Step right up – Jimbo the Drag Clown is here! The Clown of the North joins TS Madison in the “Outlaws” ring, and they kick things off with a look back at her “RuPaul’s Drag Race: All Stars” Season 8 win. Maddie floats the idea of an Olympic-style competition for every past champion. Not just a few, but ALL of them. We NEED to see this pantheon of Queens united– but unfortunately, as Maddie and Jimbo recognize, not everyone would be here to return. Madison and Jimbo pause to honor their beloved sister The Vivienne, who left us far too soon, which inspires a conversation about Jimbo’s sobriety journey. 

Jimbo takes us through her origin story and how embracing her queerness changed her life. She talks about her complicated relationship with her father, who she remained estranged from until his deathbed, and the difficult realization that goodbye’s don’t always look like they do in the movies. 

Next, we’re traveling back to the start of the COVID-19 lockdown– which just so happened to coincide with Jimbo’s debut on “Canada’s Drag Race.” Jimbo talks about the initial stress of watching the world shut down during her moment in the spotlight, but how, in a way, this turned out to be a blessing in disguise. When the world gets dark, we want to laugh, and Jimbo says she still meets people who tell her she helped get them through 2020!

Of course, “Drag Race” was just the beginning. Jimbo shares how her All Star’s winnings helped her produce her dream project, “Jimbo’s Drag Circus” and her plans to take her clowning to the big screen. Madison and Jimbo agree, everybody’s got a clown in them! (Well, at least Maddie did once upon a time…)

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

Is it on? Is it on?? Honey, is this thing recording?! TS Madison broke the Internet with six seconds and a 22-inch weave. And she didn’t just go viral — she became part of the culture, from “RuPaul's Drag Race” to Beyoncé’s “Renaissance.” Her superpower? Her voice. Her kryptonite? Doesn’t exist. Her podcast? The one they never saw coming. 

Each week on “Outlaws,” Madison sits down with living legends and rising stars who shed their armor and own their stories — turning side-eyes into sermons, pain into punchlines, and grief into galaxies. They speak when silence is safer. They dream when told to disappear. And they know what so many are taught to fear: that when you speak your truth, you open a portal.

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Hello, Outlaws Listeners! We want to share a podcast we think you might enjoy, HIGHKEY! with Yvie Oddly and Ryan Mitchell!

Welcome to HIGHKEY! — the boldly queer pop culture party you didn’t know you needed. Hosted by RuPaul’s Drag Race winner Yvie Oddly and culture critic Ryan Mitchell, HIGHKEY! is where chaos, comedy, and the realest conversations collide.

It’s like eavesdropping on the funniest, most unhinged, and surprisingly heartfelt side convo at the party — with past guests like Laverne Cox, Rico Nasty, Bob the Drag Queen, and Lena Waithe, plus more queer icons on the way. Follow the fun @highkeyhere on Instagram, TikTok, and YouTube, and subscribe wherever you get your podcasts. 

Listen here and subscribe to HIGHKEY! with Yvie Oddly and Ryan Mitchell on the iHeartRadio app or wherever you get your podcasts! 

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There are few in this world that are as controversial, raw, and authentic as TS Madison AND own up to it– and today’s guest is one of them. For a conversation all about sexuality and power, Maddie is joined by Cherry Thee Boom!

Don’t get it twisted– TS Madison is all about uplifting the girls! Cherry might be a humble country girl at heart, but she IS that girl, with her very own podcast, “Cherry on Top”, and an upcoming book, “Black Butterfly Rising”. And in her introduction, Cherry reminds us that people are ALWAYS going to criticize you but that’s no reason to dim your light!

We’re shaking the table this episode, as Madison and Cherry share their experiences with sex work and navigating the world as Black trans women. Cherry shares her philosophies on men, romance, and sex, and the advice she received when she first started her transition. The pair talk jealous from cis women, intercommunity hostility, and the purpose of labels. And we’re breaking down what really makes a DL man. Neither Maddie or Cherry is known for holding back, and they’re not starting now. And this episode reminds us, the girls are tired! 

