humor, memoir, and explanation?
My main goal was to always write a funny book. That was going to be the thing that would make this book actually enjoyable to me and, I think, to the reader. The immigration system needed explaining, but I knew I had to make it funny because otherwise talking about immigration is at best dreadfully boring and at worst depressing/rage-inducing.
I also knew from the beginning I didn’t want to write a memoir because I have huge respect for the genre and very little respect for my life’s story. I just don’t think I’m that interesting. I’m not Carrie Fisher or Prince Harry. Like, those are people who’ve had interesting lives. I, for the most part, tried to move to America and succeeded. That’s it.
That said, once I realized I was going to tell a lot of stories about immigration, I understood that telling mine would be important because there were many humorous things that happened to me in my journey.
Why a choose your own adventure? Did you read those books as a kid?
I did! I grew up in Bogotá, Colombia, but my school had a great library stocked up with a lot of books in English. We had two Choose Your Own Adventure books for a whole class of 103 students, so it was always a battle to get them. I remember liking them, but not enjoying a book that killed me within a few pages. So while I played with them, I think I very quickly got over them and went back to my Tintin books.
However, the format came back to my life in my last year of high school when I read Julio Cortázar’s Rayuela (Hopscotch in English.) In that book, Cortázar encourages the reader to read in an order jumping between passages and parts of the book as you would when playing hopscotch. I was a Latin American kid deeply immersed in the literature of the Latin American Boom writers and reading this was one of those “Oh wow, I didn’t know that you could do this!” moments you have as an artist.
What were some of your inspirations working on this book? What other books or authors did you have close to mind while writing?
When I write I imagine all the great writers that have come before me. I imagine flipping William Shakespeare off and saying, “You couldn’t do this, baldy,” as I drive past him in the convertible I bought with my royalties money.
Seriously, great humorous writers were always my inspiration for this. My comedic education came by way of Simon Rich and great contemporary satire writers like Alexandra Petri, but I am also a huge fan of Vonnegut and George Saunders who are able to—much more successfully than I could aspire to—blend humor with pathos and talk about “serious” issues in texts that are laugh-out-loud funny. I also don’t think I would’ve started reading and writing humor if it weren’t for Tina Fey’s Bossypants, The Daily Show’s America: The Book, and Stephen Colbert’s I Am America (And So Can You!).
As I read and researched the book, I also read Georges Perec’s The Art of Asking Your Boss for A Raise and Ellis Island and some Latin American writers who worked around multiple paths and choices like the aforementioned Rayuela by Cortázar and the works in Borges’ Ficciones, specifically stories like “The Garden of Forking Paths” and “Pierre Menard, Author of the Quixote,” which is very funny.
As I struggled with finding some sort of conclusion to this book in the wake of the 2024 election (which was just about starting when I finished my manuscript) I found it very useful to read David Mitchell’s Unruly, which is a history of British kings. I love Mitchell and his work from his sketch shows, his sitcoms, to his columns on The Guardian, and while I read this book as a little treat to myself (History??? Written by a comedian I love??? Papa like!) I ended up really enjoying the introduction and conclusion to the book. I liked the parts in between too! But reading that really helped me ask myself why I believed moving to America was an endeavor worth pursuing.
It is very Samuel Adams of me that it took a Brit’s perspective on English kings to make me be able to elucidate why the United States is an experiment worth fighting for.
I know you’re originally from Bogotá, and I’m curious what funny writing you grew up with. What is the Spanish language prose comedy world like?
The Spanish-speaking world is immense and as such the comedy culture in each country is different. Sadly, humor writing and comedy in Colombia is not great. There was one great satirist in the late ‘90s and early 2000s, named Jaime Garzón. I remember my dad watching him every week as he lampooned politicians and celebrities, and I tried to do the same as a kid. Sadly, he flew too close to the sun in a country that was, at the time, plagued with political violence and a deadly drug trade fueled by Americans’ unending appetite for cocaine, and was murdered by a right-wing death squad.
My dad also showed me an incredible, hilarious Argentine musical comedy troupe called Les Luthiers, who I can best call the Latin American Monty Python. They are incredibly formative for me and for many Latin Americans.
I don’t want to spoil anything, but toward the end of the book, there’s a moment where you draw a line and say that there are some things that you don’t want to make light of. In general, is the line between what you want to joke about and what you don’t pretty firm? Or is it more contingent?
I don’t like to draw huge lines in the sand about what can and cannot be funny. I think that is counterproductive, but as I say in the book, I think the stories of migrants who come here walking through the jungles and deserts of ten or more countries aren’t really comedy fodder. A lot of jerks are already making fun of these incredibly brave people and most of them have jobs in the current administration. I think those stories are important and should be told, but the tone of the book would not do the stories justice.
You were working on this book during some—to put it lightly—big years for the immigration debate in this country. Did the book, or the way you thought about the book, shift as you were writing?
The reason I wanted to write this book is because I feel like people talk about immigration but have no idea what they’re talking about. So the book wouldn’t exist if immigration weren’t a huge debate in this country. If Obama had successfully passed DACA, if Congress under any administration had any real intention of creating comprehensive immigration reform, immigration probably would not have been the subject of my first book.
That said, I would rather the book be unimportant or passé or even non-existent if it meant the lives of immigrants were easier than it is right now.
When you’re working on something topical, whether it be for TV, or for McSweeney’s, or for your book, who do you imagine as your ideal audience? What do you hope people take away from your satire?
I try to write things that will make me laugh. That is always the first directive. I don’t think I really try to look for an audience for satirical humor. However, the ideal audience for my book is a very rich person who will like it so much, they will buy millions of copies of it.
How does it feel to be an American, an immigrant, and a comedy writer these days? How are you doing?
I’ll get back to you when I am an American. I don’t have U.S. citizenship yet; I am merely a permanent resident. That means I have a green card, which is better than a visa. I know these terms are confusing, but if you want to understand all of this, I have a great book for you.