Making waves on social media as a captivating on-air personality and comedian, Ali Weiss, hosts conversations around drugs, sex and pop culture through her niche anonymous confessions podcast, Tales of Taboo. In a world where some are still wary to touch on these matters, Ali chooses to spearhead them, through real, funny and uncontrived stories.
Weiss creates a safe space for her listeners, not just through anonymity, but through the humble honesty of her own experiences and confessions – such as her abortion, sexual mistakes and getting kicked out of her sorority – allowing no given topic to be off the cards. Her ability to humanise such stigmas through humour and relatability breaks the conventional boundaries between typical podcast hosts and listeners.
Occasionally, public figures with unconventional lives are invited on to the show to encourage more confessors to submit entries. Past guests include reality TV stars Whitney Port and Katie Maloney, obituarist Adrian Dannatt, and mind-reader Jason Suran.
Ali is the best friend you never had, but always wanted. She is outrageously funny, invigoratingly candid, and dedicated to educating around controversial subject matters.
We talk to Ali about her upbringing, interviewing renowned whistleblower Edward Snowden and her most memorable episode to date…
Listen to the latest episode…
Read the exclusive interview below…
You’ve been described as the “Princess of Taboo” – can you tell us more about what that means to you, and how you incorporate taboo subjects into your work as an on-air host, comedian, and writer?
I grew up in downtown Manhattan, a block away from the circus that is Washington Square Park. I’ve always been a very curious, adventure-hungry girl and, admittedly, a loudmouth, but I never identified as ‘edgy’. Like, I had neurotic Jewish parents and a Bernedoodle and studied theatre in college! So it was strange when I entered the entertainment industry and was immediately perceived that way by brands and casting directors. I think for women, up until recently, there was a conflation between honesty and/or shamelessness and edginess. I dreamed of booking Dove commercials and supporting roles in teen dramas on the CW, but instead, I was offered opportunities to talk about sex and weed; I didn’t understand why I couldn’t make dirty jokes and be a “nice girl” at the same time.
I felt a lot of pressure to conform to the way I was perceived: I figured, if these industry professionals see me as tough and sexy, and my Instagram followers respond best to that type of content, I guess that’s who I am. So I pivoted away from acting and towards being a host/talking head, creating content and rebranding more times than I can count. I had a lot of identity crises throughout my early and mid twenties, but the older I got, the more I recognized what a huge privilege it was to start difficult conversations, using humor, with very few repercussions. Sure, people have judged me harshly on social media, but I’m a white woman in a liberal city who will not be ostracized by my family or lose my job for speaking out about, say, having an abortion (which I do not regret) or some of my more regrettable past decisions with drugs and alcohol. I get to be a voice for people who feel like they don’t – or can’t – have one. I finally decided to claim that power and privilege, and branded myself as the Princess of Taboo.
Your podcast, Tales of Taboo, has covered a wide range of subjects, from fashion and sex work to drug dealing and Title 1 public schools – can you tell us about a particular episode that resonated with you, and why?
My best friend’s father died from cancer in 2021, and I wanted to do something for him and his mom that would be more helpful than just saying “I’m sorry” or bringing junk food to a Shiva. So, I put out a casting call for anonymous contributors who had lost loved ones and gained wisdom about how to deal with grief. The outpouring of stories was so moving – I sobbed the whole way through producing that episode. Death is the ONE thing that every single human has in common and yet, since nobody wants to talk about or even acknowledge it, it’s the most isolating. I was heartbroken to hear so many contributors say this was the first time they’d ever had an outlet to publicly express their sadness. That experience really expanded my definition of what a ‘taboo’ subject is.
You’ve interviewed everyone from political figures like Edward Snowden to reality TV stars like Whitney Port – how do you connect and prepare for such a diverse range of guests, and what makes for a successful interview in your opinion?
The most engaging interviews are fluid conversations, not call-and-responses between a subject and an ass-kissing or self-righteous journalist. I call myself a storyteller and conversationalist rather than ‘journalist’ because my job is not to report, it’s to connect. When interviewing celebrities, I try not to take them (or myself) so seriously. Snowden came on my show with PleasrDAO
You’ve traveled through subcultures across America, from right-wing political rallies to forest raves – what have been some of the most eye-opening experiences you’ve had, and how have they influenced your work?
I went to a Quaker school from Kindergarten to graduation; rode the subway alone by the time I was 10; was in nightclubs with all sorts of wild characters at 15. I went to galleries, read the Times, hung out with semi-famous bands, watched my peers go to rehab and jail – I thought I had experienced the whole world growing up in New York. What a moron! The moment I set foot on my college campus in California and could count the amount of friends who’d traveled out of the country on one hand and friends whose families didn’t own guns on the other, I realized I actually knew nothing about the real world and that, in fact, New Yorkers were the delusional ones. Coupled with my disinterest in following the traditional path of getting engaged by 30 and working in medicine, law, or finance, I became obsessed with stepping (or driving, or flying) out of my upper-middle class bubble as often as possible, and investigating how the majority of America defined ‘happiness’ and ‘success’.