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

Messy Monday? Meet Talk Your Sh!t Tuesday! This week, Maddie chops it up with writer, actor, sexual/mental wellness advocate, and fellow iHeart podcast host Brandon Kyle Goodman!

Reunited for the first time since the GLAAD Award nominated Logo Legend special where BKG and friends gave Maddie her flowers, they’re picking up right where they left off. Brandon’s talking all things gay, nonbinary, and polyamorous… and what it’s like to navigate those identities in today’s political climate. 

Madison and Brandon reflect on their intersecting identities of being Black, queer, and trans, and how those identities show up in the entertainment industry. Brandon shares the joy of working on “Big Mouth,” a show which they say championed the importance of diversity of all kinds in the writers room. But shows like “Big Mouth” are more often the exception than the rule, and Hollywood still has a lot of work to do to make sure everyone is seen and heard– on screen AND in the writers room.

Brandon shares pivotal moments from their own life, including how “Sister Act 2” inspired their creative journey and how their mom became a Born Again Christian, sparking Brandon’s villain era. But, as they remind us, sometimes you need to be the villain in someone else’s eye in order to live your authentic life.

In a time when there’s incredible pressure to conform, Brandon asks us, who would you be if society never got its hands on you?

To hear more from Brandon Kyle Goodman, check out Tell Me Something Messy on the iHeartRadio app, Youtube, or wherever you get your podcasts.

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

Ask and you shall receive! This week’s guest is our #1 most requested—by a landslide—LUENELL! Amid her nonstop touring schedule, she blesses the "Outlaws" studio to chop it up with TS Madison, and listen… we’re already nominating this episode for the "Outlaws" Hall of Fame.

First, Luenell dives into her roots in small-town Arkansas and why she goes by just one name. From there, the conversation takes off: her wild bank robbery story (and how she got caught), a brief stint as a sex worker, why she was unable to watch Princess Diana’s funeral, overcoming addiction, and the surprising ways prison taught her to appreciate life’s little things.

We also get a behind-the-scenes look at her illustrious comedy career, working with fellow legends like Adam Sandler and Eddie Murphy—whether that’s hanging upside down on a stripper pole or voicing cartoon characters with the "Hotel Transylvania" franchise. Plus, Luenell spills on reconciling with Leslie Jones while filming "Coming to America 2."

Madison and Luenell also unpack Hollywood’s brutal beauty standards, how a surprise FaceTime from Rihanna landed her a Savage X Fenty modeling gig, and how that experience paved the way for her (now retired) OnlyFans.

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

Today, we’re joined by the Queen of Melrose herself, Cosmo Lombino! Owner of Cosmo's Glamsquad, Cosmo & Donato, and Fashion Whore, Cosmo has styled everyone from celebrities to the girl next door– and of course, our host TS Madison! Maddie and Cosmo reminisce on their first meeting in one of Cosmo’s shops 15 years ago… and the shoes Maddie still needs to pick up…

Cosmo’s bringing Melrose to the studio, with a Medusa-esque headpiece perfect for Madison. And let’s hear it for the kimono! Could we be seeing an on-site Outlaws styling sesh in the future??

From fur coats one week to food stamps the next, Cosmo gets into her Scorsese-esque childhood in the Bronx. Maddie asks the big questions like, can you be a crime boss and a Jehovah’s witness? And of course, we dive into the story of her family’s move to California, which went viral in 2024. 

Family is a big theme of this episode, as Maddie and Cosmo share their own journeys with their families and why it’s important for parents to love their gay children. God loves his girls and God loves his gays– don’t get it twisted! 

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

Today, TS Madison is joined by YouTube royalty– actress, model, philanthropist, and mother of 3 (cats), Gigi Gorgeous!

Maddie starts the conversation by coaching Gigi on how to talk her shit! She IS that bitch! The pair talk about the early days of YouTube, and how being in the right place at the right time led to Gigi’s iconic billboard on Sunset Boulevard. Maddie talks about admiring Gigi as one of the ORIGINAL rich trans girls on the Internet, and seeing her as a model of success early on in both of their careers.

