There’s a moment every sober person knows: the pivot from spectacle to humanity. Watching the Charlie Sheen documentary together, our Curator crew kept circling the same question — who was really “winning” during that infamous tour? The hat said one thing; the reality said another.
From the opening minutes, Alysse’s spoiler-friendly PSA sets the tone: we’re not here for reverence; we’re here for truth with sparkle. Early on, the conversation lands on a line about shame — how it can become a North Star, a South Star or a Death Star. It’s the kind of metaphor that hints at deep work, the kind you earn in recovery. But as Dr. Sarah noted, the film seems to flirt with insight while dodging humility. We wanted the “then what?” after the metaphor — the “I harmed people, here’s how I’m making amends,” the gritty specificity that converts slogans into sobriety.
The documentary’s nostalgia pulses — Ferris Bueller’s blink-and-you-miss-it cameo, the Karate Kid what-if. For Gen X watchers, those beats are catnip. Our table laughed, sighed, then wondered about the road not taken: would a tidy blockbuster path have spared Sheen or just typecast him differently?
But the heart of our debate was exploitation. Dr. Sarah can’t shake the stadiums, the merch, the handlers greenlighting chaos because chaos sells. The irony of a “winning” hat atop a man near bottom isn’t subtle; it’s a billboard for what happens when an audience confuses virality with vitality.
Denise Richards became a prism for nuance: love, codependency and the invisible labor of caregiving in public. Our team recognized the tenderness and the traps — how devotion blurs into self-erasure, especially under the glare of early-2000s tabloid culture. Alysse’s compassion for Richards, including her parenting and caretaking, reframed the story away from caricature and toward complexity.
That’s where recovery storytelling must do better. Not with shock-value “reveals,” but with accountability and repair. The doc’s late-act “secret” lands with a thud because it isn’t the point. What we needed wasn’t a salacious twist; it was an honest map of restitution. As Megan put it, insecurity can wear a sly smile, but the amends process doesn’t. It’s unglamorous, tedious and holy.
Still, there were threads worth keeping. The protective power of sports and the quiet loyalty of a friend named Tony — anchors you can tie yourself to when fame becomes a rip current. Even in spectacle, the human need for team and steady witnesses remains. And that’s the paradox: a person can be charismatic, generous, hilarious — and still leave wreckage. Recovery asks us to hold both truths at once.
So what does recovery deserve from celebrity docs? Less montage, more inventory. Less “winning,” more making things right. Show us the phone calls, the repayments, the repaired boundaries, the boring routines that keep people alive and present. Show us the people who stay — partners, kids, Tonys. And show us the ones who walk away to save themselves.
In the end, our table agreed on this: fame can sell the worst parts of us, but it can’t buy the best parts back. The best parts are earned, daily, in rooms without cameras — where humility is the headline and “still sober” is the only brand that matters.
Listen to the full roundtable and bring your take.
Getting sober is one thing—but staying sober? That’s where the real adventure begins.
This show is for you if you’ve ever wondered:
– Where can I find inspiring sober podcasts, apps, and creators?
– How do I give back or stay plugged into the sober community
– What are the best sober-friendly drinks and travel tips?
– Where do I find the good NA drinks that don’t taste like regret?
The Sober Curator is your go-to for sober pop culture, booze-free travel, apps, creators, and community.
We’re not here to help you get sober.
We’re here to help you live sober—and love it.
Therapist, author and media pro Kelley Kitley joins Alysse to unpack “gray area” drinking, stigma around labels and what long-term recovery really feels like — including a visceral craving moment and the simple, honest tools that kept her sober. They also dig into cross-addictions, perimenopause curveballs, parenting teens and how sharing your story (even when it’s messy) can change lives.
Takeaways:
“Gray area” drinking thrives on qualifiers; clarity reduces stigma and increases connection.
Cravings can resurface years in — play the tape forward and “tell on yourself” to your sober network.
Sharing your story can be a professional risk — and a lifeline for others (and you).
Language and identity (“alcohol-free,” “sober,” “alcoholic”) often depend on social circles; choose what supports your recovery.
Perimenopause symptoms can echo old patterns; stack healthy coping tools early.
Key Timestamps:
[02:01] — Alysse’s Chicago intro + Kelley’s “grew up above a bar” backstory.
[06:00] — Media hustle: pitching herself, ”Today Show” bump and making impact.
[09:08] — Making her mess her message: therapist transparency & the book.
[18:32] — A real-time craving in a hotel — and the group text that saved the day.
[34:23] — Labels, stigma and the “gray area” short film.
[27:26] — Perimenopause, rage, sleep and staying out of old habits.
Resources & Links:
-Kelley Kitley: Website, Instagram, LinkedIn, Facebook
-Book: ”MY self: An autobiography of survival”
-TEDx: ”I show my scars so others know they can heal”
–The Kelley Kitley Podcast: America's Social Worker Unfiltered
-YouTube: ”Gray Area”
–Alcohol + Substance Use Disorder Guide
–Recovery Nonprofit Resource Guide
–LBGTQ+ Recovery Resource Guide
Connect with Us:
-Website: www.thesobercurator.com
-Facebook: @The Sober Curator
-Instagram: @thesobercurator
-YouTube: @thesobercurator
-Pinterest: @thesobercurator
Follow & Subscribe:
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If you have a story, feedback, or just want to connect, email us at thesobercurator@gmail.com. We’d love to hear from you!
About:
Sobriety isn’t the end of the party—it’s just the start of a better one. Hosted by Alysse Bryson, media powerhouse and sobriety’s ultimate hype woman, and joined by Sober Curator contributors, The Sober Curator Podcast* delivers bold convos, pop culture deep dives, and zero-proof living that doesn’t suck. Whether you're sober, sober-curious, or just looking for good vibes without the hangover, we’ve got you covered. Subscribe now—because getting sober matters, staying sober matters more.
*The Sober Curator Podcast is a space for open and honest conversations about sobriety, recovery, and alcohol-free living. While we celebrate all paths to a sober lifestyle, some topics discussed may be sensitive or triggering for certain listeners. This podcast is for informational and entertainment purposes only and is not a substitute for professional advice. If you’re in recovery or exploring sobriety, please take care while listening and seek support from trusted professionals as needed.
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MOVIE NIGHT REVIEW: Charlie Sheen’s Documentary Exposes a Man Still Chasing His Addictions
aka Charlie Sheen | Official Trailer | Netflix
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