All of my adventures have, as the kids on TikTok say, altered my brain chemistry, although the most fun I’ve ever had was throwing dead fish across the Flora-Bama border at the annual Interstate Mullet Toss
How do you balance the comedic and provocative aspects of your work with the need for sensitivity and empathy when tackling difficult subjects?
Part of being a comic is finding the humour in dark situations; humour (especially when it’s at your own expense) is also the quickest way to bring people together, relax them, and earn their trust. That said, it’s important to read the room, even if the people in it can’t physically be seen. I don’t get rattled or offended easily, but that’s not true for everyone, especially when they’ve been through something traumatic. I always attempt to put my confessors’ and listeners’ feelings in front of my desire to land a joke.
What impact has your podcast Tales of Taboo had on you as a person and what impact do you hope it has for your listeners?
As the saying goes, “the opposite of love isn’t hate – it’s indifference.” I’ve come to realize that when people react strongly or negatively to foreign ideas or experiences, it often stems from fear. My job is to help people realize that things are only scary or strange or “bad” until you attempt to understand them. Not everyone is going to listen to an episode about sex work and immediately think that escorting
How do you think the entertainment industry is evolving in terms of representation and diversity, and what role do you hope to play in that evolution?
It’s a big relief to finally see a wider variety of races, sexual orientations, bodies, and overall physical presentation in the media, but diversity of imagery does not necessarily equate to diversity of storytelling. There’s still a strict set of rules that have to be followed in order for a person or their POV to be seen as ‘agreeable’ and marketable to the masses. A tremendous amount of prejudice still exists against the experiences of minorities, women, queer folks, transgender folks, sex workers, addicts – I could go on. It baffles me that we live in a culture where it’s more socially acceptable to lie in order to create a marketable image than it is to be upfront about one’s less-common choices, so-called ‘imperfections’, or ‘disagreeable’ traits.
My podcast is special because anybody can contribute to an episode if they’ve had the life experience I’m casting for, and the anonymous, color-blind, (mostly) genderless format means I can amplify multiple categories of lesser-heard voices at once.
You’ve been a guest on several popular podcasts, like Whitney Port’s “With Whit” and Betches’ “Diet Starts Tomorrow” – how do you approach being a guest versus being a host, and what are some of your favorite podcasts to listen to?
A lot of confessors trust me with their secrets – many of which they’ve never told anyone before – because I’ve been willing to air out my own ‘dirty laundry’ first. It levels the playing field, and lets them know that they’re in safe, nonjudgmental hands. It’s also cathartic for me to share my darker experiences with people who I know will not judge me either. But talking to myself for a full hour in a solo episode feels weird – I’d much rather spill the beans through a two-way conversation on someone else’s show. I love being challenged, so it’s really flattering when another host takes the time to do research on me and prepare thoughtful questions. Equally, I love to just shoot the shit and laugh and talk about my drunken antics instead of serious stuff all the time.
In terms of what I listen to – I’m absolutely obsessed with Ear Hustle, as well as a podcast called This Jungian Life, where three shrinks sit around analyzing dreams and debating, like, ethics and big-picture questions. (Amazing to listen to while stoned.) I obviously ride for Terry Gross, and I also appreciate what Emily Ratajkowski and Dua Lipa are doing with High Low and At Your Service. Most celebrity podcasts are so fucking boring and self-aggrandizing; both women, aside from being sexy, seem down-to-earth and smart.
You’ve worked with companies like Vice, Playboy, and A&E – how do you choose which projects to take on, and what do you look for in a potential collaboration?
Truthfully, there’s nothing I love more than working for somebody else. Content creation can be incredibly lonely- as a former theatre kid, all I want is to go to set and have a director yell at me until eventually patting me on the head and telling me I did a great job. Being surrounded by a creative team is such a joy, and I’m pretty open-minded when it comes to collaborations. Hit me up!
What’s next for you in your career, and what are you most excited about? Are there any upcoming projects or collaborations you can tell us about?
As an experimental IRL version of the podcast, I recently started a ‘salon series’ at my apartment: I curate groups of interesting, forward-thinking women to come drink wine and talk off-the-record about highly controversial subjects – then brainstorm how to create social change. Watching total strangers from very different backgrounds (many of whom I found in niche corners of the internet and cold-emailed with invites) willingly come into my home and open up to each other has been insanely inspiring. I want to start doing this in a larger venue as a public, ticketed event. I’m also working on an essay collection and live show concept about my experiences with strangers – I’m really eager to get back to my roots of performing on stage, and reveal more of my OWN Tales of Taboo. If you live in or near New York, come through.