But it’s not all LA sunshine and lipgloss– Maddie and Gigi get into the nuances of being trans icons, from the competition within the community to the pressures to be the perfect role model to the extra barriers trans women of color must face. The girls get into navigating dating, chasers, and how the community keeps itself safe!

We get a glimpse into some key moments in Gigi’s life– including how she went from being a diving champion to a makeup guru, her villain era as what she dubbed “the city gardener”– and of course, being detained and nearly imprisoned in Dubai. 

And for the first time in “Outlaws” history, for Ban it, Bitch, we’re banning a ban: Gigi says young broke trans girls deserve the right to shoplift!

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

We’ve got a true queer power couple in the studio today: THE Raven-Symoné and Miranda Maday, co-hosts of the hit podcast Tea Time! Raven’s been in the spotlight since diapers, but don’t get it twisted – Miranda is every bit a powerhouse herself, with an Emmy to boot.

Nothing’s off-limits in this conversation. We’re tackling the biggest (and girthiest) questions about strap-ons: Raven wants to know, why pink? Madison counters, why not? And are “flesh-tone” strap-ons outdated—or still the ultimate hipwear??

Raven gets candid about growing up under the Disney microscope, the pressures around gender identity and presentation, and how meeting Miranda changed everything. In just 38 minutes, this episode covers so much ground—from why entertainers get paid so much, to what it’s like navigating private pain while in the public eye, to why the powers-that-be are so terrified of social media. And of course, what it actually means to represent the LGBTQ+ community (or as they call it: the Labiquita!) as public figures.

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

For this episode of Outlaws, TS Madison is joined by the QUEEN of comedy herself, Mo’Nique!

These girls go way back, and Mo’Nique shares a story about her and Madison’s first interview together. The pair talk about their respective journeys to stardom and navigating Hollywood as plus sized girls. Whether your trans or cis, there’s a lot of pressure to change who you are, but Mo’Nique isn’t having it. She reminds us that the public fell in love with THE TS Madison as she is, loud, live, and in COLOR!

Next, Mo’Nique spills about her relationship with her husband Sidney Hicks, and how she fell in love with her best friend. She talks about how this relationship has opened up new ways of seeing herself, and what she deserves– and what we all deserve from love!

And of course, neither our host or our guest today shies away from controversy– sometimes on opposite sides. We get a peak behind the scenes at how TS Madison helped reconcile Mo’Nique and Lee Daniel’s working relationship. And we’re all winning because of it! Could we see more TS Madison-facilitated reunions in the future? Could we see a conversation between Mo’Nique and Oprah? Or Tyler Perry? Mo’Nique and Maddie say the door is open!

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.

With a multifaceted career both onscreen and behind the camera, Orlando Jones is the definition of a storyteller. And he’s no stranger to being called an outlaw– from "Mad TV" to Mr. Nancy, Orlando’s been shaking things up since the 90s! 

To start off, Orlando tells TS Madison about his evolution in the entertainment industry. An early adapter of mobile media content, Orlando’s media company won the first ever virtual reality Emmy Award. Next, they get into the nuances of centering Black voices in entertainment– storytelling is a powerful tool, and Orlando wants to see more stories by and for Black America! 

And of course, we have to get into the “American Gods” of it all. Madison thanks Orlando for his work shaping the show’s iconic, Mr. Nancy– not only playing the character on screen but developing the character in the writer’s room as well! The pair talk Mr. Nancy’s iconic monologues, the show’s reimagining of spirituality and mythology…and of course get into the details of Orlando’s controversial firing from the show– which prompted fan backlash and boycotts of the show’s third (and ultimately final) season.

That’s not all– in an exclusive moment, Orlando Jones reveals he’s just finished a Mr. Nancy novel! Could we see a role for TS Madison if (and when) it’s ever adapted for the screen???

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

See omnystudio.com/listener for privacy information.