Sasso, Will
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Sasso opens by explaining why he never pursued stand-up comedy despite loving the art form and growing up on Carlin, Pryor, and Gilda Radner albums: he sees stand-up as requiring a raw, sustained personal exposure of one's own opinions and voice that doesn't suit him, in contrast to acting and character work, which he loves precisely because it lets him disappear into an "illusion" rather than reveal himself directly — a distinction he draws explicitly against performers who jump into stand-up late in a career already built on other recognition, versus lifers doing open mics for over a decade purely out of love for the form. He discusses his impressions work (developed on MADtv alongside contemporaries like Frank Caliendo), explaining that a convincing impression requires only enough of a person's external mannerisms to sustain the "illusion" for an audience, and that deliberately having a caricatured character say things the real person never would makes it funnier rather than breaking the spell; he recalls struggling for a full week to get a competent Michael Caine impression during his first MADtv season, in contrast to more natural fits like his Curly Howard, where he found himself unconsciously visualizing entire scenes "in black and white" as the original Three Stooges before shooting, describing it as a form of channeling built from having absorbed an unusually complete stylistic "blueprint."
Sasso is candid about his own mental health, describing a family history of depression, having initially resisted medication before eventually starting it (recalling an immediate, almost startling sense of relief — "doors and windows were opening" in his brain), and ongoing talk therapy, while advocating for removing the stigma around psychiatric treatment. He discusses friend and MADtv castmate Bobby Lee's public struggles with addiction and mental health with warmth and humor, and reflects at length on Robin Williams' suicide, calling him "the Jesus Christ of depression" — someone whose outward success didn't protect him from being "tortured" internally — and connects this to a broader belief that some degree of instability or "crazy" (which he rates himself as simultaneously a "10" and a "2 or 3," depending on which aspect of himself is in question) is bound up with comedic talent. He also describes a persistent, self-critical inner voice that shows up even after seemingly successful appearances (including feeling he'd "wasted everyone's time" after a well-received MIT lecture), framing this discomfort as possibly inseparable from being a working creative person rather than a problem to be fully solved.
On his current podcast Dudesy, Sasso explains its premise: a company approached him and co-host Chad Kultgen with a proprietary AI that, after being given access to extensive personal data (email, browsing history, and more), generates weekly episode premises and segments for the two of them to riff on — a setup he says paradoxically liberates him from the anxiety of unstructured long-form conversation by supplying absurd, ready-made constraints to react to, rather than requiring him to invent the "weird" himself. He and Lex debate whether AI will ever be able to fully replicate a person's essence or achieve genuine sentience: Sasso is skeptical that uploading consciousness is possible or that AI-generated art will ever mean as much as human-made art (since art's value for him is tied to the artist's lived backstory and struggle), while Lex argues language models are already displaying signs of understanding concepts rather than pure mimicry, and that a curated summary of a person's memories, humor, and quirks could someday convincingly preserve their "essence" even without literal brain uploading — a point Sasso finds persuasive enough to want to relay back to his co-host Chad, who holds more maximalist views about AI and is signed up for cryogenic preservation.
Elsewhere, Sasso discusses the emotional intimacy and impermanence of working on film and TV sets — comparing the bonds formed with a temporary "TV family" to those of actors who fall in love on set, and the discipline required to compartmentalize and move on once a project wraps — and reflects fondly on Planes, Trains and Automobiles as capturing loneliness beneath comedy (particularly through John Candy's character), a theme he connects to a personal anecdote about a lonely late-night waitress in Las Vegas. He discusses pro wrestling as a beloved comfort and "complete escape" (naming Bret Hart as the greatest in-ring performer and Hulk Hogan as his childhood Superman figure), and closes with reflections on gratitude for a stable, low-drama upbringing by immigrant Italian-Canadian parents, advice to young people to pursue what they genuinely love rather than career strategy, and a closing invocation of Hermann Hesse's line from Steppenwolf — "learn what is to be taken seriously, and laugh at the rest" — while admitting he personally still takes far too much too seriously.
Excerpts
On why he never pursued stand-up comedy despite deep respect for it:
“I love the illusion of what I get to do in entertainment... but to stand up there, for me, it's like it would have to all be fantasy... I don't want people to know my opinion, and that's another thing about stand-up.”
On what he says medication did for his depression after years of resisting it:
“It felt like doors and windows were opening literally in my brain. I took a three-hour nap the first day... I'm not a nap guy, I can sleep three hours and I'll be fine, but I took a long nap and then it started to help.”
On why he believes AI-generated art can never fully replace human-made art:
“Art is a connection between people... when you look at a beautiful painting or a sculpture, you're seeing the humanity of the person that brought that painting to life... without the human being there to make it, it's not worth as much.”